JP2007262089A - アミノ置換カルボ糖の製造方法 - Google Patents
アミノ置換カルボ糖の製造方法 Download PDFInfo
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- JP2007262089A JP2007262089A JP2007179423A JP2007179423A JP2007262089A JP 2007262089 A JP2007262089 A JP 2007262089A JP 2007179423 A JP2007179423 A JP 2007179423A JP 2007179423 A JP2007179423 A JP 2007179423A JP 2007262089 A JP2007262089 A JP 2007262089A
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- 0 CCC1C=*C(C)CC11CC1 Chemical compound CCC1C=*C(C)CC11CC1 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Saccharide Compounds (AREA)
Abstract
【解決手段】2-アザビシクロ[2.2.1]ヘプタン誘導体を出発原料として使用するアミノ置換カルボ糖の製造方法。
【選択図】 なし
Description
Chem. Pharm. Bull., 日本, 1991年5月, Vol. 39/No.5, p. 1112-1122 Tetrahedron Lett., 1989年,Vol. 30/No.13, p. 1645-1648
しくは(I')の生成物は、一般式
の生成物のビスヒドロキシル化により得られることができる。
のホモキラルなアミンと、好ましくは塩酸のような無機酸、ホルムアルデヒドおよびシクロペンタジエンとの間のディールス・アルダー反応により得られることができ、当該反応はラーセン(S.D. Larsen)とグリエコ(P.A. Grieco)、J. Amer. Chem. Soc.、107、1768-1769(1985)に記述される条件下で実施される。
-ジメトキシコハク酸を使用することがとりわけ有利である。
式:
の生成物に変換され得る。
の生成物に酸化される。
酸塩、あるいはN-メチルモルホリンオキシドもしくはトリエチルアミンオキシドのような有機三級アミンオキシドから選ばれた酸化剤の存在下、RuO2もしくはRuCl3のような前駆体からその場で場合によっては発生され得る酸化ルテニウム(RuO4)により実施され、この反応は、水中または均一なもしくは水/酢酸エチル混合物のような不均一な水/有機媒体中で実施される。
の得られるラクタムの窒素原子の保護によっても得られることができる。
ニル基を表す、一般式(V)の生成物は、一般式(VIII)の生成物とのアルキルアミンの反応、その後の[脱落]水素原子による保護基G2の置換により、ならびに場合によっては水素原子によるR'1およびR"1の基の置換により得られることができる。
11cm3の水中の4.12gのN-メチルモルホリンオキシド、およびその後、ゆっくりと、360μlのtert-ブタノール中四酸化オスミウム(OsO4)の2.5%(w/v)溶液を、還流冷却器および攪拌システムを装備され、70cm3のtert-ブタノール中の7gの2-(α-S-メチルベンジル)-2-アザビシクロ[2.2.1]ヘプト-5-エン(35mmol)の溶液を含有する250cm3の三ツ口丸底フラスコに、およそ25℃の温度で添加する。この混合物を、およそ20℃の温度で1時間、そしてその後65℃で4時間攪拌する。減圧下にtert-ブタノールを蒸発させた後、残渣を150cm3のイソプロパノールに溶解する。減圧下に乾固まで濃縮した後、8.27gの生成物を得、そのプロトンNMRスペクトルは、それが5R,6S-ジヒドロキシ-2-(α-S-メチルベンジル)-2-アザビシクロ[2.2.1]ヘプタンおよび5S,6R-ジヒドロキシ-2-(α-S-メチルベンジル)-2-アザビシクロ[2.2.1]ヘプタンの混合物(モル数で78/22)から成ることを示す。
Claims (2)
- 一般式(V):
で表される化合物の製造方法であって、得ることが所望されるR2基の性質に依存して、無機塩基、アルカリ金属アルコキシド、アルキルアミンまたはアルカリ金属ホウ化水素と、一般式(VIII):
で表される化合物を反応させ、次いで、R'1およびR"1の基ならびに基G2が水素原子により置換されてもよいことを特徴とする、上記方法。 - 一般式(V):
で表される化合物の製造方法であって、
一般式(VIII):
で表される化合物の基G2を水素により置換し、こうして得られる化合物を、次いで、得ることを所望するR2の基の性質に依存して、無機塩基、アルカリ金属アルコキシド、アルキルアミンまたはアルカリ金属ホウ化水素と反応させ、その後、R'1およびR"1の基が水素原子により置換されてもよいことを特徴とする、上記方法。
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9506353A FR2734822B1 (fr) | 1995-05-30 | 1995-05-30 | Nouveaux derives du 2-azabicyclo(2.2.1)heptane, leur preparation et leur application |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP53624696A Division JP4097287B2 (ja) | 1995-05-30 | 1996-05-28 | 2−アザビシクロ[2.2.1]ヘプタン誘導体、それらの調製法およびそれらの用途 |
Publications (1)
Publication Number | Publication Date |
---|---|
JP2007262089A true JP2007262089A (ja) | 2007-10-11 |
Family
ID=9479463
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP53624696A Expired - Fee Related JP4097287B2 (ja) | 1995-05-30 | 1996-05-28 | 2−アザビシクロ[2.2.1]ヘプタン誘導体、それらの調製法およびそれらの用途 |
JP2007179423A Pending JP2007262089A (ja) | 1995-05-30 | 2007-07-09 | アミノ置換カルボ糖の製造方法 |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP53624696A Expired - Fee Related JP4097287B2 (ja) | 1995-05-30 | 1996-05-28 | 2−アザビシクロ[2.2.1]ヘプタン誘導体、それらの調製法およびそれらの用途 |
Country Status (25)
Country | Link |
---|---|
EP (1) | EP0828740B1 (ja) |
JP (2) | JP4097287B2 (ja) |
KR (1) | KR100488393B1 (ja) |
CN (1) | CN1249034C (ja) |
AP (1) | AP973A (ja) |
AT (1) | ATE205210T1 (ja) |
AU (1) | AU711057B2 (ja) |
BG (1) | BG63084B1 (ja) |
BR (1) | BR9608513A (ja) |
CA (1) | CA2219456A1 (ja) |
CZ (1) | CZ286483B6 (ja) |
DE (1) | DE69615020T2 (ja) |
DK (1) | DK0828740T3 (ja) |
EA (1) | EA000963B1 (ja) |
ES (1) | ES2163023T3 (ja) |
GR (1) | GR3036536T3 (ja) |
HU (1) | HUP9900787A3 (ja) |
NO (1) | NO311431B1 (ja) |
OA (1) | OA10543A (ja) |
PL (1) | PL186195B1 (ja) |
PT (1) | PT828740E (ja) |
RO (1) | RO119414B1 (ja) |
SI (1) | SI0828740T1 (ja) |
SK (1) | SK283809B6 (ja) |
UA (1) | UA64695C2 (ja) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0719719A (ja) * | 1993-07-05 | 1995-01-20 | Matsushita Electric Ind Co Ltd | 断熱箱体 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4803272A (en) * | 1987-02-24 | 1989-02-07 | E. I. Du Pont De Nemours And Company | S-modified adenosyl-1,8-diamino-3-thiooctane derivatives |
US4954504A (en) * | 1986-11-14 | 1990-09-04 | Ciba-Geigy Corporation | N9 -cyclopentyl-substituted adenine derivatives having adenosine-2 receptor stimulating activity |
US5063233A (en) * | 1986-11-14 | 1991-11-05 | Ciba-Geigy Corporation | N9 -cyclopentyl-substituted adenine derivatives useful as adenosine receptor agonists |
WO1994017090A1 (en) * | 1993-01-20 | 1994-08-04 | Glaxo Group Limited | 2,6-diaminopurine derivatives |
WO1995028160A1 (en) * | 1994-04-19 | 1995-10-26 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Compounds having antihypertensive, cardioprotective, anti-ischemic and antilipolytic properties |
-
1996
- 1996-05-28 AU AU60087/96A patent/AU711057B2/en not_active Ceased
- 1996-05-28 HU HU9900787A patent/HUP9900787A3/hu unknown
- 1996-05-28 SI SI9630340T patent/SI0828740T1/xx unknown
- 1996-05-28 AT AT96917555T patent/ATE205210T1/de active
- 1996-05-28 UA UA97115616A patent/UA64695C2/uk unknown
- 1996-05-28 PT PT96917555T patent/PT828740E/pt unknown
- 1996-05-28 DE DE69615020T patent/DE69615020T2/de not_active Expired - Lifetime
- 1996-05-28 JP JP53624696A patent/JP4097287B2/ja not_active Expired - Fee Related
- 1996-05-28 PL PL96323680A patent/PL186195B1/pl not_active IP Right Cessation
- 1996-05-28 ES ES96917555T patent/ES2163023T3/es not_active Expired - Lifetime
- 1996-05-28 EP EP96917555A patent/EP0828740B1/fr not_active Expired - Lifetime
- 1996-05-28 SK SK1612-97A patent/SK283809B6/sk not_active IP Right Cessation
- 1996-05-28 CZ CZ19973777A patent/CZ286483B6/cs not_active IP Right Cessation
- 1996-05-28 BR BR9608513A patent/BR9608513A/pt not_active IP Right Cessation
- 1996-05-28 CA CA002219456A patent/CA2219456A1/fr not_active Abandoned
- 1996-05-28 AP APAP/P/1997/001149A patent/AP973A/en active
- 1996-05-28 KR KR1019970708582A patent/KR100488393B1/ko not_active IP Right Cessation
- 1996-05-28 RO RO97-02201A patent/RO119414B1/ro unknown
- 1996-05-28 EA EA199700440A patent/EA000963B1/ru not_active IP Right Cessation
- 1996-05-28 DK DK96917555T patent/DK0828740T3/da active
-
1997
- 1997-11-28 OA OA70143A patent/OA10543A/fr unknown
- 1997-11-28 NO NO19975487A patent/NO311431B1/no not_active IP Right Cessation
- 1997-11-28 BG BG102081A patent/BG63084B1/bg unknown
-
2001
- 2001-09-06 GR GR20010400676T patent/GR3036536T3/el unknown
-
2002
- 2002-02-20 CN CNB021046816A patent/CN1249034C/zh not_active Expired - Fee Related
-
2007
- 2007-07-09 JP JP2007179423A patent/JP2007262089A/ja active Pending
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4954504A (en) * | 1986-11-14 | 1990-09-04 | Ciba-Geigy Corporation | N9 -cyclopentyl-substituted adenine derivatives having adenosine-2 receptor stimulating activity |
US5063233A (en) * | 1986-11-14 | 1991-11-05 | Ciba-Geigy Corporation | N9 -cyclopentyl-substituted adenine derivatives useful as adenosine receptor agonists |
US4803272A (en) * | 1987-02-24 | 1989-02-07 | E. I. Du Pont De Nemours And Company | S-modified adenosyl-1,8-diamino-3-thiooctane derivatives |
WO1994017090A1 (en) * | 1993-01-20 | 1994-08-04 | Glaxo Group Limited | 2,6-diaminopurine derivatives |
WO1995028160A1 (en) * | 1994-04-19 | 1995-10-26 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Compounds having antihypertensive, cardioprotective, anti-ischemic and antilipolytic properties |
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