JPS57112369A - Intermediate of mugineic acids and its preparation - Google Patents
Intermediate of mugineic acids and its preparationInfo
- Publication number
- JPS57112369A JPS57112369A JP55185539A JP18553980A JPS57112369A JP S57112369 A JPS57112369 A JP S57112369A JP 55185539 A JP55185539 A JP 55185539A JP 18553980 A JP18553980 A JP 18553980A JP S57112369 A JPS57112369 A JP S57112369A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- group
- acid
- imino
- mugineic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000002253 acid Substances 0.000 title abstract 3
- 150000007513 acids Chemical class 0.000 title abstract 2
- -1 γ-aminobutyric acid ester Chemical class 0.000 abstract 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- OGNSCSPNOLGXSM-UHFFFAOYSA-N (+/-)-DABA Natural products NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 abstract 2
- 229960003692 gamma aminobutyric acid Drugs 0.000 abstract 2
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutanoic acid Natural products NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 abstract 2
- CUZKLRTTYZOCSD-UHFFFAOYSA-N (-)-2'-deoxymugineic acid Natural products OC(=O)C(O)CCNC(C(O)=O)CCN1CCC1C(O)=O CUZKLRTTYZOCSD-UHFFFAOYSA-N 0.000 abstract 1
- CUZKLRTTYZOCSD-CIUDSAMLSA-N 2'-deoxymugineic acid Chemical compound OC(=O)[C@@H](O)CCN[C@H](C(O)=O)CCN1CC[C@H]1C(O)=O CUZKLRTTYZOCSD-CIUDSAMLSA-N 0.000 abstract 1
- QUKMQOBHQMWLLR-MGURRDGZSA-N 4-[[(1S)-1-carboxy-3-hydroxypropyl]amino]-2-[(3-carboxy-3-hydroxypropyl)amino]butanoic acid Chemical compound OCC[C@H](NCCC(NCCC(O)C(O)=O)C(O)=O)C(O)=O QUKMQOBHQMWLLR-MGURRDGZSA-N 0.000 abstract 1
- 229930195135 Avenic acid Natural products 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 230000008878 coupling Effects 0.000 abstract 1
- 238000010168 coupling process Methods 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000001841 imino group Chemical group [H]N=* 0.000 abstract 1
- GJRGEVKCJPPZIT-UHFFFAOYSA-N isomugineic acid Natural products OC(=O)C(O)CCNC(C(O)=O)C(O)CN1CCC1C(O)=O GJRGEVKCJPPZIT-UHFFFAOYSA-N 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- GJRGEVKCJPPZIT-JBDRJPRFSA-N mugineic acid Chemical compound OC(=O)[C@@H](O)CCN[C@H](C(O)=O)[C@@H](O)CN1CC[C@H]1C(O)=O GJRGEVKCJPPZIT-JBDRJPRFSA-N 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 238000006268 reductive amination reaction Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 abstract 1
Classifications
-
- 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
- Furan Compounds (AREA)
- Pyrane Compounds (AREA)
Abstract
NEW MATERIAL:The γ-aminobutyric acid ester derivative of formulaI[n is 0W3; R1WR5 are H or OH group protected with tetrahydropyranyl group, etc.; A is group of formula II (R is H or tetrahydropyranoxy), formula III, formula IV, etc. bonded through the nitrogen atom of amino or imino group; B is imino- protecting group such as t-butoxycarbonyl group].
EXAMPLE: α-Tetrahydropyranoxy-γ-tetrahydrofuranoaminobutyric acid benzyl ester.
USE: Intermediate for the synthesis of mugineic acids such as mugineic acid, 2'- deoxymugineic acid, avenic acid, etc.
PROCESS: The γ-aminobutyric acid ester of formulaIIis prepared by the reductive amination of the aldehyde of formula V with the amino compound or imino compound of formula VI, formula VII, formula VIII, etc. or their salts in a solvent such as methanol using a reducing agent such as sodium cyanoborohydride, followed by coupling of the reaction product.
COPYRIGHT: (C)1982,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55185539A JPS57112369A (en) | 1980-12-29 | 1980-12-29 | Intermediate of mugineic acids and its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55185539A JPS57112369A (en) | 1980-12-29 | 1980-12-29 | Intermediate of mugineic acids and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57112369A true JPS57112369A (en) | 1982-07-13 |
| JPH0120148B2 JPH0120148B2 (en) | 1989-04-14 |
Family
ID=16172570
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP55185539A Granted JPS57112369A (en) | 1980-12-29 | 1980-12-29 | Intermediate of mugineic acids and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57112369A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6682806B1 (en) | 1999-02-19 | 2004-01-27 | Ronald H. Ball | Method of applying a protective film, optionally including advertising or other visible material, to the surface of a handrail for an escalator or moving walkway |
| US7108905B2 (en) | 2000-02-22 | 2006-09-19 | Ronald H. Ball | Protective film for the surface of a handrail for an escalator or moving walkway |
| US7278528B2 (en) | 1999-02-19 | 2007-10-09 | Ronald H. Ball | Method of and apparatus for applying a film optionally including advertising or other visible material, to the surface of a handrail for an escalator or moving walkway |
-
1980
- 1980-12-29 JP JP55185539A patent/JPS57112369A/en active Granted
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6682806B1 (en) | 1999-02-19 | 2004-01-27 | Ronald H. Ball | Method of applying a protective film, optionally including advertising or other visible material, to the surface of a handrail for an escalator or moving walkway |
| US7041195B2 (en) | 1999-02-19 | 2006-05-09 | Ronald H. Ball | Method of applying and removing a protective film to the surface of a handrail for an escalator or moving walkway |
| US7278528B2 (en) | 1999-02-19 | 2007-10-09 | Ronald H. Ball | Method of and apparatus for applying a film optionally including advertising or other visible material, to the surface of a handrail for an escalator or moving walkway |
| US7951254B2 (en) | 1999-02-19 | 2011-05-31 | Ehc Canada, Inc. | Method of applying advertising to the surface of a moving handrail |
| US7108905B2 (en) | 2000-02-22 | 2006-09-19 | Ronald H. Ball | Protective film for the surface of a handrail for an escalator or moving walkway |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0120148B2 (en) | 1989-04-14 |
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