JPS56110671A - Preparation of thienamycin intermediate - Google Patents
Preparation of thienamycin intermediateInfo
- Publication number
- JPS56110671A JPS56110671A JP1324880A JP1324880A JPS56110671A JP S56110671 A JPS56110671 A JP S56110671A JP 1324880 A JP1324880 A JP 1324880A JP 1324880 A JP1324880 A JP 1324880A JP S56110671 A JPS56110671 A JP S56110671A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- ring
- groups
- thienamycin
- 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.)
- Pending
Links
Abstract
PURPOSE: To prepare an intermediate for the selective synthesis of a natural fermentation type thienamycin, in high yield, by converting the OH or OH and NH2 of an easily preparable specific amino ester compound used as starting material to trialkyl silyl groups, subjecting the compound to ring-closing reaction, and eliminating the trialkylsilyl groups.
CONSTITUTION: A compound of formula VI (R1 and R2 are alkyl) is used as a raw material, and reacted with trialkyl halogenosilane to convert the OH or the OH and the NH2 groups to trialkylsilyl groups. The product is subjected to ring-closing by Gringnard reaction to obtain the compound of formula IX. Elimination of the trialkylsilyl groups gives the thienamycin intermediate of formula II. The compound of formula VI can be prepared by (1) reacting the simple compound of formula III with the compound of formula IV to afford a novel isoxazoline of formula V, and (2) reducing the compound with sodium borohydride, etc. in the presence of nickel chloride, etc. The reduction after the silylation affords the ring-closing reaction keeping the original steric configuration in high yield and low isomer production.
COPYRIGHT: (C)1981,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1324880A JPS56110671A (en) | 1980-02-06 | 1980-02-06 | Preparation of thienamycin intermediate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1324880A JPS56110671A (en) | 1980-02-06 | 1980-02-06 | Preparation of thienamycin intermediate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS56110671A true JPS56110671A (en) | 1981-09-01 |
Family
ID=11827898
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1324880A Pending JPS56110671A (en) | 1980-02-06 | 1980-02-06 | Preparation of thienamycin intermediate |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS56110671A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007281417A (en) * | 2006-04-04 | 2007-10-25 | Lg Phillips Lcd Co Ltd | Light-emitting diode driving device and liquid crystal display using the same |
-
1980
- 1980-02-06 JP JP1324880A patent/JPS56110671A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007281417A (en) * | 2006-04-04 | 2007-10-25 | Lg Phillips Lcd Co Ltd | Light-emitting diode driving device and liquid crystal display using the same |
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