917507-80-3

Upstream product

• 169825-97-2 N-benzyloxycarbonyl-(2S,5S)-5-hydroxypipecolic acid tert-butyl ester 
• 65427-31-8 (S)-2-Benzyloxycarbonylamino-6-chloro-5-oxo-hexanoic acid methyl ester 
• 23632-67-9 (S)-3-[3-(benzyloxycarbonyl)-5-oxooxazolidin-4-yl]propanoic acid 
• 117836-16-5 (S)-2-Benzyloxycarbonylamino-6-chloro-5-hydroxy-hexanoic acid methyl ester 
• 121895-18-9 (S)-2-amino-6-hydroxyhexanoic acid methyl ester hydrochloride 
• 44601-24-3 4-hydroxypentanal 
• 110-87-2 3,4-dihydro-2H-pyran 
• 117836-27-8 (2S,5R)-5-Hydroxy-piperidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester 
• 824943-45-5 (2S,5R)-5-hydroxy-6-methoxy-piperidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester 
• 227758-97-6 (2S)-3,4-dihydro-2H-pyridine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester 
• 154061-64-0 (2S)-2-<(Benzyloxycarbonyl)amino>-6-hydroxyhexanoic acid methyl ester 
• 117894-79-8 benzyl (1S,4S)-5-aza-2-oxa-3-oxobicyclo[2.2.2]octane-5-carboxylate 
• 501-53-1 benzyl chloroformate 
• 448964-01-0 (2S)-5-hydroxy-2-piperidinecarboxylic acid 

Downstream Products

• 63088-78-8 (2S,5R)-5-hydroxypiperidine-2-carboxylic acid 

Relevant academic research and scientific papers

MANUFACTURING METHOD OF (2S,5S)-5-HYDROXY-2-PIPERIDINECARBOXYLIC ACID AS WELL AS MANUFACTURING INTERMEDIATE OF THE SAME AND METHOD FOR MANUFACTURING THE SAME

PROBLEM TO BE SOLVED: To provide synthesis methods of 5-hydroxy-6-methoxypiperidine-2-carboxylic acid derivatives and 5-oxopiperidine-2-carboxylic acid derivatives more safely than ever by using inexpensive raw ingredients. SOLUTION: In the provided method, a compound expressed by the following formula [X] is manufactured from a compound expressed by the following formula [I] through steps (1) through (9) [either steps (4) and (5) or steps (6) and (7) in the case of steps (4) through (7)]. COPYRIGHT: (C)2015,JPOandINPIT

METHOD FOR PRODUCING cis-5-HYDROXY-2-PIPERIDINECARBOXYLIC ACID DERIVATIVE, AND METHOD FOR PURIFYING cis-5-HYDROXY-2-PIPERIDINECARBOXYLIC ACID

The present invention aims to provide a method for purifying cis-5-hydroxy-2-piperidinecarboxylic acid with high purity, and a method for producing its derivative. The present invention provides a method for producing a cis-5-hydroxy-2-piperidinecarboxylic acid derivative, which method comprises a step of converting cis-5-hydroxy-2-piperidinecarboxylic acid into a compound(s) of Formula (1) and/or Formula (2) (wherein R1 represents a protective group for an amino group, and R2 represents a C1-C6 alkyl group), and a method for purifying cis-5-hydroxy-2-piperidinecarboxylic acid.

Diastereoselective synthesis of (2S,5S)- and (2S,5R)-N-benzyloxycarbonyl-5-hydroxypipecolic acids from trans-4-hydroxy-l-proline

An efficient diastereoselective synthesis of cis- and trans-5-hydroxy-(2S)-N-benzyloxycarbonyl pipecolic acids, starting from trans-4-hydroxy-l-proline is described. The key synthetic strategies involve the regioisomeric ring expansion of keto ester 8 and diastereoselective reduction of ketone 11 in high selectivity and yield.

An efficient route to the α-methyl ester of L-glutamic acid, and its conversion into cis-5-hydroxy-L-pipecolic acid

The treatment of the N-benzyloxycarbonyl α-methyl esters of L-glutamine or L-asparagine with tert-butyl nitrite in refluxing acetonitrile results in selective hydrolysis of the amide group, giving optically pure Z-Glu-OMe (74%) or Z-Asp-OMe (88%); these are versatile chiral building blocks, and an efficient synthesis of cis-5-hydroxy-L-pipecolic acid from Z-Glu-OMe is described.

CHIRAL SYNTHESIS OF 5-HYDROXY-(L)-PIPECOLIC ACIDS FROM (L)-GLUTAMIC ACID

A stereo- and enantio-specific synthesis of the naturally occuring cis-5-hydroxy-(L)-pipecolic acid (3) is described, starting from Z-(L)-glutamic acid; the key step involves cyclisation of a protected chlorohydrin, and also gives access to trans-5-hydroxy-(L)-pipecolic acid.