15366-19-5

Upstream product

• 186581-53-3 diazomethane 
• 5672-83-3 Z-L-GluOMe 
• 67-56-1 methanol 
• 58456-27-2 (S)-3-(benzyloxycarbonyl)-4-(4-diazo-3-oxobutyl)-5-oxazolidinone 
• 1155-62-0 N-benzyloxycarbonyl-L-glutamic acid 
• 23632-67-9 (S)-3-[3-(benzyloxycarbonyl)-5-oxooxazolidin-4-yl]propanoic acid 
• 13907-82-9 N²-benzyloxycarbonyl-L-glutamine methyl ester 
• 5672-82-2 N-Z-L-Glu-OMe-4g-Dcha salt 
• 117836-15-4 (S)-2-Benzyloxycarbonylamino-5-ethoxycarbonyloxy-5-oxo-pentanoic acid methyl ester 

Downstream Products

• 15366-20-8 (S)-dimethyl 2-(benzyloxycarbonylamino)hexanedioate 
• 1118-90-7 L-homoglutamic acid 
• 65427-31-8 (S)-2-Benzyloxycarbonylamino-6-chloro-5-oxo-hexanoic acid methyl ester 
• 117836-13-2 (S)-5-Oxo-piperidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester 
• 309928-91-4 methyl (2S)-2-benzyloxycarbonylamino-6-bromo-5-oxohexanoate 
• 18899-29-1 (2S,5S)-5-hydroxylysine 
• 504-91-6 (5R)-5-hydroxy-L-lysine 
• 309928-95-8 (2S,5S)-5-azidomethyl-2-benzyloxycarbonylamino-δ-valerolactone 
• 309928-94-7 (2S,5R)-5-azidomethyl-2-benzyloxycarbonylamino-δ-valerolactone 
• 309928-92-5 methyl (S)-6-azido-2-benzyloxycarbonylamino-5-oxohexanoate 
• 309928-97-0 (2S,5S)-6-azido-2-benzyloxycarbonylamino-5-hydroxyhexanoic acid 
• 309928-96-9 (2S,5R)-6-azido-2-benzyloxycarbonylamino-5-hydroxyhexanoic acid 
• 917507-80-3 (2S,5S)-N-[(benzyloxy)carbonyl]-5-hydroxy-2-piperidinecarboxylic acid 
• 117836-26-7 cis-5(S)-hydroxy-2(S)-N₁-benzyloxycarbonylpipecolic acid methyl ester 

Relevant academic research and scientific papers

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.

Cleavage of benzyloxycarbonyl-5-oxazolidinones to α-benzyloxycarbonylamino-α-alkyl esters by alcohols and sodium hydrogen carbonate

The reaction of benzyloxycarbonyl-5-oxazolidinones with alcohols and sodium hydrogen carbonate to afford the corresponding benzyloxycarbonyl esters is described.

Synthesis of all four possible stereoisomers of 5-hydroxylysine

A simple protocol for the transformation of L- and D-glutamic acids into the enantiopure forms of all four isomers of 5-hydroxylysine is described. Copyright (C) 2000 Elsevier Science Ltd.

Synthesis of 5-oxo-L-pipecolic acid derivatives by rhodium(II) acetate catalyzed cyclization of diazoketones

A convenient synthesis of 5-oxo-L-pipecolic acid derivatives is described. The key step involves the rhodium(II) acetate catalysed N-H insertion reaction of diazoketones, which are derived from L-glutamic acid.

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.

Synthesis of amino acids diazoketones

A study of carboxylic acid -> diazoketone conversion was pursued employing the γ-carboxyl group of otherwise protected L-glutamic acids.The Arndt-Eistert route employing carboxylic acid chloride intermediates was found best (52percent yield,5b), performed