An efficient and scalable synthesis of N-(benzyloxycarbonyl)- and N-(methyloxycarbonyl)-(S)-vinylglycinol

被引：14

作者：

Lumbroso, Alexandre ^{[1
]}

Coeffard, Vincent ^{[1
]}

Le Grognec, Erwan ^{[1
]}

Beaudet, Isabelle ^{[1
]}

Quintard, Jean-Paul ^{[1
]}

机构：

[1] Univ Nantes, CNRS, UMR 6230, Fac Sci & Tech, F-44322 Nantes 3, France

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 24期

关键词：

Chiral beta-amino alcohol; Vinylglycine; Amino acid; Preparative procedure; ALPHA-AMINO-ACIDS; CONVENIENT SYNTHESIS; ASYMMETRIC-SYNTHESIS; CHIRAL AUXILIARIES; 1,2-AMINO ALCOHOLS; VINYLGLYCINE; DERIVATIVES; (R)-PHENYLGLYCINOL; TRANSMETALATION; PRECURSORS;

D O I：

10.1016/j.tetlet.2010.04.059

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and scalable synthesis of N-(benzyloxycarbonyl)- and N-(methyloxycarbonyl)-(S)-vinylglycinol has been reported starting from the commercially available (L)-methionine. The scale-up preparation consisted of 5 steps and delivered up to 50 g of the desired N-protected beta-amino alcohols in 32% and 36% overall yields. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：3226 / 3228

页数：3

共 50 条

[1] Methyl N-(benzyloxycarbonyl)oxamate
Marx, R
Glaser, SJ
Bolte, M
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2003, 59 : O1425 - O1426
[2] RESOLUTION AND DEBLOCKING OF RACEMIC N-(BENZYLOXYCARBONYL)CYCLOPROPYLPHENYLALANINE
KIMURA, H
STAMMER, CH
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (14): : 2440 - 2441
[3] Catalysis in the Synthesis of S,N-Heterocycles and O,N-, S,N-, and O,S,N-Macroheterocycles
Rakhimova, E. B.
Ozden, I. V.
Ibragimov, A. G.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 54 (07) : 961 - 986
[4] Synthesis of N-(Benzyloxyethyl)- and N-(Alkoxycarbonylmethyl)nitrones
Diez-Martinez, Alba
Gultekin, Zeynep
Delso, Ignacio
Tejero, Tomas
Merino, Pedro
SYNTHESIS-STUTTGART, 2010, (04): : 678 - 688
[5] RACEMIZATION OF N-(BENZYLOXYCARBONYL)-S-BENZYLCYSTEINE SUBSTITUTED PHENYL ESTERS
MARTYNOV, VF
SAMARTSE.MA
JOURNAL OF GENERAL CHEMISTRY USSR, 1969, 39 (04): : 911 - &
[6] Catalysis in the Synthesis of S,N-Heterocycles and O,N-, S,N-, and O,S,N-Macroheterocycles
E. B. Rakhimova
I. V. Ozden
A. G. Ibragimov
Russian Journal of Organic Chemistry, 2018, 54 : 961 - 986
[7] Synthesis and crystal structure of enantiomeric N-(dimethylfluorosilylmethyl) and N-(dimethylchlorosilylmethyl)-[N-(S)-1-phenylethyl)] acetamides
Baukov, YI
Ovchinnikov, YE
Shipov, AG
Kramarova, EP
Negrebetsky, VV
Struchkov, YT
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1997, 536 (1-2) : 399 - 403
[8] SYNTHESIS AND HERBICIDAL PROPERTIES OF N-(BENZYLIDENEAMINO),N-(BENZYLAMINO), AND N-(PHENYLAZO) HETEROCYCLES
PILGRAM, KH
KOLLMEYER, WD
SKILES, RD
WITTSELL, LE
ACS SYMPOSIUM SERIES, 1987, 355 : 36 - 53
[9] N-(benzyloxycarbonyl)glycine esters and amides as new anticonvulsants
Geurts, M
Poupaert, JH
Scriba, GKE
Lambert, DM
JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (01) : 24 - 30
[10] New possibilities of the Mannich reaction in the synthesis of N-, S,N-, and Se,N-heterocycles
V. V. Dotsenko
K. A. Frolov
E. A. Chigorina
A. N. Khrustaleva
E. Yu. Bibik
S. G. Krivokolysko
Russian Chemical Bulletin, 2019, 68 : 691 - 707

← 1 2 3 4 5 →