Stereoselective synthesis of (2R,5R)- and (2S,5R)-5-hydroxylysine

被引：0

作者：

van den Nieuwendijk, AMCH ^{[1
]}

Kriek, NMAJ ^{[1
]}

Brussee, J ^{[1
]}

van Boom, JH ^{[1
]}

van der Gen, A ^{[1
]}

机构：

[1] Leiden Univ, Leiden Inst Chem, Gorlaeus Labs, NL-2300 RA Leiden, Netherlands

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2000年 / 2000卷 / 22期

关键词：

asymmetric synthesis; natural products; cyanohydrins; template synthesis; amino acids;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereoselective synthesis of (2S,5R)-5-hydroxylysine (1) and (2R,5R)-5-hydroxylysine (17), based on a concept involving Williams glycine template methodology and (R)-hydroxynitrile lyase for the introduction of chirality at the alpha -position and the side-chain, respectively, is described. This strategy offers an expeditious route towards orthogonally protected 5-hydroxylysines.

引用

页码：3683 / 3691

页数：9

共 50 条

[1] Practical synthesis of (2R,5R)-2,5-hexanediol
Saravanan, P
Raina, S
Sambamurthy, T
Singh, VK
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (08) : 2669 - 2670
[2] (1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl (R)-4-methylbenzenesulfonimidate
Tota, Arianna
Andresini, Michael
Colella, Marco
Dibenedetto, Roberta Savina
Degennaro, Leonardo
Luisi, Renzo
MOLBANK, 2022, 2022 (04)
[3] Synthesis of (R)-Lactic Acid and (2R, 5R)-2-tert-Butyl-5-methyl-1,3-dioxolan-4-one
Aitken, R. Alan
Meehan, Anna
Power, Lynn A.
SYNTHESIS-STUTTGART, 2015, 47 (11): : 1557 - 1559
[4] Diastereoselective syntheses of (2R,3R,5R)- and (2S,3S,5S)-3-hydroxy-5-methyl-2-pyrrolidinecarboxylic acid as a component of actinomycin Z1
Tanaka, K
Sawanishi, H
TETRAHEDRON, 1998, 54 (34) : 10029 - 10042
[5] New insights into the classic chiral Grignard reagent (1R,2S,5R)-menthylmagnesium chloride
Beckmann, Jens
Dakternieks, Dainis
Draeger, Martin
Duthie, Andrew
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (39) : 6509 - 6512
[6] A concise synthesis of (4R,5R)-(-)-muricatacin and (4R,5R)-L-(-)-factor from D-glucono-δ-lactone
Chaudhari, Dipali A.
Ingle, Arun B.
Fernandes, Rodney A.
TETRAHEDRON-ASYMMETRY, 2016, 27 (2-3) : 114 - 117
[7] Multienzymatic cascade synthesis of an enantiopure (2R,5R)-1,3-oxathiolane anti-HIV agent precursor
Ren, Yansong
Hu, Lei
Ramstrom, Olof
MOLECULAR CATALYSIS, 2019, 468 : 52 - 56
[8] Syntheses of (4R, 5S)- and (4S, 5R)-Muricatacins, and (4S, 5R)-aza-muricatacin, unnatural analogues of the Annonaceous acetogenin
Konno, H
Hiura, N
Yanaru, M
HETEROCYCLES, 2002, 57 (10) : 1793 - 1797
[9] Synthesis and stereochemistry assignment of (3R,5R)- and (3S,5R)-4-benzyl-3-(3,4-dimethoxyphenyl)-5-phenyl-1,4-oxazin-2-ones
Grajewska, Agnieszka
Rozwadowska, Maria D.
Gzella, Andrzej
JOURNAL OF MOLECULAR STRUCTURE, 2019, 1194 : 204 - 210
[10] Asymmetric synthesis of palitantin from the (5R)-tert-butyldimethylsiloxy-2-cyclohexenone
Hareau, G
Koiwa, M
Hanazawa, T
Sato, F
TETRAHEDRON LETTERS, 1999, 40 (42) : 7493 - 7496

← 1 2 3 4 5 →