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

[41] FORMAL SYNTHESIS OF (5R,8R,8aS)-INDOLIZIDINE 209I VIA ENAMINONES INCORPORATING WEINREB AMIDES
de Koning, Charles B.
Michael, Joseph P.
Riley, Darren L.
HETEROCYCLES, 2009, 79 : 935 - 953
[42] The efficient synthesis of (3R,4R,5R)-3-amino-4,5-dimethyl-octanoic acid, a chiral β-amino acid with potent affinity for the α2δ protein
Zhang, Ji
Blazecka, Peter G.
Pflum, Derek A.
Bozelak, Joseph
Vrieze, Derek
Colbry, Norman L.
Hoge, Garrett
Boyles, David C.
Samas, Brian
Curran, Timothy T.
Osuma, Augustine T.
Johnson, Paul
Kesten, Suzanne
Schwarz, Jacob B.
Goodman, Annise
Plummer, Mark
Akin, Anne
Huang, Yun
Lovdahl, Michael
Thorpe, Andrew J.
TETRAHEDRON LETTERS, 2009, 50 (11) : 1167 - 1170
[43] Asymmetric synthesis and receptor pharmacology of the group II mGlu receptor ligand (1S,2R,3R,5R,6S)-2-amino3-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylic Acid -: HYDIA
Woltering, Thomas J.
Adam, Geo
Huguenin, Philipp
Wichmann, Juergen
Kolczewski, Sabine
Gatti, Silvia
Bourson, Anne
Kew, James N. C.
Richards, Grayson
Kemp, John A.
Mutel, Vincent
Knoflach, Frederic
CHEMMEDCHEM, 2008, 3 (02) : 323 - 335
[44] (2R,1′S,2′R)- and (2S,1′S,2′R)-3-[2-Mono(di,tri)fluoromethylcyclopropyl]alanines and their incorporation into hormaomycin analogues
de Meijere, Armin
Kozhushkov, Sergei I.
Yufit, Dmitrii S.
Grosse, Christian
Kaiser, Marcel
Raev, Vitaly A.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2014, 10 : 2844 - 2857
[45] Concise Stereoselective Synthesis of β-Hydroxy-γ-lactones: (4R,5R)-4-Hydroxy-γ-decalactone from the Japanese Orange Fly and Enantiomers of Arachnid Harvestmen Isolates
Gangani, Ashvin J.
Kumar, Praveen
Fernandes, Rodney A.
JOURNAL OF NATURAL PRODUCTS, 2021, 84 (01): : 120 - 125
[46] An efficient synthesis of an optically active (-)-(3R, 4R, 5R)-4-(1-hydroxylisopropyl)-3-acetyloxyl-butyrolactone
Wang, JX
Zhang, CX
Li, Y
You, QD
JOURNAL OF CHEMICAL RESEARCH-S, 2005, (10): : 665 - 668
[47] Development of a Scalable Synthetic Route to (1R,5R)-2,2-Dimethoxybicyclo[3.1.0]hexan-3-one: An Important Intermediate in the Synthesis of Lenacapavir
De Souza, Aline Nunes
Sakkani, Nagaraju
Guthrie, Daryl
Sahani, Rajkumar Lalji
Saathoff, John M.
Hochstetler, Samuel R.
Burns, Justina M.
Ahmad, Saeed
Laidlaw, G. Michael
Gupton, B. Frank
Klumpp, Douglas A.
Jin, Limei
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2025, 29 (03) : 846 - 855
[48] Total synthesis of (5R,6R,8R,9S)-(-)-5,9Z-indolizidine 221T using sulfinimine-derived N-sulfinyl β-amino ketones
Davis, Franklin A.
Song, Minsoo
Qiu, Hui
Chai, Jing
ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (24) : 5067 - 5073
[49] Chiron approach towards the synthesis of (2S,3R)-3-hydroxyornithine, (2S,3R)-3-hydroxylysine and tetrahydroazepine core of (-)-balanol
Rohokale, Rajendra
Dhavale, Dilip
TETRAHEDRON, 2016, 72 (30) : 4550 - 4555
[50] (5R,7R)-5-Methylheptadecan-7-ol: a novel sex pheromone component produced by a female lichen moth, Miltochrista calamina, in the family Arctiidae
Yamakawa, Rei
Kiyota, Ryutaro
Taguri, Tomonori
Ando, Tetsu
TETRAHEDRON LETTERS, 2011, 52 (44) : 5808 - 5811

← 1 2 3 4 5 →