A concise synthesis of (3S,4S,5R)-1-(α-D-galactopyranosyl)-3-tetracosanoylamino-4,5-decanediol, a C-glycoside analogue of immunomodulating α-galactosylceramide OCH

被引：28

作者：

Toba, T

Murata, K

Yamamura, T

Miyake, S

Annoura, H

机构：

[1] Daiichi Suntory Pharma Co Ltd, Biomed Res Labs, Osaka 6188513, Japan

[2] Natl Inst Neurosci, NCNP, Dept Immunol, Tokyo 1878502, Japan

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 30期

关键词：

C-glycoside; OCH; ceramide; CD1d; NKT cell ligand;

D O I：

10.1016/j.tetlet.2005.05.069

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise and convergent synthesis of the C-glycoside analogue 2b of immunomodulating alpha-galactosylceramide OCH 1b starting from readily available 2,3,4,6-tetra-O-bensyl-D-galactose 3 and L-arabinose 6 is described. The synthesis features the nucleophilic addition of an alpha-ethynyl sugar 5 to the phytosphingosine-precursor aldehyde 9 and would be applicable to a variety of C-glycoside analogues of interest. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：5043 / 5047

页数：5

共 50 条

[21] Catalytic Route to a Concise Stereoselective Synthesis of Cytotoxic (3S,5S)-1-(4-Hydroxyphenyl)-7-phenylheptane-3,5-diol and Its (3R,5S)-Isomer
Reddy, S. Purushotham
Ashalatha, K.
Reddy, D. Kumar
Babu, B. Chinna
Venkateswarlu, Y.
SYNTHESIS-STUTTGART, 2011, (19): : 3180 - 3184
[22] Concise and practical synthesis of (2S,3R,4R,5R) and (2S,3R,4R,5S)-1,6-dideoxy-1,6-iminosugars
Tilekar, JN
Patil, NT
Jadhav, HS
Dhavale, DD
TETRAHEDRON, 2003, 59 (11) : 1873 - 1876
[23] Total synthesis of C-31-methyl ketone apocarotenoids .4. First total synthesis of (3S,5R,6R)-paracentrone
Haugan, JA
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (18): : 2731 - 2737
[24] Synthesis of 3, 4-O-isopropylidene(3S,4S)-dihydroxy-(2R,5R)bis(diphenylphosphino)hexane and its application in Rh-catalyzed highly enantioselective hydrogenation of enamides
Li, W
Zhang, XM
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (18): : 5871 - 5874
[25] Synthesis and crystal structure of (4S,5R)-3,4-dimethyl-5-phenyl-2-(hydroxyethylimino)-1,3-thiazolidine
Gazaliev, Arstan M.
Nurkenov, Oralgazy A.
Turdybekov, Koblandy M.
Fazylov, Serik D.
Ibraev, Marat K.
Turdybekov, Dastan M.
Issabaeva, Meruert B.
MENDELEEV COMMUNICATIONS, 2006, 16 (04) : 243 - 244
[26] Stereocontrolled transformation of nitrohexofuranoses into cyclopentylamines via 2-oxabicyclo[2.2.1]heptanes.: Part 2:: Synthesis of (1S,2R,3S,4S,5R)-3,4,5-trihydroxy-2-aminocyclopentanecarboxylic acid
Soengas, RG
Pampín, MB
Estévez, JC
Estévez, RJ
TETRAHEDRON-ASYMMETRY, 2005, 16 (01) : 205 - 211
[27] ASYMMETRIC-SYNTHESIS .21. ENANTIOSELECTIVE REDUCTION OF KETONES CATALYZED BY NEW (4S,5R)-4,5-DIPHENYL-1,3,2-OXAZABOROLIDINE
JIANG, YZ
QIN, Y
MI, AQ
HUANG, ZT
TETRAHEDRON-ASYMMETRY, 1994, 5 (07) : 1211 - 1214
[28] A NOVEL TRANSFORMATION OF 4 ALDOSES TO SOME OPTICALLY PURE PSEUDOHEXOPYRANOSES AND A PSEUDOPENTOFURANOSE, CARBOCYCLIC ANALOGS OF HEXOPYRANOSES AND PENTOFURANOSE - SYNTHESIS OF DERIVATIVES OF (1S,2S,3R,4S,5S)-2,3,4,5-TETRAHYDROXY-1-(HYDROXYMETHYL)CYCLOHEXANES, (1S,2S,3R,4R,5S)-2,3,4,5-TETRAHYDROXY-1-(HYDROXYMETHYL)CYCLOHEXANES, (1R,2R,3R,4R,5S)-2,3,4,5-TETRAHYDROXY-1-(HYDROXYMETHYL)CYCLOHEXANES, (1S,2S,3R,4S,5R)-2,3,4,5-TETRAHYDROXY-1-(HYDROXYMETHYL)CYCLOHEXANES AND (1S,2S,3S,4S)-2,3,4-TRIHYDROXY-1-(HYDROXYMETHYL)CYCLOPENTANEH
TADANO, KI
MAEDA, H
HOSHINO, M
IIMURA, Y
SUAMI, T
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (10): : 1946 - 1956
[29] SYNTHESIS OF (3R,4R,5R)-1-(TERT-BUTOXYCARBONYL)-3,4-ISOPROPYLIDENEDIOXY-5-METHOXYMETHYL-2-PYRROLIDINONE FROM (S)-PYROGLUTAMINOL
IKOTA, N
CHEMICAL & PHARMACEUTICAL BULLETIN, 1992, 40 (07) : 1925 - 1927
[30] (3R,4S,5R,6R,7S)-3,4,5,7-Tetrahydroxyconidine, an azetidine analogue of 6,7-diepicastanospermine and a conformationally constrained D-deoxyaltronojirimycin, from L-arabinose
Martinez, R. Fernando
Araujo, Noelia
Jenkinson, Sarah F.
Nakagawa, Shinpei
Kato, Atsushi
Fleet, George W. J.
BIOORGANIC & MEDICINAL CHEMISTRY, 2013, 21 (16) : 4813 - 4819

← 1 2 3 4 5 →