A facile synthesis of phytosphingosine from diisopropylidene-D-mannofuranose

被引：34

作者：

Chiu, HY ^{[1
]}

Tzou, DLM ^{[1
]}

Patkar, LN ^{[1
]}

Lin, CC ^{[1
]}

机构：

[1] Acad Sinica, Inst Chem, Taipei 115, Taiwan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 14期

关键词：

D O I：

10.1021/jo034224m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In the present study, an efficient method with a high overall yield for preparing phytosphingosine and an analogue was developed. Starting with commercially available 2,3;5,6-di-O-isopropylidene-D-mannofuranose, a variety of lipid moieties were incorporated to obtain phytosphingosine and an analogue. Through an eight-step manipulation, phytosphingosine was obtained with an overall yield of 57%.

引用

页码：5788 / 5791

页数：4

共 55 条

[1] A new diorganozinc-based enantioselective access to truncated D-ribo-phytosphingosine
Ayad, T
Génisson, Y
Verdu, A
Baltas, M
Gorrichon, L
[J]. TETRAHEDRON LETTERS, 2003, 44 (03) : 579 - 582
[2] Stereospecific total syntheses of sphingosine and its analogues from L-serine
Azuma, H
Tamagaki, S
Ogino, K
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (11) : 3538 - 3541
[3] SYNTHESIS OF REACTIVITY OF LAMBDA-5-PHOSPHAZENES - USES AS SYNTHETIC INTERMEDIATES
BARLUENGA, J
PALACIOS, F
[J]. ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1991, 23 (01) : 1 - 65
[4] An epoxide derived from D-glucose as the key intermediate for penaresidine and sphingolipids synthesis
Beauhaire, J
Ducrot, PH
[J]. SYNTHETIC COMMUNICATIONS, 1998, 28 (13) : 2443 - 2456
[5] The synthesis and biological characterization of a ceramide library
Chang, YT
Choi, J
Ding, S
Prieschl, EE
Baumruker, T
Lee, JM
Chung, SK
Schultz, PG
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (09) : 1856 - 1857
[6] REGULATION OF TRANSPLASMALEMMA ELECTRON-TRANSPORT IN OAT MESOPHYLL-CELLS BY SPHINGOID BASES AND BLUE-LIGHT
DHARMAWARDHANE, S
RUBINSTEIN, B
STERN, AI
[J]. PLANT PHYSIOLOGY, 1989, 89 (04) : 1345 - 1350
[7] STEREOCHEMISTRY ASSOCIATED WITH THE ADDITION OF 2-(TRIMETHYLSILYL)THIAZOLE TO DIFFERENTIALLY PROTECTED ALPHA-AMINO ALDEHYDES - APPLICATIONS TOWARD THE SYNTHESIS OF AMINO-SUGARS AND SPHINGOSINES
DONDONI, A
FANTIN, G
FOGAGNOLO, M
PEDRINI, P
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (05) : 1439 - 1446
[8] Double stereodifferentiation in asymmetric dihydroxylation:: application to the first diastereoselective synthesis of L-xylo-[2R,3S,4S]-C18-phytosphingosine
Fernandes, RA
Kumar, P
[J]. TETRAHEDRON LETTERS, 2000, 41 (52) : 10309 - 10312
[9] Total synthesis of α-galactosyl cerebroside
Figueroa-Pérez, S
Schmidt, RR
[J]. CARBOHYDRATE RESEARCH, 2000, 328 (02) : 95 - 102
[10] One-step synthesis of non-anomeric sugar isothiocyanates from sugar azides
García-Moreno, MI
Díaz-Pérez, P
Benito, JM
Mellet, CO
Defaye, J
Fernández, JMG
[J]. CARBOHYDRATE RESEARCH, 2002, 337 (21-23) : 2329 - 2334

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