A tethered aminohydroxylation route to L-arabino-[2R,3S,4R] and L-xylo-[2R,3S,4S]-C18-phytosphingosines

被引：19

作者：

Dubey, Abhishek ^{[1
]}

Kumar, Pradeep ^{[1
]}

机构：

[1] Natl Chem Lab, Div Organ Chem, Pune 411008, Maharashtra, India

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 26期

关键词：

Sharpless asymmetric kinetic resolution; Tethered aminohydroxylation; Regioselectivity; Stereoselectivity; Phytosphingosine; Sphingolipids; EFFICIENT TOTAL-SYNTHESIS; ASYMMETRIC-SYNTHESIS; ALLYLIC ALCOHOLS; PHYTOSPHINGOSINE; SPHINGOLIPIDS; CERAMIDES; MUCOSA; TA;

D O I：

10.1016/j.tetlet.2009.02.173

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise and highly efficient synthesis of L-arabino-[2R,3S,4R] and L-xylo-[ 2R,3S,4S]-C-18-phytosphingosines has been achieved. The synthetic strategy features the Sharpless kinetic resolution and tethered aminohydroxylation as the key steps. (C) 2009 Elsevier Ltd, All rights reserved.

引用

页码：3425 / 3427

页数：3

共 50 条

[21] Rac-(2R*,3R*)-S-Ethyl-4-Chloro-3-Hydroxy-2-Phenylbuthanethioate and Rac-(2R*, 3R*)-S-Ethyl-2-Phenyl-3-(tosyloxy) buthanethioate: Dichotomy of the Stereoselectivity of the Mukaiyama Reaction [J].

Vallat, Oliver ;

Buciumas, Ana-Maria ;

Neier, Reinhard ;

Stoeckli-Evans, Helen .

JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, 2010, 40 (01) :10-14

[22] Rac-(2R*,3R*)-S-Ethyl-4-Chloro-3-Hydroxy-2-Phenylbuthanethioate and Rac-(2R*,3R*)-S-Ethyl-2-Phenyl-3-(tosyloxy)buthanethioate: Dichotomy of the Stereoselectivity of the Mukaiyama Reaction [J].

Oliver Vallat ;

Ana-Maria Buciumas ;

Reinhard Neier ;

Helen Stoeckli-Evans .

Journal of Chemical Crystallography, 2010, 40 :10-14

[23] Aza variant of intramolecular nucleophile-catalyzed aldol lactonization (NCAL): formal synthesis of (3S,4R) and (3R,4S) 4-(hydroxymethyl)pyrrolidin-3-ol [J].

Sikriwal, Dimpy ;

Dikshit, Dinesh K. .

TETRAHEDRON, 2011, 67 (01) :210-215

[24] Asymmetric synthesis of (-)-(2R, 3R, 6S)-Irnigaine [J].

Ma, N ;

Ma, DW .

CHINESE JOURNAL OF CHEMISTRY, 2003, 21 (10) :1356-1359

[25] Asymmetric Synthesis of (-)-(2R,3R,6S)-Irnigaine [J].

马楠 ;

马大为 .

ChineseJournalofChemistry, 2003, (10) :1356-1359

[26] SYNTHESES OF [18F] LABELED (2S, 3S, 4R)-2-(N-6-[18F]FLUOROHEXANOYLAMINO)- AND 8-[18F]FLUOROOCTANOYLAMINO)OCTADECANE-1,3,4-TRIOL [J].

Moon, B. S. ;

Lee, K. C. ;

An, G. I. ;

Yang, S. D. ;

Chun, K. S. .

JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2005, 48 :S331-S331

[27] Enantioselective total synthesis of (2S,3R,4R)-D-xylo-phytosphingosine from substituted azetidin-2-one [J].

Pandey, Ganesh ;

Tiwari, Dharmendra Kumar .

TETRAHEDRON LETTERS, 2009, 50 (26) :3296-3298

[28] Total synthesis of the acetyl derivatives of lyxo-(2R,3R,4R)-phytosphingosine and (-)-jaspine B [J].

Rao, Ganipisetti Srinivas ;

Chandrasekhar, Bandari ;

Rao, Batchu Venkateswara .

TETRAHEDRON-ASYMMETRY, 2012, 23 (08) :564-569

[29] Crystal Structures of Dipeptides Derived from the β-Amino Acids (1R,2S)-2-Aminocyclopentanecarboxylic Acid and (1S,2R,3S)-2-Amino-3-methylcyclopentanecarboxylic Acid [J].

Abraham, Elin ;

Davies, Stephen G. ;

Roberts, Paul M. ;

Thompson, Amber L. ;

Thomson, James E. .

JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, 2011, 41 (11) :1722-1728

[30] Crystal Structures of Dipeptides Derived from the β-Amino Acids (1R,2S)-2-Aminocyclopentanecarboxylic Acid and (1S,2R,3S)-2-Amino-3-methylcyclopentanecarboxylic Acid [J].

Elin Abraham ;

Stephen G. Davies ;

Paul M. Roberts ;

Amber L. Thompson ;

James E. Thomson .

Journal of Chemical Crystallography, 2011, 41 :1722-1728

← 1 2 3 4 5 →