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

[31] Asymmetric synthesis of non-natural amino acid derivatives: (2R/3S) and (2S/3R) 2-(tert-butoxycarbonylamino)-3-cyclohexyl-3-phenyl propanoic acids [J].

Yang, Rui ;

Guo, Ya-Fei ;

Gao, Zhan-Yong ;

Zhao, Qian ;

Zhang, Qian-Yang ;

Lin, Jun .

JOURNAL OF CHEMICAL RESEARCH, 2015, (02) :86-89

[32] Synthetic studies on homophymine A: stereoselective synthesis of (2R,3R,4R,6R)-3-hydroxy-2,4,6-trimethyloctanoic acid [J].

Bellotta, Filomena ;

D'Auria, Maria Valeria ;

Sepe, Valentina ;

Zampella, Angela .

TETRAHEDRON, 2009, 65 (18) :3659-3663

[33] The first asymmetric total syntheses of 3((1R,2R)- and 3((1S,2R)-2-(12-methyltridecyl)cyclopropyl)propanoic acid [J].

Mohapatra, Debendra K. ;

Guguloth, Nagesh ;

Yadav, J. S. .

TETRAHEDRON LETTERS, 2012, 53 (49) :6718-6720

[34] A flexible carbanionic approach to protected trans-(2R,3S)-2-substituted 3-aminopyrrolidines:: application to the asymmetric synthesis of (+)-absouline [J].

Tang, T ;

Ruan, YP ;

Ye, JL ;

Huang, PQ .

SYNLETT, 2005, (02) :231-234

[35] Stereodivergent approach to both syn- and anti-isomers of γ-amino-β-hydroxy acids: (3S,4S)- and (3R,4S)-AHPPA derivatives [J].

Yoo, Dongwon ;

Song, Jeeyun ;

Kang, Moon Sung ;

Kang, Eun-Sil ;

Kim, Young Gyu .

TETRAHEDRON-ASYMMETRY, 2011, 22 (16-17) :1700-1704

[36] The rel-(2R,3S)-2-((Diphenylmethylene)amino)-5-oxo-5-phenyl-3-(thiophen-2-yl)pentanenitrile [J].

Tasheva, Donka N. ;

Mihaylova, Vesela M. .

MOLBANK, 2024, 2024 (03)

[37] Asymmetric synthesis of (2S,3S)- and (2R,3R)-α,β-dialkyl-α-amino acids via alkylation of chiral nickel(II) complexes of aliphatic α-amino acids with racemic α-alkylbenzyl bromides [J].

Soloshonok, Vadim A. ;

Boettiger, Thomas U. ;

Bolene, Shawna B. .

SYNTHESIS-STUTTGART, 2008, (16) :2594-2602

[38] ASYMMETRIC-SYNTHESIS OF ORGANOELEMENTAL ANALOGS OF NATURAL COMPOUNDS .7. (2R,3S)-2-AMINO-3-HYDROXY-5-PHOSPHONOVALERIC ACID [J].

SOLOSHONOK, VA ;

SVISTUNOVA, NY ;

KUKHAR, VP ;

GUDIMA, AO ;

KUZMINA, NA ;

BELOKON, YN .

BULLETIN OF THE RUSSIAN ACADEMY OF SCIENCES-DIVISION OF CHEMICAL SCIENCE, 1992, 41 (05) :922-925

[39] Stereoselective synthesis of N-benzyl (2S,3S,4S)-3-hydroxy-4-methylproline [J].

Hiremath, Mahanthaswamy ;

Kumar, Yalechakanahalli C. Sunil ;

Umashankara, Muddegowda ;

Sandhya, Nagarakere C. ;

Chandrappa, Siddapa ;

Kumar, Chottanahalli S. Pavan ;

Mantelingu, Kempegowda ;

Rangappa, Kanchugarakoppalu S. .

TETRAHEDRON-ASYMMETRY, 2016, 27 (06) :261-267

[40] Preparation and characterization of [5-13C]-(2S,4R)-leucine and [4-13C]-(2S,3S)-valine -: Establishing synthetic schemes to prepare any site-directed isotopomer of L-leucine, L-isoleucine and L-valine [J].

Siebum, AHG ;

Woo, WS ;

Lugtenburg, J .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (23) :4664-4678

← 1 2 3 4 5 →