Concise synthesis of C-1-cyano-iminosugars via a new Staudinger/aza Wittig/Strecker multicomponent reaction strategy

被引：17

作者：

Zoidl, Manuel ^{[1
]}

Mueller, Bernhard ^{[1
]}

Torvisco, Ana ^{[2
]}

Tysoe, Christina ^{[4
]}

Benazza, Mohamed ^{[3
]}

Siriwardena, Aloysius ^{[3
]}

Withers, Stephen G. ^{[4
]}

Wrodnigg, Tanja M. ^{[1
]}

机构：

[1] Graz Univ Technol, Inst Organ Chem, Glycogrp, A-8010 Graz, Austria

[2] Graz Univ Technol, Inst Inorgan Chem, A-8010 Graz, Austria

[3] Univ Picardie Jules Verne, CNRS FRE 3517, Labe Glycochim Antimicrobiens & Agroressources, F-80039 Amiens, France

[4] Univ British Columbia, Dept Chem, Vancouver, BC V6T 1Z1, Canada

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2014年 / 24卷 / 12期

关键词：

Glycosidase inhibitor; Iminoalditol; Staudinger/aza Wittig Strecker; multicomponent reaction; Glucocerebrosidase; C-1-cyano-iminosugar building blocks; PHARMACOLOGICAL CHAPERONES; GLYCOSIDASE INHIBITORS; NATURAL OCCURRENCE; IMINOSUGARS; DISEASE; G(M1)-GANGLIOSIDOSIS; ALZHEIMERS;

D O I：

10.1016/j.bmcl.2014.03.069

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A new Staudinger/aza Wittig/Strecker multicomponent reaction sequence to C-1-cyano iminoalditols has been developed. When applied to 5-azidodeoxy-D-xylose and -D-glucose as substrates the method leads smoothly in good yield and with excellent stereoselectivity to respectively, 1,5-dideoxy-1,5-imino-D-idurono nitrile and 2,6-didesoxy-2,6-imino-D-glycero-D-ido-heptononitrile. (C) 2014 Published by Elsevier Ltd.

引用

页码：2777 / 2780

页数：4

共 50 条

[41] One-Pot Synthesis of 2,4,5-Trisubstituted Oxazoles via a Tandem Passerini Three-Component Coupling/Staudinger/Aza-Wittig/Isomerization Reaction
Wang, Long
Ren, Zhi-Lin
Chen, Min
Ding, Ming-Wu
SYNLETT, 2014, 25 (05) : 721 - 723
[42] Sequential MCR via Staudinger/Aza-Wittig versus Cycloaddition Reaction to Access Diversely Functionalized 1-Amino-1H-Imidazole-2(3H)-Thiones
Ciccolini, Cecilia
Mari, Giacomo
Favi, Gianfranco
Mantellini, Fabio
De Crescentini, Lucia
Santeusanio, Stefania
MOLECULES, 2019, 24 (20):
[43] Facile synthesis of pyrazino[2,3-e][1,4]diazepine derivatives via the intramolecular aza-Wittig reaction
Okawa, T
Eguchi, S
TETRAHEDRON LETTERS, 1996, 37 (01) : 81 - 84
[44] The First Solvent-Free, Microwave-Accelerated, Three-Component Synthesis of Thiazolidin-4-ones via One-Pot Tandem Staudinger/aza-Wittig Reaction
Shanmugavelan, Poovan
Sathishkumar, Murugan
Nagarajan, Sangaraiah
Ranganathan, Raja
Ponnuswamy, Alagusundaram
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2014, 51 (04) : 1004 - 1011
[45] An efficient synthesis for pyrimido[4',5':4,5]thieno[2,3-c]pyridazine derivatives via intramolecular Aza-Wittig reaction-heterocyclization strategy
Quintela, JM
AlvarezSarandes, R
Veiga, MC
Peinador, C
HETEROCYCLES, 1997, 45 (07) : 1319 - 1336
[46] Facile synthesis of pyrazino[2,3-e][1,4]diazepine derivatives via the intramolecular aza-Wittig reaction
Okawa, T.
Eguchi, S.
Tetrahedron Letters, 37 (01):
[47] Synthesis of Luminescent Indolo[2,1-b]quinazolin-6(12H)-ones via a Sequential Ugi/Iodine-Promoted Cyclization/Staudinger/Aza-Wittig Reaction
Yang, Mao-Lin
Zhao, Long
Chen, Hao-Ran
Ding, Ming-Wu
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (23): : 16424 - 16434
[48] Synthesis of new 1,2,4-oxadiazolidin-5-ylthiophenes and thienopyrimidine derivatives by aza-Wittig reaction using a thienyl carbodiimide
Afaf M.Abdel Hameed
ChineseChemicalLetters, 2012, 23 (04) : 411 - 414
[49] A new approach to the pyrrolo[3,4-d] pyrimidine system via tandem Staudinger/aza-Wittig reaction of 5-acyl-4-azidomethyl-3,4-dihydropyrimidin-2(1H)-ones
Fesenko, Anastasia A.
Grigoriev, Mikhail S.
Shutalev, Anatoly D.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2023, 59 (11-12) : 793 - 798
[50] Synthesis of new 1,2,4-oxadiazolidin-5-ylthiophenes and thienopyrimidine derivatives by aza-Wittig reaction using a thienyl carbodiimide
Hameed, Afaf M. Abdel
CHINESE CHEMICAL LETTERS, 2012, 23 (04) : 411 - 414

← 1 2 3 4 5 →