New entry to pyrrolidine homoazasugars: conversion of D-arabinose into 2,5-anhydro-2,5-imino-D-glucitol via aminohomologation

被引：41

作者：

Dondoni, A ^{[1
]}

Perrone, D ^{[1
]}

机构：

[1] Univ Ferrara, Dipartmento Chim, Chim Organ Lab, I-44100 Ferrara, Italy

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 52期

关键词：

homoazasugars; sugar nitrones; 2-lithiothiazole;

D O I：

10.1016/S0040-4039(99)01987-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The title homoazasugar, also referred as (2R,5S)-bis(hydroxymethyl)-(3R,4R)-dihydroxypyrrolidine, has been synthesized by addition of 2-lithiothiazole to the 2,3,5-tri-O-benzyl-D-arabinofuranose-derived nitrone-hydroxylamine mixture followed by reductive N-dehydroxylation and conversion of the thiazole ring into the hydroxymethyl group. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：9375 / 9378

页数：4

共 14 条

[1] 2,3,5-TRI-O-BENZYL-D-RIBOSYL AND -L-ARABINOSYL BROMIDES [J].

BARKER, R ;

FLETCHER, HG .

JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (11) :4605-&

[2] EXPEDITIOUS SYNTHESIS OF AZASUGARS BY THE DOUBLE REDUCTIVE AMINATION OF DICARBONYL SUGARS [J].

BAXTER, EW ;

REITZ, AB .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (11) :3175-3185

[3] STEREOSELECTIVE HOMOLOGATION - AMINATION OF ALDEHYDES BY ADDITION OF THEIR NITRONES TO C-2 METALATED THIAZOLES - A GENERAL ENTRY TO ALPHA-AMINO ALDEHYDES AND AMINO-SUGARS [J].

DONDONI, A ;

FRANCO, S ;

JUNQUERA, F ;

MERCHAN, FL ;

MERINO, P ;

TEJERO, T ;

BERTOLASI, V .

CHEMISTRY-A EUROPEAN JOURNAL, 1995, 1 (08) :505-520

[4] Grignard addition to aldonitrones.: Stereochemical aspects and application to the synthesis of C2-symmetric diamino alcohols and diamino diols [J].

Dondoni, A ;

Perrone, D ;

Rinaldi, M .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (25) :9252-9264

[5] Applications of sugar nitrones in synthesis: The total synthesis of (+)-polyoxin J [J].

Dondoni, A ;

Franco, S ;

Junquera, F ;

Merchan, FL ;

Merino, P ;

Tejero, T .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (16) :5497-5507

[6] Stereoselective addition of 2-furyllithium and 2-thiazolyllithium to sugar nitrones. Synthesis of carbon-linked glycoglycines [J].

Dondoni, A ;

Junquera, F ;

Merchan, FL ;

Merino, P ;

Scherrmann, MC ;

Tejero, T .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (16) :5484-5496

[7] EFFICACIOUS MODIFICATION OF THE PROCEDURE FOR THE ALDEHYDE RELEASE FROM 2-SUBSTITUTED THIAZOLES [J].

DONDONI, A ;

MARRA, A ;

PERRONE, D .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (01) :275-277

[8] ENANTIOSPECIFIC SYNTHESES OF DEOXYMANNOJIRIMYCIN, FAGOMINE AND 2R,5R-DIHYDROXYMETHYL-3R,4R-DIHYDROXYPYRROLIDINE FROM D-GLUCOSE [J].

FLEET, GWJ ;

SMITH, PW .

TETRAHEDRON LETTERS, 1985, 26 (11) :1469-1472

[9] ALPHA-AMINO ALDEHYDE EQUIVALENTS AS SUBSTRATES FOR RABBIT MUSCLE ALDOLASE - SYNTHESIS OF 1,4-DIDEOXY-D-ARABINITOL AND 2(R),5(R)-BIS(HYDROXYMETHYL)-3(R),4(R)-DIHYDROXYPYRROLIDINE [J].

HUNG, RR ;

STRAUB, JA ;

WHITESIDES, GM .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (12) :3849-3855

[10] A NEW PROCEDURE FOR THE SYNTHESIS OF AZASUGARS [J].

LAY, L ;

NICOTRA, F ;

PAGANINI, A ;

PANGRAZIO, C ;

PANZA, L .

TETRAHEDRON LETTERS, 1993, 34 (28) :4555-4558

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