Synthesis of N-(β-glycopyranosyl)azidoacetamides

被引：8

作者：

Aich, U ^{[1
]}

Loganathan, D ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Madras 600036, Tamil Nadu, India

来源：

JOURNAL OF CARBOHYDRATE CHEMISTRY | 2005年 / 24卷 / 01期

关键词：

azidoacetamide; carbohydrate; beta-zeolite; N-chloroacetylation;

D O I：

10.1081/CAR-200049402

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

N-(beta-Glycopyranosyl)azidoacetamides, mimetics of the widely distributed GlcNAc-Asn linkage in glycoproteins, have been synthesized in good yields starting from beta-glycopyranosylamines in four steps involving selective N-chloroacetylation, peracetylation catalyzed by Na beta-zeolite, displacement of the Cl group by NaN3 in aqueous acetone, and Zemplen de-O-acetylation.

引用

页码：1 / 12

页数：12

共 21 条

[1] Crystal structures of β-1-N-chloroacetamido derivatives of D-glucose and D-galactose [J].

Aich, U ;

Lakshmanan, T ;

Varghese, B ;

Loganathan, D .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 2003, 22 (09) :891-901

[2]

Bhaskar PM, 1999, SYNLETT, P129

[3] Efficient preparation of natural and synthetic galactosides with a recombinant β-1,4-galactosyltransferase-/UDP-4′-gal epimerase fusion protein [J].

Blixt, O ;

Brown, J ;

Schur, MJ ;

Wakarchuk, W ;

Paulson, JC .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (07) :2442-2448

[4] 2-AZIDOETHYL GLYCOSIDES - GLYCOSIDES POTENTIALLY USEFUL FOR THE PREPARATION OF NEOGLYCOCONJUGATES [J].

CHERNYAK, AY ;

SHARMA, GVM ;

KONONOV, LO ;

KRISHNA, PR ;

LEVINSKY, AB ;

KOCHETKOV, NK ;

RAO, AVR .

CARBOHYDRATE RESEARCH, 1992, 223 :303-309

[5] Syntheses of β,β-difluorotryptamines [J].

Deng, WP ;

Nam, G ;

Fan, JF ;

Kirk, KL .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (07) :2798-2802

[6] Glycobiology: Toward understanding the function of sugars [J].

Dwek, RA .

CHEMICAL REVIEWS, 1996, 96 (02) :683-720

[7]

García-López JJ, 1999, CHEM-EUR J, V5, P1775, DOI 10.1002/(SICI)1521-3765(19990604)5:6<1775::AID-CHEM1775>3.0.CO

[8]

2-2

[9]

GarciaLopez JJ, 1997, SYNLETT, P265

[10] Chemistry and biology of asparagine-linked glycosylation [J].

Imperiali, B ;

O'Connor, SE ;

Hendrickson, T ;

Kellenberger, C .

PURE AND APPLIED CHEMISTRY, 1999, 71 (05) :777-787

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