Synthetic studies on pterin glycosides: the first synthesis of 2′-O-(α-D-glucopyranosyl)biopterin

被引：16

作者：

Hanaya, Tadashi ^{[1
]}

Baba, Hiroki ^{[1
]}

Toyota, Hiroki ^{[1
]}

Yamamoto, Hiroshi ^{[2
]}

机构：

[1] Okayama Univ, Fac Sci, Dept Chem, Okayama 7008530, Japan

[2] Shujitsu Univ, Sch Pharm, Okayama 7038516, Japan

来源：

TETRAHEDRON | 2009年 / 65卷 / 38期

关键词：

Pterin glycoside; Pteridine; Glycosylation; Protecting group; Total synthesis; BIOPTERIN-ALPHA-GLUCOSIDE; PTERIDINES; TEPIDOPTERIN; LIMIPTERIN; PLATENSIS;

D O I：

10.1016/j.tet.2009.07.043

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

L-Rhamnose was led, in a 14-step-sequence, to N(2)-(N,N-dimethylaminomethylene)-1'-O-(4-methoxybenzyl)-3-[2-(4-nitrophenyl)ethyl]biopterin (23), an appropriately protected precursor for 2'-O-glycosylation, while 4,6-di-O-acetyl-2,3-di-O-(4-methoxybenzyl)-alpha-D-glucopyranosyl bromide (32), a novel glycosyl donor, was efficiently prepared from D-glucose in 8 steps. The first synthesis of 2'-O-(alpha-D-glucopyranosyl)biopterin (2a) was achieved by treatment of the key intermediate 23 with 32 in the presence of silver triflate and tetramethylurea, followed by successive removal of the protecting groups. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：7989 / 7997

页数：9

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