Regioselective Protection of Sugars Catalyzed by Dimethyltin Dichloride

被引：115

作者：

Demizu, Yosuke ^{[1
]}

Kubo, Yuki ^{[1
]}

Miyoshi, Hiroko ^{[1
]}

Maki, Toshihide ^{[1
]}

Matsumura, Yoshihiro ^{[1
]}

Moriyama, Noriaki ^{[1
]}

Onomura, Osamu ^{[1
]}

机构：

[1] Nagasaki Univ, Grad Sch Biomed Sci, Nagasaki 8528521, Japan

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 21期

基金：

日本学术振兴会;

关键词：

D O I：

10.1021/ol802095e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first catalytic process for protection of hydroxyl groups in sugars has been developed. Highly regioselective protection was accomplished along with high chemical yield. The regioselectivity of the benzoylation was realized as an intrinsic character of sugars based on a stereorelationship among their hydroxyl groups. Furthermore, complete protection of alpha-methyl glucoside and beta-methyl xyloside was accomplished.

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收藏

页码：5075 / 5077

页数：3

相关论文

共 18 条

[1] Strategies in oligosaccharide synthesis [J].

Boons, GJ .

TETRAHEDRON, 1996, 52 (04) :1095-1121

[2] Formal synthesis of (+)3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) via desymmetrization by ring-closing metathesis [J].

Burke, SD ;

Voight, EA .

ORGANIC LETTERS, 2001, 3 (02) :237-240

[3] A convenient and practical method for the selective benzoylation of primary hydroxyl groups using microwave heating [J].

Caddick, S ;

McCarroll, AJ ;

Sandham, DA .

TETRAHEDRON, 2001, 57 (29) :6305-6310

[4] Chemo- and stereoselective monobenzoylation of 1,2-diols catalyzed by organotin compounds [J].

Iwasaki, F ;

Maki, T ;

Onomura, O ;

Nakashima, W ;

Matsumura, Y .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (04) :996-1002

[5] A catalytic one-step process for the chemo- and regioselective acylation of Monosaccharides [J].

Kawabata, Takeo ;

Muramatsu, Wataru ;

Nishio, Tadashi ;

Shibata, Takeshi ;

Schedel, Hartmut .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (42) :12890-12895

[6] A new convenient method for selective monobenzoylation of diols [J].

Maki, T ;

Iwasaki, F ;

Matsumura, Y .

TETRAHEDRON LETTERS, 1998, 39 (31) :5601-5604

[7] Catalytic regioselective sulfonylation of α-chelatable alcohols:: Scope and mechanistic insight [J].

Martinelli, MJ ;

Vaidyanathan, R ;

Pawlak, JM ;

Nayyar, NK ;

Dhokte, UP ;

Doecke, CW ;

Zollars, LMH ;

Moher, ED ;

Van Khau, V ;

Kosmrlj, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (14) :3578-3585

[8]

MATSUMURA Y, 2001, Patent No. 2001247592

[9] Molecular recognition of carbohydrates by zinc porphyrins: Lewis acid Lewis base combinations as a dominant factor for their selectivity [J].

Mizutani, T ;

Kurahashi, T ;

Murakami, T ;

Matsumi, N ;

Ogoshi, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (38) :8991-9001

[10] SELECTIVE FORMATION OF 2 ESTERS OF SOME METHYL ALPHA-DEUTERIUM-HEXOPYRANOSIDES VIA DIBUTYLSTANNYLENE DERIVATIVES [J].

MUNAVU, RM ;

SZMANT, HH .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (10) :1832-1836