Efficient installation of β-mannosides using a dehydrative coupling strategy

被引：74

作者：

Codée, JDC ^{[1
]}

Hossain, LH ^{[1
]}

Seeberger, PH ^{[1
]}

机构：

[1] ETH, Organ Chem Lab, CH-8093 Zurich, Switzerland

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 15期

关键词：

D O I：

10.1021/ol051038p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new coupling procedure for the construction of the challenging beta-mannosidic bond is described. Dehydrative mannosylation using 4,6-O-benzylidene mannopyranoses allows for the formation of beta-mannosides in excellent yield. The stereoselectivity is generally good but influenced by the exact nature of the glycosylating agent and the nucleophile.

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收藏

页码：3251 / 3254

页数：4

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共 24 条

[1] A modular strategy toward the synthesis of heparin-like oligosaccharides using monomeric building blocks in a sequential glycosylation strategy [J].

Codée, JDC ;

Stubba, B ;

Schiattarella, M ;

Overkleeft, HS ;

van Boeckel, CAA ;

van Boom, JH ;

van der Marel, GA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (11) :3767-3773

[2] Chemoselective glycosylations using sulfonium triflate activator systems [J].

Codée, JDC ;

van den Bos, LJ ;

Litjens, REJN ;

Overkleeft, HS ;

van Boeckel, CAA ;

van Boom, JH ;

van der Marel, GA .

TETRAHEDRON, 2004, 60 (05) :1057-1064

[3] Sequential one-pot glycosylations using 1-hydroxyl and 1-thiodonors [J].

Codée, JDC ;

van den Bos, LJ ;

Litjens, REJN ;

Overkleeft, HS ;

van Boom, JH ;

van der Marel, GA .

ORGANIC LETTERS, 2003, 5 (11) :1947-1950

[4] 2-O-propargyl ethers:: Readily cleavable, minimally intrusive protecting groups for β-mannosyl donors [J].

Crich, D ;

Jayalath, P .

ORGANIC LETTERS, 2005, 7 (11) :2277-2280

[5] Direct chemical synthesis of the β-mannans:: Linear and block syntheses of the alternating β-(l→3)-β-(l→4)-mannan common to Rhodotorula glutinis, Rhodotorula mucilaginosa, and Leptospira biflexa [J].

Crich, D ;

Li, WJ ;

Li, HM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) :15081-15086

[6] Direct chemical synthesis of the β-D-mannans:: The β-(1→2) end β-(1→4) series [J].

Crich, D ;

Banerjee, A ;

Yao, QJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (45) :14930-14934

[7] Solid-phase synthesis of β-mannosides [J].

Crich, D ;

Smith, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (30) :8867-8869

[8] Chemistry of glycosyl triflates:: Synthesis of β-mannopyranosides (Reprinted from Glycochemistry:: Principles, Synthesis, and Applications, pg 53-75, 2001) [J].

Crich, D .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 2002, 21 (7-9) :667-690

[9] An unusual example of steric buttressing in glycosylation [J].

Crich, D ;

Dudkin, V .

TETRAHEDRON LETTERS, 2000, 41 (30) :5643-5646

[10] 1-Benzenesulfinyl piperidine/trifluoromethanesulfonic anhydride: A potent combination of shelf-stable reagents for the low-temperature conversion of thioglycosides to glycosyl triflates and for the formation of diverse glycosidic linkages [J].

Crich, D ;

Smith, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (37) :9015-9020