Highly diastereoselective thioglycosylation of functionalized peracetylated glycosides catalyzed by MoO2Cl2

被引：64

作者：

Weng, Shiue-Shien ^{[1
]}

Lin, Yow-Dzer ^{[1
]}

Chen, Chien-Tien ^{[1
]}

机构：

[1] Natl Taiwan Normal Univ, Dept Chem, Taipei, Taiwan

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 24期

关键词：

D O I：

10.1021/ol062375g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Among 18 oxometallic species, MoO2Cl2 was found to be the most reactive in catalytic thioglycosylation of O-acetylated glycosides with functionalized thiols in CH2Cl2, leading cleanly to 1,2-trans-thioglycosides with exclusive diastereocontrol. The new catalytic protocol is applicable to a monoglycoside building block and beta-(1 -> 6)-S-linked-thiodisaccharide synthesis.

引用

页码：5633 / 5636

页数：4

共 38 条

[1] Direct synthesis of isothiocyanates from isonitriles by molybdenum-catalyzed sulfur transfer with elemental sulfur [J].

Adam, W ;

Bargon, RM ;

Bosio, SG ;

Schenk, WA ;

Stalke, D .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (20) :7037-7041

[2] ANODIC GLYCOSYLATION FROM ARYL THIOGLYCOSIDES [J].

BALAVOINE, G ;

GREF, A ;

FISCHER, JC ;

LUBINEAU, A .

TETRAHEDRON LETTERS, 1990, 31 (40) :5761-5764

[3] Catalytic asymmetric oxidative couplings of 2-naphthols by tridentate N-ketopinidene-based vanadyl dicarboxylates [J].

Barhate, NB ;

Chen, CT .

ORGANIC LETTERS, 2002, 4 (15) :2529-2532

[4] A convergent ring-closing metathesis approach to carbohydrate-based macrolides with potential antibiotic activity [J].

Blom, P ;

Ruttens, B ;

Van Hoof, S ;

Hubrecht, I ;

Van der Eycken, J ;

Sas, B ;

Van hemel, J ;

Vandenkerckhove, J .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (24) :10109-10112

[5] Mirror-image carbohydrates: Synthesis of the unnatural enantiomer of a blood group trisaccharide [J].

Boulineau, FP ;

Wei, A .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (10) :3391-3399

[6] Direct atom-efficient esterification between carboxylic acids and alcohols catalyzed by amphoteric, water-tolerant TiO(acac)2 [J].

Chen, CT ;

Munot, YS .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (21) :8625-8627

[7] Stripping off water at ambient temperature: Direct atom-efficient acetal formation between aldehydes and diols catalyzed by water-tolerant and recoverable vanadyl triflate [J].

Chen, CT ;

Weng, SS ;

Kao, JQ ;

Lin, CC ;

Jan, MD .

ORGANIC LETTERS, 2005, 7 (15) :3343-3346

[8] Nucleophilic acyl substitutions of anhydrides with protic nucleophiles catalyzed by amphoteric, oxomolybdenum species [J].

Chen, CT ;

Kuo, JH ;

Pawar, VD ;

Munot, YS ;

Weng, SS ;

Ku, CH ;

Liu, CY .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (04) :1188-1197

[9] Nucleophilic acyl substitutions of esters with protic nucleophiles mediated by amphoteric, oxotitanium, and vanadyl species [J].

Chen, CT ;

Kuo, JH ;

Ku, CH ;

Weng, SS ;

Liu, CY .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (04) :1328-1339

[10] Site-selective DNA photocleavage involving unusual photoinitiated tautomerization of chiral tridentate vanadyl(V) complexes derived from N-salicylidene α-amino acids [J].

Chen, CT ;

Lin, JS ;

Kuo, JH ;

Weng, SS ;

Cuo, TS ;

Lin, YW ;

Cheng, CC ;

Huang, YC ;

Yu, JK ;

Chou, PT .

ORGANIC LETTERS, 2004, 6 (24) :4471-4474

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