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.
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收藏
页码：5633 / 5636
页数：4
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共 38 条
  • [1] Direct synthesis of isothiocyanates from isonitriles by molybdenum-catalyzed sulfur transfer with elemental sulfur
    Adam, W
    Bargon, RM
    Bosio, SG
    Schenk, WA
    Stalke, D
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (20) : 7037 - 7041
  • [2] ANODIC GLYCOSYLATION FROM ARYL THIOGLYCOSIDES
    BALAVOINE, G
    GREF, A
    FISCHER, JC
    LUBINEAU, A
    [J]. TETRAHEDRON LETTERS, 1990, 31 (40) : 5761 - 5764
  • [3] Catalytic asymmetric oxidative couplings of 2-naphthols by tridentate N-ketopinidene-based vanadyl dicarboxylates
    Barhate, NB
    Chen, CT
    [J]. ORGANIC LETTERS, 2002, 4 (15) : 2529 - 2532
  • [4] A convergent ring-closing metathesis approach to carbohydrate-based macrolides with potential antibiotic activity
    Blom, P
    Ruttens, B
    Van Hoof, S
    Hubrecht, I
    Van der Eycken, J
    Sas, B
    Van hemel, J
    Vandenkerckhove, J
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (24) : 10109 - 10112
  • [5] Mirror-image carbohydrates: Synthesis of the unnatural enantiomer of a blood group trisaccharide
    Boulineau, FP
    Wei, A
    [J]. 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
    Chen, CT
    Munot, YS
    [J]. 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
    Chen, CT
    Weng, SS
    Kao, JQ
    Lin, CC
    Jan, MD
    [J]. ORGANIC LETTERS, 2005, 7 (15) : 3343 - 3346
  • [8] Nucleophilic acyl substitutions of anhydrides with protic nucleophiles catalyzed by amphoteric, oxomolybdenum species
    Chen, CT
    Kuo, JH
    Pawar, VD
    Munot, YS
    Weng, SS
    Ku, CH
    Liu, CY
    [J]. 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
    Chen, CT
    Kuo, JH
    Ku, CH
    Weng, SS
    Liu, CY
    [J]. 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
    Chen, CT
    Lin, JS
    Kuo, JH
    Weng, SS
    Cuo, TS
    Lin, YW
    Cheng, CC
    Huang, YC
    Yu, JK
    Chou, PT
    [J]. ORGANIC LETTERS, 2004, 6 (24) : 4471 - 4474
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