N-(2-Azido-3,4,6-tri-O-benzyl-2-desoxy-β-D-glucopyranosyl)-trichloracetamid | 106567-65-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(2-Azido-3,4,6-tri-O-benzyl-2-desoxy-β-D-glucopyranosyl)-trichloracetamid
• 英文别名: 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl β-trichloroacetimidate；N-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)trichloroacetamide
• CAS: 106567-65-1
• 化学式: C₂₉H₂₉Cl₃N₄O₅
• 分子量: 619.932
• InChiKey: KFFPNOXHSJXAIR-RFNQJFSXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.26
• 重原子数：
  41.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  114.78
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1,2:5,6-Di-O-cyclohexyliden-myoinositol-3-benzoat 、 N-(2-Azido-3,4,6-tri-O-benzyl-2-desoxy-β-D-glucopyranosyl)-trichloracetamid 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 (3a'R,4'R,5'S,5a'R,8a'R,8b'S)-4'-(((2S,3R,4R,5S,6R)-3-azido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)hexahydrodispiro[cyclohexane-1,2'-benzo[1,2-d:3,4-d']bis([1,3]dioxole)-7',1''-cyclohexan]-5'-yl benzoate 、
  参考文献：
  名称：

  GPI membrane anchors: synthesis and functional evaluation of aminoglucosyl phosphatidylinositol core analogs

  摘要：

  DOI：

  10.1016/0960-894x(96)00306-x
• 作为产物：
  描述：

  2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 以39%的产率得到tert-Butyldimethylsilyl-2-azido-4-O-(2-azido-3,4,6-tri-O-benzyl-2-desoxy-β-D-glucopyranosyl)-6-O-(tert-butyldimethylsilyl)-2-desoxy-3-O-<(R)-1-(methoxycarbonyl)ethyl>-β-D-glucopyranosid
  参考文献：
  名称：

  Kinzy, Willy; Schmidt, Richard R., Liebigs Annalen der Chemie, 1987, p. 407 - 415

  摘要：

  DOI：

文献信息

• A highly stereoselective construction of 1,2-trans-β-glycosidic linkages capitalizing on 2-azido-2-deoxy-d-glycosyl diphenyl phosphates as glycosyl donors
  作者：Toshifumi Tsuda、Seiichi Nakamura、Shunichi Hashimoto

  DOI：10.1016/j.tet.2004.08.076

  日期：2004.11

  The scope of TMSOTf-promoted glycosidation of 2-azido-2-deoxyglycopyranosyl diphenyl phosphates is investigated. The 3,4,6-tri-O-benzyl-protected glucosyl and galactosyl donors and the 4,6-O-benzylidene-protected galactosyl donor each react with a range of acceptor alcohols in the presence of a stoichiometric amount of TMSOTf in propionitrile at -78 degreesC to afford 1,2-trans-beta-linked disaccharides in high yields with alpha:beta ratios ranging from 9:91 to 1: > 99, regardless of the anomeric composition of the donor used. The use of propionitrile as a solvent at -78 degreesC has proven to be among the best choice for the highest levels of beta-selectivity reported to date for this type of glycosidation. A plausible reaction mechanism, which features a large equilibrium preference for alpha-glycosyl-nitrilium ions over beta-nitrilium ions, is proposed based on byproducts formed through their intermediacy and accounts for the observed excellent beta-selectivities. (C) 2004 Elsevier Ltd. All rights reserved.