1,2,3,4-tetra-O-benzoyl-6-O-tert-butyldiphenylsilyl-5-deoxy-5-thio-α-D-glucopyranose | 865167-19-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,2,3,4-tetra-O-benzoyl-6-O-tert-butyldiphenylsilyl-5-deoxy-5-thio-α-D-glucopyranose
• CAS: 865167-19-7
• 化学式: C₅₀H₄₆O₉SSi
• 分子量: 851.061
• InChiKey: KMIDELFQBLPKIX-GJPBNLNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.54
• 重原子数：
  61.0
• 可旋转键数：
  13.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  114.43
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetra-O-benzoyl-6-O-tert-butyldiphenylsilyl-5-deoxy-5-thio-α-D-glucopyranose 在 四丁基氟化铵 、 三乙基硅基三氟甲磺酸酯 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 1,2,3,4-tetra-O-benzoyl-6-O-[2',3',4',6'-tetra-O-benzoyl-5'-deoxy-5'-thio-β-D-glucopyranosyl]-5-thio-α-D-glucopyranose
  参考文献：
  名称：

  Synthetic studies on oligosaccharides composed of 5-thioglucopyranose units

  摘要：

  Glycosylation reactions of 5-thioglucopyranosyl trichloroacetimidates bearing ethereal protective groups at the 2-O-position 14-15, and 37 proceed smoothly to give alpha-glycosides stereoselectively by using a catalytic amount of silyl triflate. This methodology allowed us to achieve syntheses of sulfur-substituted isomaltotetraoside 2 and maltotetraoside 3. These studies also revealed that benzoyl-protected 5-thioglucopyranosyl trichloroacetimidate 12 underwent P-selective glycosylation with C6-OH glucopyranosyl acceptors upon activation by BF3OEt2. This was applied for preparation of sulfur-substituted gentiobiosides 1 and 46. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.05.028
• 作为产物：
  描述：

  tetrahydropyran-2-yl 5-deoxy-5-thio-α-D-glucopyranoside 在 吡啶 、 咪唑 、 高氯酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.0h， 生成 1,2,3,4-tetra-O-benzoyl-6-O-tert-butyldiphenylsilyl-5-deoxy-5-thio-α-D-glucopyranose
  参考文献：
  名称：

  Synthetic studies on oligosaccharides composed of 5-thioglucopyranose units

  摘要：

  Glycosylation reactions of 5-thioglucopyranosyl trichloroacetimidates bearing ethereal protective groups at the 2-O-position 14-15, and 37 proceed smoothly to give alpha-glycosides stereoselectively by using a catalytic amount of silyl triflate. This methodology allowed us to achieve syntheses of sulfur-substituted isomaltotetraoside 2 and maltotetraoside 3. These studies also revealed that benzoyl-protected 5-thioglucopyranosyl trichloroacetimidate 12 underwent P-selective glycosylation with C6-OH glucopyranosyl acceptors upon activation by BF3OEt2. This was applied for preparation of sulfur-substituted gentiobiosides 1 and 46. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.05.028