tetrahydropyran-2-yl 2,3-di-O-(4-methoxyphenyl)methyl-4,6-O-(4-methoxyphenyl)methylidene-5-deoxy-5-thio-α-D-glucopyranoside | 865166-84-3

• 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: tetrahydropyran-2-yl 2,3-di-O-(4-methoxyphenyl)methyl-4,6-O-(4-methoxyphenyl)methylidene-5-deoxy-5-thio-α-D-glucopyranoside
• CAS: 865166-84-3
• 化学式: C₃₅H₄₂O₉S
• 分子量: 638.779
• InChiKey: PUOHZCWAVZBPTI-VFIGSHNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.28
• 重原子数：
  45.0
• 可旋转键数：
  12.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  83.07
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  tetrahydropyran-2-yl 2,3-di-O-(4-methoxyphenyl)methyl-4,6-O-(4-methoxyphenyl)methylidene-5-deoxy-5-thio-α-D-glucopyranoside 在 吡啶 、 三氯化铝 、 硼烷-三甲胺络合物 作用下， 以 四氢呋喃 为溶剂， 反应 7.5h， 生成 Acetic acid (2R,3S,4S,5R,6S)-6-acetoxy-4,5-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-thiopyran-3-yl ester
  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 camphor-10-sulfonic acid 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 4.0h， 生成 tetrahydropyran-2-yl 2,3-di-O-(4-methoxyphenyl)methyl-4,6-O-(4-methoxyphenyl)methylidene-5-deoxy-5-thio-α-D-glucopyranoside
  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