[(2R,3R,4S,5R,6S)-3,4,5-tribenzoyloxy-6-[(2R,3R,4S,5R,6S)-6-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxycarbonyloxyoxan-2-yl]methyl benzoate | 228873-34-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [(2R,3R,4S,5R,6S)-3,4,5-tribenzoyloxy-6-[(2R,3R,4S,5R,6S)-6-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxycarbonyloxyoxan-2-yl]methyl benzoate
• CAS: 228873-34-5
• 化学式: C₆₃H₅₈O₁₇
• 分子量: 1087.14
• InChiKey: VIBTVFSUDBSECS-ZQGVGXTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.7
• 重原子数：
  80
• 可旋转键数：
  28
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  196
• 氢给体数：
  0
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5R,6S)-3,4,5-tribenzoyloxy-6-[(2R,3R,4S,5R,6S)-6-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxycarbonyloxyoxan-2-yl]methyl benzoate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以81%的产率得到methyl 4-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-2,3,6-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  An efficient synthesis of mixed β-carbonates of acyl-protected sugar and their decarboxylative glycosidation promoted by trimethylsilyl trifluoromethanesulfonate

  摘要：

  Mixed beta-carbonates of acyl-protected sugar are stereoselectively prepared by using an N-succinimidyl group for activation of the acceptor alcohol carbonate. The glycosyl carbonates are smoothly decarboxylated by trimethylsilyl trifluoromethanesulfonate (Me3SiOTf) to give beta-glycosides preferentially in high yields. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00843-6
• 作为产物：
  描述：

  甲基2,3,6-三-O-苄基-ALPHA-D-吡喃葡萄糖苷 在 potassium carbonate 、 三乙胺 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 240.0h， 生成 [(2R,3R,4S,5R,6S)-3,4,5-tribenzoyloxy-6-[(2R,3R,4S,5R,6S)-6-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxycarbonyloxyoxan-2-yl]methyl benzoate
  参考文献：
  名称：

  An efficient synthesis of mixed β-carbonates of acyl-protected sugar and their decarboxylative glycosidation promoted by trimethylsilyl trifluoromethanesulfonate

  摘要：

  Mixed beta-carbonates of acyl-protected sugar are stereoselectively prepared by using an N-succinimidyl group for activation of the acceptor alcohol carbonate. The glycosyl carbonates are smoothly decarboxylated by trimethylsilyl trifluoromethanesulfonate (Me3SiOTf) to give beta-glycosides preferentially in high yields. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00843-6