Carbonic acid benzyl ester (2S,3R,4S,5S,6R)-4,5-bis-benzyloxycarbonyloxy-2-methoxy-6-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-pyran-3-yl ester | 197630-99-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: Carbonic acid benzyl ester (2S,3R,4S,5S,6R)-4,5-bis-benzyloxycarbonyloxy-2-methoxy-6-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-pyran-3-yl ester
• 英文别名: benzyl [(2S,3R,4S,5S,6R)-2-methoxy-6-[[(4-methoxyphenyl)-diphenylmethoxy]methyl]-3,5-bis(phenylmethoxycarbonyloxy)oxan-4-yl] carbonate
• CAS: 197630-99-2
• 化学式: C₅₁H₄₈O₁₃
• 分子量: 868.934
• InChiKey: PSQVKJVSPTWIRA-YECKJZEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  64
• 可旋转键数：
  23
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  144
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  Carbonic acid benzyl ester (2S,3R,4S,5S,6R)-4,5-bis-benzyloxycarbonyloxy-2-methoxy-6-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-pyran-3-yl ester 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 3.0h， 以90%的产率得到Carbonic acid benzyl ester (2R,3S,4S,5R,6S)-4,5-bis-benzyloxycarbonyloxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  The Benzyloxycarbonyl Protective Group : a Good Alternative to the Benzyl Protective Group in the Glycopyranoside and Glycofuranoside Series

  摘要：

  A procedure for the O-benzyloxycarbonylation of secondary alcohols in the glucose, galactose, mannose, ribose and deoxyribose series is described. Starting from the (4-methoxy)tritylated derivatives on the primary hydroxyl group, the fully protected compounds were obtained for the first time in high yields. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)10021-1
• 作为产物：
  描述：

  氯甲酸苄酯 、 methyl 6-O-(4-methoxytrityl)-α-D-galactopyranoside 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以90%的产率得到Carbonic acid benzyl ester (2S,3R,4S,5S,6R)-4,5-bis-benzyloxycarbonyloxy-2-methoxy-6-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  The Benzyloxycarbonyl Protective Group : a Good Alternative to the Benzyl Protective Group in the Glycopyranoside and Glycofuranoside Series

  摘要：

  A procedure for the O-benzyloxycarbonylation of secondary alcohols in the glucose, galactose, mannose, ribose and deoxyribose series is described. Starting from the (4-methoxy)tritylated derivatives on the primary hydroxyl group, the fully protected compounds were obtained for the first time in high yields. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)10021-1