2,3:4,6-di-O-diphenylmethylene-α-D-glucopyranoside | 220835-88-1

• 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: 2,3:4,6-di-O-diphenylmethylene-α-D-glucopyranoside
• 英文别名: (1R,2S,6R,7S,9R)-7-methoxy-4,4,12,12-tetraphenyl-3,5,8,11,13-pentaoxatricyclo[7.4.0.02,6]tridecane
• CAS: 220835-88-1
• 化学式: C₃₃H₃₀O₆
• 分子量: 522.598
• InChiKey: JKIARKMMKYVJMK-SAEUYMBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  39
• 可旋转键数：
  5
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3:4,6-di-O-diphenylmethylene-α-D-glucopyranoside 在 氢氧化钾 作用下， 以 乙醚 、 二甲基亚砜 、 苯 为溶剂， 反应 5.5h， 生成 (4aR,6S,7R,8S,8aR)-6,7-Dimethoxy-2,2-diphenyl-8-trityloxy-hexahydro-pyrano[3,2-d][1,3]dioxine
  参考文献：
  名称：

  A simple procedure for the development of acid-labile protecting groups on position 2 and 3 of methyl α-D-glucopyranoside

  摘要：

  Building blocks of methyl alpha-D-glucopyranoside possessing free hydroxyl functions in the position 2 or 3 and orthogonal acid-labile protecting groups on the other reacting sites can be conveniently prepared by means of benzophenone dimethyl ketal under very mild experimental conditions. Trityl and diphenylmethoxymethyl groups have been easily built on secondary hydroxyl groups of monosaccharides for the first time. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02512-x
• 作为产物：
  描述：

  苯甲酮二甲基缩酮 、 alpha-甲基葡萄糖甙 在 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 以40%的产率得到2,3:4,6-di-O-diphenylmethylene-α-D-glucopyranoside
  参考文献：
  名称：

  A simple procedure for the development of acid-labile protecting groups on position 2 and 3 of methyl α-D-glucopyranoside

  摘要：

  Building blocks of methyl alpha-D-glucopyranoside possessing free hydroxyl functions in the position 2 or 3 and orthogonal acid-labile protecting groups on the other reacting sites can be conveniently prepared by means of benzophenone dimethyl ketal under very mild experimental conditions. Trityl and diphenylmethoxymethyl groups have been easily built on secondary hydroxyl groups of monosaccharides for the first time. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02512-x

文献信息

• A simple procedure for the development of acid-labile protecting groups on position 2 and 3 of methyl α-D-glucopyranoside
  作者：Leonardo Di Donna、Anna Napoli、Carlo Siciliano、Giovanni Sindona

  DOI：10.1016/s0040-4039(98)02512-x

  日期：1999.1

  Building blocks of methyl alpha-D-glucopyranoside possessing free hydroxyl functions in the position 2 or 3 and orthogonal acid-labile protecting groups on the other reacting sites can be conveniently prepared by means of benzophenone dimethyl ketal under very mild experimental conditions. Trityl and diphenylmethoxymethyl groups have been easily built on secondary hydroxyl groups of monosaccharides for the first time. (C) 1999 Elsevier Science Ltd. All rights reserved.