6'-O-(tert-butyldiphenyl)silyl-2,3,3',4,4'-penta-O-benzylsucrose | 1326706-59-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6'-O-(tert-butyldiphenyl)silyl-2,3,3',4,4'-penta-O-benzylsucrose
• 英文别名: [(2R,3R,4S,5R,6R)-6-[(2S,3S,4R,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-(hydroxymethyl)-3,4-bis(phenylmethoxy)oxolan-2-yl]oxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methanol
• CAS: 1326706-59-5
• 化学式: C₆₃H₇₀O₁₁Si
• 分子量: 1031.33
• InChiKey: ZSWQOBYIDKHLLX-YCUXWZMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.31
• 重原子数：
  75
• 可旋转键数：
  25
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  124
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  6'-O-(tert-butyldiphenyl)silyl-2,3,3',4,4'-penta-O-benzylsucrose 在 吡啶 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 三乙胺 、 potassium diphenylphosphine 、 potassium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 82.0h， 生成 6'-deoxy-6'-iodo-2,3,3',4,4'-penta-O-benzylsucrose
  参考文献：
  名称：

  New Methodology for the Differentiation of the Primary Hydroxyl Groups in 2,3,3′,4,4′-Penta-O-Benzylsucrose: Convenient Approach to Sucrose Monophosphines

  摘要：

  Two new routes to derivatives of 2,3,3',4,4'-penta-O-benzylsucrose with differently protected primary hydroxyl groups were elaborated. One of these compounds, 2,3,3',4,4'-penta-O-benzyl-6'-O-mesylsucrose, was used in a model synthesis of the 6'-phosphine with sucrose scaffold. Elimination of the mesyloxy-group under the reaction conditions was also noted providing the 5',6'-unsaturated sucrose derivative.

  DOI：

  10.1080/07328303.2011.556286
• 作为产物：
  描述：

  叔丁基二苯基氯硅烷 、 2,3,3’,4,4’-penta-O-benzylsucrose 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.33h， 以63%的产率得到6'-O-(tert-butyldiphenyl)silyl-2,3,3',4,4'-penta-O-benzylsucrose
  参考文献：
  名称：

  New Methodology for the Differentiation of the Primary Hydroxyl Groups in 2,3,3′,4,4′-Penta-O-Benzylsucrose: Convenient Approach to Sucrose Monophosphines

  摘要：

  Two new routes to derivatives of 2,3,3',4,4'-penta-O-benzylsucrose with differently protected primary hydroxyl groups were elaborated. One of these compounds, 2,3,3',4,4'-penta-O-benzyl-6'-O-mesylsucrose, was used in a model synthesis of the 6'-phosphine with sucrose scaffold. Elimination of the mesyloxy-group under the reaction conditions was also noted providing the 5',6'-unsaturated sucrose derivative.

  DOI：

  10.1080/07328303.2011.556286

文献信息

• Novel Approach to Selectively Functionalized Derivatives of Sucrose
  作者：Sławomir Jarosz、Michał Kowalski、Piotr Cmoch

  DOI：10.1055/s-0033-1340180

  日期：——

  New synthetic routes to complex sucrose derivatives are presented. They are based on a highly selective silylation of the hydroxyl group at the C6' position ('fructose end') in 2,3,3',4,4'-penta-O-benzylsucrose followed by functionalization of the remaining (C-1',6) positions. One of these synthons was used as a chiral platform for the construction of aza-macrocyclic systems.