[(2S,3R,4S,5R,6S)-2-(bromomethyl)-6-methoxy-4,5-bis(methylsulfonyloxy)oxan-3-yl] benzoate | 18944-91-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2S,3R,4S,5R,6S)-2-(bromomethyl)-6-methoxy-4,5-bis(methylsulfonyloxy)oxan-3-yl] benzoate
• CAS: 18944-91-7
• 化学式: C₁₆H₂₁BrO₁₀S₂
• 分子量: 517.373
• InChiKey: DHZVLEPRZCYFPY-SSZWKKLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  148
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  methyl 4,6-O-benzylidene-2,3-di-O-methanesulfonyl-α-D-glucopyranoside 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 氯仿 为溶剂， 以76%的产率得到[(2S,3R,4S,5R,6S)-2-(bromomethyl)-6-methoxy-4,5-bis(methylsulfonyloxy)oxan-3-yl] benzoate
  参考文献：
  名称：

  Facile Bromination of O-Benzylidene Sugar and THP Ethers with NBS in Chloroform in the Presence of AIBN

  摘要：

  N-Bromosuccinimide in chloroform in the presence of a catalytic amount of AIBN is found to cleave O-benzylidene sugar into bromobenzoate in efficient manner. THP-ethers were cleaved into bromides and bromo-esters in high yield.

  DOI：

  10.1080/00397919608003870

文献信息

• Ring opening of 2,3-, 3,4-, and 4,6-O-benzylidene acetals of pyranosides by photobromination with bromotrichloromethane
  作者：Jasbir S. Chana、Peter M. Collins、Farnoosh Farnia、David J. Peacock

  DOI：10.1039/c39880000094

  日期：——

  2,3- 3,4-, and 4,6-O-Benzylidene pyranoside derivatives on photobromination in bromotrichloromethane yield bromo-deoxy-pyranoside benzoates regio- and stereo-specifically which, for the acyl derivatives of the 2,3- and 3,4-acetals, is superior to their reaction with N-bromosuccinimide.

  2,3- 3,4-和4,6- O-苄叉基吡喃糖苷衍生物在溴代三氯甲烷中进行光溴化后，会生成溴-脱氧-吡喃侧苯甲酸苯甲酸酯和立体异构体，对于2,3-和3的酰基衍生物，4-缩醛优于它们与N-溴代琥珀酰亚胺的反应。
• CHANA, JASBIR S.;COLLINS, PETER M.;FARNIA, FARNOOSH;PEACOCK, DAVID J., J. CHEM. SOC. CHEM. COMMUN.,(1988) N 2, 94-96
  作者：CHANA, JASBIR S.、COLLINS, PETER M.、FARNIA, FARNOOSH、PEACOCK, DAVID J.

  DOI：——

  日期：——
• Facile Bromination of O-Benzylidene Sugar and THP Ethers with NBS in Chloroform in the Presence of AIBN
  作者：Sushil Raina、Kamal K. Srivastava、E. Sampath Kumar、Vinod K. Singh

  DOI：10.1080/00397919608003870

  日期：1996.1

  N-Bromosuccinimide in chloroform in the presence of a catalytic amount of AIBN is found to cleave O-benzylidene sugar into bromobenzoate in efficient manner. THP-ethers were cleaved into bromides and bromo-esters in high yield.