allyl 2,3,4-tri-O-benzyl-6-O-[4-(tert-butoxycarbonyl)benzyl]-α-D-glucopyranoside | 273935-08-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2,3,4-tri-O-benzyl-6-O-[4-(tert-butoxycarbonyl)benzyl]-α-D-glucopyranoside
• CAS: 273935-08-3
• 化学式: C₄₂H₄₈O₈
• 分子量: 680.838
• InChiKey: VSHMXJZYYUXRDU-GCKSPRBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.84
• 重原子数：
  50.0
• 可旋转键数：
  17.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  81.68
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  allyl 2,3,4-tri-O-benzyl-6-O-[4-(tert-butoxycarbonyl)benzyl]-α-D-glucopyranoside 在 RhCl(PPh₃)3 三乙烯二胺 、 三氟化硼乙醚 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 22.17h， 生成 2,3,4-tri-O-benzyl-6-O-[4-(tert-butoxycarbonyl)benzyl]-1-S-acetyl-1-thio-β-D-glucopyranose
  参考文献：
  名称：

  Highly efficient synthesis of 1-thioglycosides in solution and solid phase using iminophosphorane bases

  摘要：

  Disaccharides of l-thioglycosides, an important class of glycomimics, can be synthesized by direct S-alkylation in exceptionally high yields when iminophosphorane bases are employed. The reaction conditions employed appear to be general and stereospecific. Axial and equatorial 4-triflates and primary tosylates of alkyl pyranosides provided excellent yields of thio-disaccharides without substantial elimination products. The iminophosphorane bases also proved to be useful in solid support-bound couplings of thioglycosides though with lower efficiency. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00327-4
• 作为产物：
  描述：

  烯丙基-2,3,4-三-苄氧基-ALPHA-D-葡萄糖苷 、 4-溴甲基苯甲酸叔丁酯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以86%的产率得到allyl 2,3,4-tri-O-benzyl-6-O-[4-(tert-butoxycarbonyl)benzyl]-α-D-glucopyranoside
  参考文献：
  名称：

  Highly efficient synthesis of 1-thioglycosides in solution and solid phase using iminophosphorane bases

  摘要：

  Disaccharides of l-thioglycosides, an important class of glycomimics, can be synthesized by direct S-alkylation in exceptionally high yields when iminophosphorane bases are employed. The reaction conditions employed appear to be general and stereospecific. Axial and equatorial 4-triflates and primary tosylates of alkyl pyranosides provided excellent yields of thio-disaccharides without substantial elimination products. The iminophosphorane bases also proved to be useful in solid support-bound couplings of thioglycosides though with lower efficiency. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00327-4