methyl 2,3,6-tri-O-benzyl-4-S-(2,3,4-tri-O-benzyl-6-O-tert-butyldiphenylsilyl-β-D-glucopyranosyl)-4-thio-α-D-galactopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,6-tri-O-benzyl-4-S-(2,3,4-tri-O-benzyl-6-O-tert-butyldiphenylsilyl-β-D-glucopyranosyl)-4-thio-α-D-galactopyranoside
• 英文别名: tert-butyl-[[(2R,3R,4S,5R,6S)-6-[(2R,3S,4R,5R,6S)-6-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]sulfanyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy]-diphenylsilane
• 化学式: C₇₁H₇₈O₁₀SSi
• 分子量: 1151.55
• InChiKey: QYEFGFTYSPKQRT-NUZQAKRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.9
• 重原子数：
  83
• 可旋转键数：
  28
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  烯丙基-2,3,4-三-苄氧基-ALPHA-D-葡萄糖苷 在 RhCl(PPh₃)3 哌啶 、 三乙烯二胺 、 N,N-dimethoxy-4-amino-pyridine 、 iminophosphorane base BEMP 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 25.17h， 生成 methyl 2,3,6-tri-O-benzyl-4-S-(2,3,4-tri-O-benzyl-6-O-tert-butyldiphenylsilyl-β-D-glucopyranosyl)-4-thio-α-D-galactopyranoside
  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

文献信息

• Highly efficient synthesis of 1-thioglycosides in solution and solid phase using iminophosphorane bases
  作者：Weizheng Xu、Shawn A. Springfield、John T. Koh

  DOI：10.1016/s0008-6215(99)00327-4

  日期：2000.4

  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.