| 1161782-32-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 1161782-32-6
• 化学式: C₂₆H₂₈O₉S₃
• 分子量: 580.701
• InChiKey: SEOAZTCWIXXBAO-PUHDZGQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.02
• 重原子数：
  38.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  136.43
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  Phenyl 6-O-(p-toluenesulfonyl)-1-thio-α-D-mannopyranoside 、 2,2-二甲氧基丙烷 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 以9.50 g的产率得到Phenyl 2,3-O-isopropylidene-6-O-(p-toluenesulfonyl)-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of orthogonally protected d-olivoside, 1,3-di-O-acetyl-4-O-benzyl-2,6-dideoxy-d-arabinopyranose, as a C-glycosyl donor

  摘要：

  1,3-Di-O-acetyl-4-O-benzyl-2,6-dideoxy-D-arabinopyranose (11) was synthesised from thiophenyl alpha-D-mannopyranoside (21) in an eight-step sequence. Tosylation of 21 and subsequent reaction with 2,2-dimethoxypropane gave tosylate 22, which upon treatment with lithium aluminium hydride furnished 6-deoxy glycoside 24 and by-product thiophenyl 6-deoxy-2-O-isopropyl-alpha-D-arabinopyranoside. The X-ray crystal structure of the latter was determined. Benzylation of the 4-hydroxyl group of 24 and Subsequent protecting group manipulation gave D-rhamnosyl bromide 29, which on treatment with zinc-copper couple gave the orthogonally protected D-rhamnal 30. Triphenylphosphine hydrogen bromide catalysed addition of acetic acid to 30 furnished the target molecule 11. The scandium(III) triflate promoted reaction of 11 and 2-naphthol gave the corresponding C-glycoside 36 in 86% yield. Crown Copyright (C) 2009 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.03.092