N-(p-toluenesulfonyl) 2,3,5-tri-O-benzyl-α,β-D-ribofuranosylamine | 1048376-74-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(p-toluenesulfonyl) 2,3,5-tri-O-benzyl-α,β-D-ribofuranosylamine
• 英文别名: N-[(3R,4R,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolan-2-yl]-4-methylbenzenesulfonamide
• CAS: 1048376-74-4
• 化学式: C₃₃H₃₅NO₆S
• 分子量: 573.71
• InChiKey: GKZFKRMTVZBBEW-YOIJXYMPSA-N

物化性质

• 沸点：
  704.0±70.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.39
• 重原子数：
  41.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  83.09
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  甲基 2,3,5-三-O-苄基-D-呋喃核糖苷 、 对甲苯磺酰胺 在 HClO₄ on silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以92%的产率得到N-(p-toluenesulfonyl) 2,3,5-tri-O-benzyl-α,β-D-ribofuranosylamine
  参考文献：
  名称：

  Sulfonamidoglycosylation of Methyl Glycosides Employing Perchloric Acid Supported on Silica Gel

  摘要：

  The sulfonamidoglycosylation of methyl glycosides in the presence of perchloric acid immobilized on silica gel proceeded effectively to afford the corresponding sulfonamido glycosides with good to high yields with minimal workup and short reaction times. This methodology was applied to the synthesis of some N-glycosyl sulfamides, which showed low nanomolar activity against human carbonic anhydrase.

  DOI：

  10.1080/07328300802030829

文献信息

• One-step synthesis of N-protected glycosylamines from sugar hemiacetals
  作者：Virginie Liautard、Christelle Pillard、Valérie Desvergnes、Olivier R. Martin

  DOI：10.1016/j.carres.2007.11.022

  日期：2008.8

  Protected pentofuranose, hexofuranose and hexopyranose hemiacetals were found to react efficiently with amines carrying a deactivating group (alkoxycarbonyl, tosyl or phosphoryl group) in the presence of a Lewis acid to give the corresponding, stable glycosylamines. Such glycosylamine derivatives are useful substrates for further elaboration into nitrogen-containing natural products and carbohydrate mimetics. (C) 2007 Elsevier Ltd. All rights reserved.