Methanesulfonic acid (R)-1-((2S,3S,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-tert-butoxycarbonylamino-tetrahydro-pyran-2-yl)-2-methanesulfonyloxy-ethyl ester | 918416-08-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methanesulfonic acid (R)-1-((2S,3S,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-tert-butoxycarbonylamino-tetrahydro-pyran-2-yl)-2-methanesulfonyloxy-ethyl ester
• 英文别名: [(2R)-2-[(2S,3S,4R,5R,6R)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]-2-methylsulfonyloxyethyl] methanesulfonate
• CAS: 918416-08-7
• 化学式: C₃₆H₄₇NO₁₂S₂
• 分子量: 749.901
• InChiKey: CFXLWWPJGHZZFY-WVJWDQHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  51
• 可旋转键数：
  19
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  179
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid (R)-1-((2S,3S,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-tert-butoxycarbonylamino-tetrahydro-pyran-2-yl)-2-methanesulfonyloxy-ethyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到Methanesulfonic acid (3R,3aS,5R,6R,7R,7aS)-6,7-bis-benzyloxy-5-benzyloxymethyl-octahydro-pyrano[3,2-b]pyrrol-3-yl ester
  参考文献：
  名称：

  Hybrid sugars as glycosidase inhibitors en route to 2-deoxy-2-amino C-glycosyl amino acids

  摘要：

  Sugar-azasugar hybrid molecules made up Of D-galactose with nojirimycin-delta-lactam and pyrrolidine analogues are synthesized using intramolecular cyclization as a key step from 2-nitro galactal and found to be glycosidase inhibitors. Further, some of the intermediate compounds are converted into 2-deoxy-2-amino C-glycosyl glycines and C-glycosyl alanines. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.10.024
• 作为产物：
  描述：

  [(2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((R)-1-hydroxy-2-trityloxy-ethyl)-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester 在 盐酸 、 三乙胺 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 14.0h， 生成 Methanesulfonic acid (R)-1-((2S,3S,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-tert-butoxycarbonylamino-tetrahydro-pyran-2-yl)-2-methanesulfonyloxy-ethyl ester
  参考文献：
  名称：

  Hybrid sugars as glycosidase inhibitors en route to 2-deoxy-2-amino C-glycosyl amino acids

  摘要：

  Sugar-azasugar hybrid molecules made up Of D-galactose with nojirimycin-delta-lactam and pyrrolidine analogues are synthesized using intramolecular cyclization as a key step from 2-nitro galactal and found to be glycosidase inhibitors. Further, some of the intermediate compounds are converted into 2-deoxy-2-amino C-glycosyl glycines and C-glycosyl alanines. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.10.024

文献信息

• Hybrid sugars as glycosidase inhibitors en route to 2-deoxy-2-amino C-glycosyl amino acids
  作者：K. Jayakanthan、Yashwant D. Vankar

  DOI：10.1016/j.tetlet.2006.10.024

  日期：2006.12

  Sugar-azasugar hybrid molecules made up Of D-galactose with nojirimycin-delta-lactam and pyrrolidine analogues are synthesized using intramolecular cyclization as a key step from 2-nitro galactal and found to be glycosidase inhibitors. Further, some of the intermediate compounds are converted into 2-deoxy-2-amino C-glycosyl glycines and C-glycosyl alanines. (c) 2006 Elsevier Ltd. All rights reserved.