Methanesulfonic acid (R)-1-((2S,3R,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-tert-butoxycarbonylamino-tetrahydro-pyran-2-yl)-2-hydroxy-ethyl ester | 918416-17-8

• 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,3R,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-tert-butoxycarbonylamino-tetrahydro-pyran-2-yl)-2-hydroxy-ethyl ester
• 英文别名: [(1R)-2-hydroxy-1-[(2S,3R,4R,5R,6R)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]ethyl] methanesulfonate
• CAS: 918416-17-8
• 化学式: C₃₅H₄₅NO₁₀S
• 分子量: 671.809
• InChiKey: VUAXAWRZVGNAFG-BFZJMCNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  47
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  147
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid (R)-1-((2S,3R,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-tert-butoxycarbonylamino-tetrahydro-pyran-2-yl)-2-hydroxy-ethyl ester 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 [(2S,3S,4R,5R,6R)-2-((S)-1-Azido-2-hydroxy-ethyl)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl 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：

  ((2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-vinyl-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester 在 盐酸 、 四氧化锇 、 N-甲基吗啉氧化物 、 三乙胺 作用下， 以 二氯甲烷 、 氯仿 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 52.0h， 生成 Methanesulfonic acid (R)-1-((2S,3R,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-tert-butoxycarbonylamino-tetrahydro-pyran-2-yl)-2-hydroxy-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.