i-propyl 6-O-benzyl-3-deoxy-2-O-(2-methoxyethoxymethyl)-β-D-threo-hex-2-enopyranoside | 1251542-42-3

• 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: i-propyl 6-O-benzyl-3-deoxy-2-O-(2-methoxyethoxymethyl)-β-D-threo-hex-2-enopyranoside
• 英文别名: (2R,3R,6R)-5-(2-methoxyethoxymethoxy)-2-(phenylmethoxymethyl)-6-propan-2-yloxy-3,6-dihydro-2H-pyran-3-ol
• CAS: 1251542-42-3
• 化学式: C₂₀H₃₀O₇
• 分子量: 382.454
• InChiKey: ISTNMJYJHUGCOS-MISYRCLQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  甲醇 、 i-propyl 6-O-benzyl-3-deoxy-2-O-(2-methoxyethoxymethyl)-β-D-threo-hex-2-enopyranoside 在 mercury(II) acetate 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 2.17h， 生成 i-propyl 6-O-benzyl-3-deoxy-β-D-threo-hexopyranosid-2-ulose methyl (2-methoxyethoxymethyl) acetal
  参考文献：
  名称：

  Stereoselective synthesis of 2-O-MEM-2,3-unsaturated-β-O-glycosides and elaboration to useful synthetic tools

  摘要：

  The glycosylation of alcohols by the new 2-O-MEM-substituted D-galactal-derived allyl epoxide affords the corresponding alkyl 2-O-MEM-3-deoxy-beta-D-threo-hex-2-enopyranosides through a completely 1,4-regio- and a highly to completely substrate-dependent stereoselective glycosylation processes. The glycosides obtained can be regioselectively transformed into corresponding 3-deoxy-beta-O-glycosides, 3-deoxy-beta-D-threo-hexopyranosid-2-uloses, and 3,4-dideoxy-beta-D-glycero-hex-3-enopyranosid-2-uloses, which are useful synthetic tools for further transformations. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.07.061
• 作为产物：
  描述：

  [(2R,3S,4S)-4-hydroxy-5-(2-methoxyethoxymethoxy)-2-(phenylmethoxymethyl)-3,4-dihydro-2H-pyran-3-yl] methanesulfonate 、 异丙醇 在 potassium tert-butylate 作用下， 反应 12.0h， 以83%的产率得到i-propyl 6-O-benzyl-3-deoxy-2-O-(2-methoxyethoxymethyl)-β-D-threo-hex-2-enopyranoside
  参考文献：
  名称：

  Stereoselective synthesis of 2-O-MEM-2,3-unsaturated-β-O-glycosides and elaboration to useful synthetic tools

  摘要：

  The glycosylation of alcohols by the new 2-O-MEM-substituted D-galactal-derived allyl epoxide affords the corresponding alkyl 2-O-MEM-3-deoxy-beta-D-threo-hex-2-enopyranosides through a completely 1,4-regio- and a highly to completely substrate-dependent stereoselective glycosylation processes. The glycosides obtained can be regioselectively transformed into corresponding 3-deoxy-beta-O-glycosides, 3-deoxy-beta-D-threo-hexopyranosid-2-uloses, and 3,4-dideoxy-beta-D-glycero-hex-3-enopyranosid-2-uloses, which are useful synthetic tools for further transformations. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.07.061

文献信息

• Stereoselective synthesis of 2-O-MEM-2,3-unsaturated-β-O-glycosides and elaboration to useful synthetic tools
  作者：Valeria Di Bussolo、Annalisa Fiasella、Ileana Frau、Lucilla Favero、Paolo Crotti

  DOI：10.1016/j.tetlet.2010.07.061

  日期：2010.9

  The glycosylation of alcohols by the new 2-O-MEM-substituted D-galactal-derived allyl epoxide affords the corresponding alkyl 2-O-MEM-3-deoxy-beta-D-threo-hex-2-enopyranosides through a completely 1,4-regio- and a highly to completely substrate-dependent stereoselective glycosylation processes. The glycosides obtained can be regioselectively transformed into corresponding 3-deoxy-beta-O-glycosides, 3-deoxy-beta-D-threo-hexopyranosid-2-uloses, and 3,4-dideoxy-beta-D-glycero-hex-3-enopyranosid-2-uloses, which are useful synthetic tools for further transformations. (C) 2010 Elsevier Ltd. All rights reserved.