(1S,2S,3S,5R)-2-(benzyloxy)-5-(((2R,4aR,6S,7S,8S,8aR)-7-(benzyloxy)-6-methoxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-yl)oxy)-3-((S)-1,2-bis(benzyloxy)ethyl)cyclopentan-1-ol | 1187445-14-2

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (1S,2S,3S,5R)-2-(benzyloxy)-5-(((2R,4aR,6S,7S,8S,8aR)-7-(benzyloxy)-6-methoxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-yl)oxy)-3-((S)-1,2-bis(benzyloxy)ethyl)cyclopentan-1-ol
• CAS: 1187445-14-2
• 化学式: C₄₉H₅₄O₁₀
• 分子量: 802.962
• InChiKey: DGMBWDXMZYPGPL-IXVDTKKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.58
• 重原子数：
  59.0
• 可旋转键数：
  18.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  103.3
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (1S,2S,3S,5R)-2-(benzyloxy)-5-(((2R,4aR,6S,7S,8S,8aR)-7-(benzyloxy)-6-methoxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-yl)oxy)-3-((S)-1,2-bis(benzyloxy)ethyl)cyclopentan-1-ol 、 乙酸酐 以 吡啶 为溶剂， 反应 3.0h， 以89%的产率得到[(1S,2S,3S,5R)-5-[[(2R,4aR,6S,7S,8S,8aR)-6-methoxy-2-phenyl-7-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]-3-[(1S)-1,2-bis(phenylmethoxy)ethyl]-2-phenylmethoxycyclopentyl] acetate
  参考文献：
  名称：

  Carbasugar analogues of galactofuranosides: β-O-linked derivatives and towards β-S-linked derivatives

  摘要：

  A selectively protected carbasugar analogue of beta-galactofuranose was synthesised from glucose using ring-closing metathesis as the key step. The carbasugar was converted into an alpha-galacto configured 1,2-epoxide, which was an effective electrophile in Lewis acid catalysed coupling reactions with alcohols. The epoxide was opened with regioselective attack at C-1 to give beta-galacto configured C-1 ethers. Using carbohydrates as nucleophiles, we synthesised a number of pseudodisaccharides. The epoxide was also regioselectively opened at C-1 with a sulfur nucleophile under basic conditions to give a beta-galacto configured C-1 thioether. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.04.032
• 作为产物：
  描述：

  (2R,4R,5S,6R)-1,2,4-tri-O-benzyl-5,6-O-isopropylidene-1,2,4,5,6-pentahydroxyoct-7-en-3-one 在 盐酸 、 正丁基锂 、 Hoveyda-Grubbs catalyst second generation 、 偶氮二甲酸二异丙酯 、 palladium 10% on activated carbon 、 三氟化硼乙醚 、 氢气 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 溶剂黄146 、 乙酸乙酯 、 甲苯 为溶剂， 反应 5.5h， 生成 (1S,2S,3S,5R)-2-(benzyloxy)-5-(((2R,4aR,6S,7S,8S,8aR)-7-(benzyloxy)-6-methoxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-yl)oxy)-3-((S)-1,2-bis(benzyloxy)ethyl)cyclopentan-1-ol
  参考文献：
  名称：

  Carbasugar analogues of galactofuranosides: β-O-linked derivatives and towards β-S-linked derivatives

  摘要：

  A selectively protected carbasugar analogue of beta-galactofuranose was synthesised from glucose using ring-closing metathesis as the key step. The carbasugar was converted into an alpha-galacto configured 1,2-epoxide, which was an effective electrophile in Lewis acid catalysed coupling reactions with alcohols. The epoxide was opened with regioselective attack at C-1 to give beta-galacto configured C-1 ethers. Using carbohydrates as nucleophiles, we synthesised a number of pseudodisaccharides. The epoxide was also regioselectively opened at C-1 with a sulfur nucleophile under basic conditions to give a beta-galacto configured C-1 thioether. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.04.032

文献信息

• Synthesis of carbadisaccharide mimics of galactofuranosides
  作者：Jens Frigell、Ian Cumpstey

  DOI：10.1016/j.tetlet.2009.06.115

  日期：2009.9

  A partially protected carbagalactofuranose was converted into a 1,2-anhydro derivative. This epoxide was opened with alcohol nucleophiles under Lewis acid catalysis to give beta-carbagalactofuranose pseudodisaccharides with excellent regioselectivity. (C) 2009 Elsevier Ltd. All rights reserved.