1,2-anhydro-3,5,6-tri-O-benzyl-4a-carba-α-D-galactofuranose | 1187444-83-2

• 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: 1,2-anhydro-3,5,6-tri-O-benzyl-4a-carba-α-D-galactofuranose
• 英文别名: (1S,2S,3S,5S)-3-[(1S)-1,2-bis(phenylmethoxy)ethyl]-2-phenylmethoxy-6-oxabicyclo[3.1.0]hexane
• CAS: 1187444-83-2
• 化学式: C₂₈H₃₀O₄
• 分子量: 430.544
• InChiKey: WXAXOHIWOHBYRU-KLMIGJKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-anhydro-3,5,6-tri-O-benzyl-4a-carba-α-D-galactofuranose 在 三氟化硼乙醚 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 [(1S,2S,3S,5R)-3-[(1S)-1,2-bis(phenylmethoxy)ethyl]-5-[(2-methylpropan-2-yl)oxy]-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：

  3,4,6-三-O-苄基葡萄糖 在 盐酸 、 正丁基锂 、 Hoveyda-Grubbs catalyst second generation 、 草酰氯 、 偶氮二甲酸二异丙酯 、 palladium 10% on activated carbon 、 D(+)-10-樟脑磺酸 、 氢气 、 二甲基亚砜 、 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 6.0h， 生成 1,2-anhydro-3,5,6-tri-O-benzyl-4a-carba-α-D-galactofuranose
  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

• Carbasugar Analogues of Galactofuranosides: Pseudodisaccharide Mimics of Fragments of Mycobacterial Arabino­galactan
  作者：Jens Frigell、Jean A. Pearcey、Todd L. Lowary、Ian Cumpstey

  DOI：10.1002/ejoc.201001380

  日期：2011.3

  A partially protected carbasugar analogue of β-galactofuranose was converted into an α-galacto configured 1,2-epoxide, which was was opened by alcohols under Lewis acid catalysis with regioselectiv ...

  部分保护的 β-呋喃半乳糖类似物被转化为 α-半乳糖配置的 1,2-环氧化物，在路易斯酸催化下通过区域选择性的醇将其打开。
• 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.
• Carbasugar analogues of galactofuranosides: β-O-linked derivatives and towards β-S-linked derivatives
  作者：Jens Frigell、Lars Eriksson、Ian Cumpstey

  DOI：10.1016/j.carres.2011.04.032

  日期：2011.8

  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.