3,5,6-tri-O-benzyl-1-O-ethyl-4a-carba-β-D-galactofuranose | 1187444-98-9

• 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: 3,5,6-tri-O-benzyl-1-O-ethyl-4a-carba-β-D-galactofuranose
• 英文别名: (1S,2S,3S,5R)-3-[(1S)-1,2-bis(phenylmethoxy)ethyl]-5-ethoxy-2-phenylmethoxycyclopentan-1-ol
• CAS: 1187444-98-9
• 化学式: C₃₀H₃₆O₅
• 分子量: 476.613
• InChiKey: BMDVJMPAGHGPGW-CDTAUBPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  溴乙烷 、 3,5,6-tri-O-benzyl-1-O-ethyl-4a-carba-β-D-galactofuranose 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 4.0h， 以46%的产率得到3,5,6-tri-O-benzyl-1,2-di-O-ethyl-4a-carba-β-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
• 作为产物：
  描述：

  (2R,3R,4S,5S,6R)-1,2,4-tri-O-benzyl-5,6-O-isopropylidene-1,2,3,4,5,6-hexahydroxyoct-7-ene 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 、 三氟化硼乙醚 、 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 24.0h， 生成 3,5,6-tri-O-benzyl-1-O-ethyl-4a-carba-β-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

• 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.