1,2-di-O-acetyl-3,5,6-tri-O-benzyl-4a-carba-β-D-xylohex-4(4a)-enofuranose | 1005004-07-8

• 分子结构分类: 有机化合物
• 英文名称: 1,2-di-O-acetyl-3,5,6-tri-O-benzyl-4a-carba-β-D-xylohex-4(4a)-enofuranose
• 英文别名: [(1R,4S,5S)-5-acetyloxy-3-[(1S)-1,2-bis(phenylmethoxy)ethyl]-4-phenylmethoxycyclopent-2-en-1-yl] acetate
• CAS: 1005004-07-8
• 化学式: C₃₂H₃₄O₇
• 分子量: 530.618
• InChiKey: QCUAGJDJDGBZJA-ZRTHHSRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  39
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,2-di-O-acetyl-3,5,6-tri-O-benzyl-4a-carba-β-D-xylohex-4(4a)-enofuranose 在 偶氮二甲酸二异丙酯 、 palladium 10% on activated carbon 、 三氟化硼乙醚 、 氢气 、 sodium methylate 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 24.0h， 生成 2-O-acetyl-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
• 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 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 盐酸 、 正丁基锂 、 草酰氯 、 二甲基亚砜 作用下， 以 吡啶 、 正己烷 、 二氯甲烷 、 水 、 溶剂黄146 、 甲苯 为溶剂， 反应 69.0h， 生成 1,2-di-O-acetyl-3,5,6-tri-O-benzyl-4a-carba-β-D-xylohex-4(4a)-enofuranose
  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

• First synthesis of 4a-carba-β-d-galactofuranose
  作者：Jens Frigell、Ian Cumpstey

  DOI：10.1016/j.tetlet.2007.10.138

  日期：2007.12

  The synthesis of 4a-carba-β-d-galactofuranose is described starting from diacetone glucose. The key ring-closure step was carried out by metathesis to form a cyclopentene. Catalytic hydrogenation of the CC double bond gave the galacto configured saturated carbahexofuranose with excellent diastereoselectivity.

  描述了从双丙酮葡萄糖开始的4a-氨基甲酸酯-β-d-半乳糖呋喃糖的合成。通过复分解进行关键环闭合步骤以形成环戊烯。CC双键的催化加氢得到具有出色的非对映选择性的半乳糖构型的饱和呋喃呋喃呋喃糖。