methyl 3,5,6-tri-O-benzyl-4a-carba-β-D-galactofuranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside | 1187445-13-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,5,6-tri-O-benzyl-4a-carba-β-D-galactofuranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside
• CAS: 1187445-13-1
• 化学式: C₃₈H₄₈O₉
• 分子量: 648.794
• InChiKey: YMDDHOXAGTYIIR-NDUWUTGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.42
• 重原子数：
  47.0
• 可旋转键数：
  14.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  94.07
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  methyl 3,5,6-tri-O-benzyl-4a-carba-β-D-galactofuranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 以86%的产率得到methyl 2-O-acetyl-3,5,6-tri-O-benzyl-4a-carba-β-D-galactofuranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis of carbadisaccharide mimics of galactofuranosides

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2009.06.115
• 作为产物：
  描述：

  (2S,4S,5S,6R)-1,2,4-tri-O-benzyl-3-methyleneoct-7-ene-1,2,4,5,6-pentaol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 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 、 甲苯 为溶剂， 反应 69.5h， 生成 methyl 3,5,6-tri-O-benzyl-4a-carba-β-D-galactofuranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside
  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