6-O-α-D-galactopyranosyl-1,2:3,4-di-O-ispropylidene-α-D-galactopyranose | 40592-79-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-α-D-galactopyranosyl-1,2:3,4-di-O-ispropylidene-α-D-galactopyranose
• CAS: 40592-79-8
• 化学式: C₁₈H₃₀O₁₁
• 分子量: 422.43
• InChiKey: INRMYZZMSZQZFR-FPHFJNBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  145.53
• 氢给体数：
  4.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  6-O-α-D-galactopyranosyl-1,2:3,4-di-O-ispropylidene-α-D-galactopyranose 在 Dowex 50WX₈-100 、 水 作用下， 反应 12.0h， 生成 swietenose
  参考文献：
  名称：

  Synthesis of digalactosyl diacylglycerols and their structure–inhibitory activity on human lanosterol synthase

  摘要：

  Digalactosyl and monogalactocyl diacylglycerols (DGDG and MGDG), which were identified as anti-hyperlipemia active components in Colocasia esculenta (Taro), were synthesized. The inhibitory activity of DGDG, MGDG and related compounds on human lanosterol synthase was evaluated as anti-hyperlipemic activity. DGDG with two myristoyl groups at both sn-1 and sn-2 positions and with an oleoyl group at the sn-1 position showed the most potent activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.10.013
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 在 palladium on activated charcoal 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以96%的产率得到6-O-α-D-galactopyranosyl-1,2:3,4-di-O-ispropylidene-α-D-galactopyranose
  参考文献：
  名称：

  Application of the imidate procedure to α-d-galactosyltion

  摘要：

  DOI：

  10.1016/s0008-6215(00)81040-x

文献信息

• Glycosylation Using Unprotected Alkynyl Donors
  作者：Sreeman K. Mamidyala、M.G. Finn

  DOI：10.1021/jo901857x

  日期：2009.11.6

  Gold(III) activation of unprotected propargyl glycosyl donors has been shown to be effective for the synthesis of saccharides. Terminal propargyl glycosides of glucose, galactose, and mannose required heating at reflux in acetonitrile with 5% AuCl(3) for reaction with various primary alcohol acceptors, the latter used in 10-fold molar excess relative to donor. Donors containing the 2-butynyl group were more reactive, giving good yields of glycoside products at lower temperatures Secondary alcohols could also be used but with diminished efficiency. The propargylic family of donors is especially convenient because they can be easily prepared on large scale by Fischer glycosylation and stored indefinitely before chemoselective activation by the catalyst.