Benzyl 2,3:4,6-di-O-isopropylidene-α-D-glucopyranoside | 117275-31-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: Benzyl 2,3:4,6-di-O-isopropylidene-α-D-glucopyranoside
• CAS: 117275-31-7
• 化学式: C₁₉H₂₆O₆
• 分子量: 350.412
• InChiKey: QNYVELBQGTXQGL-UUAJXVIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Benzyl 2,3:4,6-di-O-isopropylidene-α-D-glucopyranoside 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、172.37 kPa 条件下， 反应 48.0h， 生成 2,3:4,6-di-O-isopropylidene-D-glucopyranose
  参考文献：
  名称：

  Improved synthesis of 2,3:4,6-di-O-isopropylidene-d-glucopyranose and -d-galactopyranose

  摘要：

  2,3:4,6-Di-O-isopropylidene-D-glucopyranose and -D-galactopyranose acetals are conveniently prepared by hydrogenolysis of benzyl 2,3:4,6-di-O-isopropylidene-beta-D-glucopyranose and -beta-D-galactopyranose in almost quantitative yields in 3 h. This result is in contrast with the sluggish reaction observed (48 h) when the hydrogenolysis was carried out on either anomeric alpha,beta mixtures or on the corresponding a anomers. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00150-0
• 作为产物：
  描述：

  2-甲氧基丙烯 、 苄基Alpha-D-吡喃葡萄糖苷 在 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以68%的产率得到Benzyl 2,3:4,6-di-O-isopropylidene-α-D-glucopyranoside
  参考文献：
  名称：

  Improved synthesis of 2,3:4,6-di-O-isopropylidene-d-glucopyranose and -d-galactopyranose

  摘要：

  2,3:4,6-Di-O-isopropylidene-D-glucopyranose and -D-galactopyranose acetals are conveniently prepared by hydrogenolysis of benzyl 2,3:4,6-di-O-isopropylidene-beta-D-glucopyranose and -beta-D-galactopyranose in almost quantitative yields in 3 h. This result is in contrast with the sluggish reaction observed (48 h) when the hydrogenolysis was carried out on either anomeric alpha,beta mixtures or on the corresponding a anomers. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00150-0

文献信息

• From Sugars to Carbocycles. 3. Synthesis of Validatol and 4-epi-Validatol from Mannose and Glucose
  作者：Karsten Krohn、Guido Boerner、Stephan Gringard

  DOI：10.1021/jo00099a044

  日期：1994.10

  Validatol (4) and 4-epi-validatol (8) are synthesized from mannose and glucose, respectively. The key step in the synthesis of 4 is the base-induced intramolecular displacement reaction of the epoxy dithiane 14 to yield the six-membered carbocycle 15 exclusively.