3,4,6-(tri-O-benzyl)-2-deoxy-1-(1'-oxocyclohexanyl)-β-D-glucopyranoside | 1294480-84-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,6-(tri-O-benzyl)-2-deoxy-1-(1'-oxocyclohexanyl)-β-D-glucopyranoside
• 英文别名: 2-[(2R,4R,5S,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]cyclohexan-1-one
• CAS: 1294480-84-4
• 化学式: C₃₃H₃₈O₅
• 分子量: 514.662
• InChiKey: BBZSVHHRBVDPCU-HIOWECNSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-[(2S,3S,4S,5R,6R)-3-(4-methylphenyl)sulfanyl-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]cyclohexan-1-one 在 W-2 Raney nickel 作用下， 以 四氢呋喃 为溶剂， 以51%的产率得到3,4,6-(tri-O-benzyl)-2-deoxy-1-(1'-oxocyclohexanyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Reduction of 2-Arylthio-β-C-D-Glucopyranosides with Different Functional Groups in the Lateral Chain

  摘要：

  [image omitted] 2-Arylthio--C-D-glucopyranosides with a carbonyl or methoxy group in the lateral chain (1 and 2) can be converted to the corresponding 2-deoxy--C-D-glucopyranosides (1a and 2a) using Raney Ni. Reduction of 2-arylthio--C-D-glucopyranosides bearing an ester, methoxy, CN, or C=C moiety in the side chain (3-6) using n-Bu3SnH in the presence of azobisisobutyronitrile (AIBN) provided the corresponding 2-deoxy--C-D-glucopyranosides (3a-6a) without reducing additional functional groups. The application of n-Bu3SnH and AIBN in reaction with 2-arylthio--C-D-glucopyranoside (7) containing a Me3Si group bonded to the carbonyl fragment (7) resulted in the reduction of both the 2-ArS and C=O groups.

  DOI：

  10.1080/00397911.2010.481738

文献信息

• Reduction of 2-Arylthio-<font>β</font>-<i>C</i>-<scp>D</scp>-Glucopyranosides with Different Functional Groups in the Lateral Chain
  作者：Mingming Han、Irina P. Smoliakova

  DOI：10.1080/00397911.2010.481738

  日期：2011.3.28

  [image omitted] 2-Arylthio--C-D-glucopyranosides with a carbonyl or methoxy group in the lateral chain (1 and 2) can be converted to the corresponding 2-deoxy--C-D-glucopyranosides (1a and 2a) using Raney Ni. Reduction of 2-arylthio--C-D-glucopyranosides bearing an ester, methoxy, CN, or C=C moiety in the side chain (3-6) using n-Bu3SnH in the presence of azobisisobutyronitrile (AIBN) provided the corresponding 2-deoxy--C-D-glucopyranosides (3a-6a) without reducing additional functional groups. The application of n-Bu3SnH and AIBN in reaction with 2-arylthio--C-D-glucopyranoside (7) containing a Me3Si group bonded to the carbonyl fragment (7) resulted in the reduction of both the 2-ArS and C=O groups.