phenyl 2,6-O-benzyl-3,4,O-(butane-2,3-diyl)-1-thio-β-D-glucopyranoside | 943230-21-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,6-O-benzyl-3,4,O-(butane-2,3-diyl)-1-thio-β-D-glucopyranoside
• CAS: 943230-21-5
• 化学式: C₃₀H₃₄O₅S
• 分子量: 506.663
• InChiKey: JXVHXYFUOKBBCX-BZWUYPDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.87
• 重原子数：
  36.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  phenyl 2,6-O-benzyl-3,4,O-(butane-2,3-diyl)-1-thio-β-D-glucopyranoside 在 4 A molecular sieve 、 2,4,6-三叔丁基嘧啶 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 methyl 2,3,6-tri-O-benzyl-4-O-[2,6-di-O-benzyl-3,4-O-(butane-2,3-diyl)-β-D-glucopyranosyl]-α-D-glucopyranoside
  参考文献：
  名称：

  β-Selective glucosylation in the absence of neighboring group participation: influence of the 3,4-O-bisacetal protecting system

  摘要：

  A 3,4-O-bisacetal 2,6-di-O-benzyl protected thioglucoside is converted to the corresponding glucosyl triflate with 1-benzenesulfinyl piperidine and trifluoromethanesulfonic anhydride. The moderate to excellent beta-selectivity exhibited with this glucosyl triflate with a range of alcohols is generally higher than that observed with the more electronically disarmed corresponding 3,4-O-carbonate, for which a possible reason is advanced. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.128
• 作为产物：
  描述：

  phenyl 2,6-di-O-benzyl-3,4-di-O-(2,3-dimethoxybutane-2,3-diyl)-1-thio-β-D-glucopyranoside 在 盐酸 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 24.0h， 以70%的产率得到phenyl 2,6-O-benzyl-3,4,O-(butane-2,3-diyl)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  β-Selective glucosylation in the absence of neighboring group participation: influence of the 3,4-O-bisacetal protecting system

  摘要：

  A 3,4-O-bisacetal 2,6-di-O-benzyl protected thioglucoside is converted to the corresponding glucosyl triflate with 1-benzenesulfinyl piperidine and trifluoromethanesulfonic anhydride. The moderate to excellent beta-selectivity exhibited with this glucosyl triflate with a range of alcohols is generally higher than that observed with the more electronically disarmed corresponding 3,4-O-carbonate, for which a possible reason is advanced. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.128