methyl (phenyl 3-O-benzyl-1-thio-β-D-glucopyranosyluronate) | 1372659-96-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (phenyl 3-O-benzyl-1-thio-β-D-glucopyranosyluronate)
• CAS: 1372659-96-5
• 化学式: C₂₀H₂₂O₆S
• 分子量: 390.457
• InChiKey: DFDKXNJUYXVYNY-STEXWYFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.98
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  85.22
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl (phenyl 3-O-benzyl-1-thio-β-D-glucopyranosyluronate) 在 2,6-二甲基吡啶 、 二苯基亚砜 、 2,4,6-三叔丁基嘧啶 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 1.67h， 生成 methyl 2,3,4-tri-O-acetyl-6-O-(methyl 3-O-benzyl-2,4-O-di-tert-butylsilylene-β-D-glucopyranosyluronate)-α-D-glucopyranoside
  参考文献：
  名称：

  Strict Stereocontrol by 2,4-O-Di-tert-butylsilylene Group on β-Glucuronylations

  摘要：

  Strict beta-controlled glucuronylations without classical neighboring-group participation were achieved by the assistance of a 2,4-O-di-tert-butylsilylene group. Comparison of activation conditions and conformational analysis indicated that the strict beta-selectivity was achieved by steric hindrance of the 2,4-O-di-tert-butylsilylene group and not by complex glycosyl intermediates.

  DOI：

  10.1021/ol300634x
• 作为产物：
  描述：

  phenyl 2,4,6-tri-O-acetyl-3-O-benzyl-1-thio-β-D-glucopyranoside 在 甲醇 、 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 、 sodium methylate 作用下， 以 甲醇 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 methyl (phenyl 3-O-benzyl-1-thio-β-D-glucopyranosyluronate)
  参考文献：
  名称：

  Strict Stereocontrol by 2,4-O-Di-tert-butylsilylene Group on β-Glucuronylations

  摘要：

  Strict beta-controlled glucuronylations without classical neighboring-group participation were achieved by the assistance of a 2,4-O-di-tert-butylsilylene group. Comparison of activation conditions and conformational analysis indicated that the strict beta-selectivity was achieved by steric hindrance of the 2,4-O-di-tert-butylsilylene group and not by complex glycosyl intermediates.

  DOI：

  10.1021/ol300634x

文献信息

• Strict Stereocontrol by 2,4-<i>O</i>-Di-<i>tert</i>-butylsilylene Group on β-Glucuronylations
  作者：Takayuki Furukawa、Hiroshi Hinou、Shin-Ichiro Nishimura

  DOI：10.1021/ol300634x

  日期：2012.4.20

  Strict beta-controlled glucuronylations without classical neighboring-group participation were achieved by the assistance of a 2,4-O-di-tert-butylsilylene group. Comparison of activation conditions and conformational analysis indicated that the strict beta-selectivity was achieved by steric hindrance of the 2,4-O-di-tert-butylsilylene group and not by complex glycosyl intermediates.