dimethyl(thexyl)silyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside | 947335-94-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dimethyl(thexyl)silyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside
• CAS: 947335-94-6
• 化学式: C₃₅H₄₈O₆Si
• 分子量: 592.848
• InChiKey: QPGVYAXDJZXSOJ-RUOAZZEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.12
• 重原子数：
  42.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  dimethyl(thexyl)silyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside 在 4 A molecular sieve 、 四丁基氟化铵 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 44.0h， 生成 2,3,4-tri-O-benzyl-6-O-(4-methylbenzyl)-D-glucopyranose
  参考文献：
  名称：

  Dichloro‐cyanoacetimidates as Glycosyl Donors

  摘要：

  Transformation of 1-O-unprotected glucose and galactose derivatives (1a-d) into O-glycosyl dichloro-cyanoacetimidates (2a-d) was performed with dichloro-cyanoacetonitrile in the presence of DBU as base. Reaction with different acceptors (3a-d) under TMSOTf catalysis afforded glycosides 4 in high yields. Competition experiments with O-glucopyranosyl trichloroacetimidate 10a, bearing a 4-tert-butylbenzyl group at 6-O, and O-glucopyranosyl dichloro-cyanoacetimidate 10b, bearing a 4-methylbenzyl group at 6-O, displayed similar reactivities for these two types of glycosyl donors.

  DOI：

  10.1080/07328300701410650
• 作为产物：
  描述：

  dimethyl(thexyl)silyl 6-O-acetyl-2,3,4-tri-O-benzyl-β-D-glucopyranoside 在 甲醇 、 sodium methylate 作用下， 反应 23.0h， 以91%的产率得到dimethyl(thexyl)silyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Dichloro‐cyanoacetimidates as Glycosyl Donors

  摘要：

  Transformation of 1-O-unprotected glucose and galactose derivatives (1a-d) into O-glycosyl dichloro-cyanoacetimidates (2a-d) was performed with dichloro-cyanoacetonitrile in the presence of DBU as base. Reaction with different acceptors (3a-d) under TMSOTf catalysis afforded glycosides 4 in high yields. Competition experiments with O-glucopyranosyl trichloroacetimidate 10a, bearing a 4-tert-butylbenzyl group at 6-O, and O-glucopyranosyl dichloro-cyanoacetimidate 10b, bearing a 4-methylbenzyl group at 6-O, displayed similar reactivities for these two types of glycosyl donors.

  DOI：

  10.1080/07328300701410650