methyl 4,6-O-cyclohexylidene-2,3-di-O-benzyl-1-thio-α-D-mannopyranoside | 1236054-95-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4,6-O-cyclohexylidene-2,3-di-O-benzyl-1-thio-α-D-mannopyranoside
• CAS: 1236054-95-7
• 化学式: C₂₇H₃₄O₅S
• 分子量: 470.63
• InChiKey: DZUNRXOOTDJSAC-PUHDZGQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.32
• 重原子数：
  33.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  methyl 4,6-O-cyclohexylidene-2,3-di-O-benzyl-1-thio-α-D-mannopyranoside 、 benzyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside 在 2,6-二叔丁基-4-甲基吡啶 、 三氟甲烷磺酸甲酯 作用下， 以 对二甲苯 为溶剂， 反应 0.5h， 生成 benzyl 4,6-O-cyclohexylidene-2,3-di-O-benzyl-β-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside 、 benzyl 4,6-O-cyclohexylidene-2,3-di-O-benzyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Effects of frozen conditions on stereoselectivity and velocity of O-glycosylation reactions

  摘要：

  Rate acceleration of O-glycosylation had been observed in p-xylene under frozen conditions, when thioglycosides were activated by methyl trifluoromethane sulfonate. Curiously, significant perturbation of stereoselectivity was observed. Effects of various factors, such as solvent, concentration, anomeric configuration and protective groups of the donor, were systematically examined to clarify the mechanistic implications of stereoselectivity on glycosylation under frozen system. Our study revealed that the stereoselectivity was affected by concentration both in liquid as well as in frozen conditions, indicating that rate acceleration effect in frozen solvent was caused by highly concentrated environments. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.04.013
• 作为产物：
  描述：

  溴甲苯 、 methyl 4,6-O-cyclohexylidene-1-thio-α-D-mannopyranoside 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 以78%的产率得到methyl 4,6-O-cyclohexylidene-2,3-di-O-benzyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Effects of frozen conditions on stereoselectivity and velocity of O-glycosylation reactions

  摘要：

  Rate acceleration of O-glycosylation had been observed in p-xylene under frozen conditions, when thioglycosides were activated by methyl trifluoromethane sulfonate. Curiously, significant perturbation of stereoselectivity was observed. Effects of various factors, such as solvent, concentration, anomeric configuration and protective groups of the donor, were systematically examined to clarify the mechanistic implications of stereoselectivity on glycosylation under frozen system. Our study revealed that the stereoselectivity was affected by concentration both in liquid as well as in frozen conditions, indicating that rate acceleration effect in frozen solvent was caused by highly concentrated environments. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.04.013