methyl 2,3,6-tri-O-benzyl-4-O-methylthiomethyl-α-D-glucopyranoside | 1243310-65-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,6-tri-O-benzyl-4-O-methylthiomethyl-α-D-glucopyranoside
• CAS: 1243310-65-7
• 化学式: C₃₀H₃₆O₆S
• 分子量: 524.678
• InChiKey: GFYAZSARQQCIOI-RLXMVLCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.45
• 重原子数：
  37.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-羟乙基甲砜 、 methyl 2,3,6-tri-O-benzyl-4-O-methylthiomethyl-α-D-glucopyranoside 在 iodonium(di-γ-collidine) perchlorate 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以64%的产率得到methyl 2,3,6-tri-O-benzyl-4-O-2-(methylsulfonyl)ethoxymethyl-α-D-glucopyranoside
  参考文献：
  名称：

  The methylsulfonylethoxymethyl (Msem) as a hydroxyl protecting group in oligosaccharide synthesis

  摘要：

  The methylsulfonylethoxymethyl (Msem) is introduced as a base-labile, non-participating protecting group in carbohydrate chemistry. Conditions to introduce the Msem on primary and secondary alcohols are described. Removal of the Msem is best achieved using a catalytic amount of tetrabutylammonium fluoride (TBAF), with or without a nucleophilic scavenger. Applicability of the Msem group is illustrated in the assembly of an all 1,3-cis-linked mannotrioside. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.06.007
• 作为产物：
  描述：

  甲基2,3,6-三-O-苄基-ALPHA-D-吡喃葡萄糖苷 、 氯甲基甲硫醚 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 1.0h， 以73%的产率得到methyl 2,3,6-tri-O-benzyl-4-O-methylthiomethyl-α-D-glucopyranoside
  参考文献：
  名称：

  The methylsulfonylethoxymethyl (Msem) as a hydroxyl protecting group in oligosaccharide synthesis

  摘要：

  The methylsulfonylethoxymethyl (Msem) is introduced as a base-labile, non-participating protecting group in carbohydrate chemistry. Conditions to introduce the Msem on primary and secondary alcohols are described. Removal of the Msem is best achieved using a catalytic amount of tetrabutylammonium fluoride (TBAF), with or without a nucleophilic scavenger. Applicability of the Msem group is illustrated in the assembly of an all 1,3-cis-linked mannotrioside. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.06.007