chloromethyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranoside | 669714-20-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: chloromethyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranoside
• 英文别名: [(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[(2R,3R,4S,5R,6S)-4,5-diacetyloxy-2-(acetyloxymethyl)-6-(chloromethylsulfanyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate
• CAS: 669714-20-9
• 化学式: C₂₇H₃₇ClO₁₇S
• 分子量: 701.1
• InChiKey: ZHMDMVREOPAKIN-JIAHTRGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  46
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  237
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  chloromethyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranoside 在 sodium azide 作用下， 以 水 、 丙酮 为溶剂， 以90%的产率得到azidomethyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Glycosylthiomethyl Chloride:  A New Species for S-Neoglycoconjugate Synthesis. Synthesis of 1-N-Glycosylthiomethyl-1,2,3-triazoles

  摘要：

  Reaction of O-acyl-protected glycosylthiols with dichloromethane afforded readily glycosylthiomethyl chlorides, which gave with sodium azide the corresponding glycosylthiomethyl azides 17-22. Reaction of these azides with dicyclopentadiene as dipolarophile led to tandem 1,3-dipolar cycloaddition/retro-Diels-Alder reaction furnishing the parent 1-glycosylthiomethyl-1,2,3-triazoles 23-25. Reaction of azides with acetylene derivatives gave directly 1-glycosylthiomethyl-1,2,3-triazoles which are ring-substituted.

  DOI：

  10.1021/jo035300o
• 作为产物：
  描述：

  二氯甲烷 、 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-1-thio-β-D-glucopyranose 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以89%的产率得到chloromethyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Glycosylthiomethyl Chloride:  A New Species for S-Neoglycoconjugate Synthesis. Synthesis of 1-N-Glycosylthiomethyl-1,2,3-triazoles

  摘要：

  Reaction of O-acyl-protected glycosylthiols with dichloromethane afforded readily glycosylthiomethyl chlorides, which gave with sodium azide the corresponding glycosylthiomethyl azides 17-22. Reaction of these azides with dicyclopentadiene as dipolarophile led to tandem 1,3-dipolar cycloaddition/retro-Diels-Alder reaction furnishing the parent 1-glycosylthiomethyl-1,2,3-triazoles 23-25. Reaction of azides with acetylene derivatives gave directly 1-glycosylthiomethyl-1,2,3-triazoles which are ring-substituted.

  DOI：

  10.1021/jo035300o