azidomethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranoside | 669714-29-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: azidomethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[(2R,3R,4S,5R,6S)-4,5-diacetyloxy-2-(acetyloxymethyl)-6-(azidomethylsulfanyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate
• CAS: 669714-29-8
• 化学式: C₂₇H₃₇N₃O₁₇S
• 分子量: 707.667
• InChiKey: CPWIFOFRLOMYIE-OTEFYFLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.61
• 重原子数：
  48.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  260.55
• 氢给体数：
  0.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  (S)-2-((R)-2-Benzyloxycarbonylamino-4-thiocarboxy-butyrylamino)-propionic acid benzyl ester 、 azidomethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranoside 在 2,6-二甲基吡啶 作用下， 以 氯仿 为溶剂， 以65%的产率得到benzyl (2S)-2-[[(2R)-5-[[(2S,3R,4S,5R,6R)-3,4-diacetyloxy-6-(acetyloxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]sulfanylmethylamino]-5-oxo-2-(phenylmethoxycarbonylamino)pentanoyl]amino]propanoate
  参考文献：
  名称：

  Synthesis of Novel S-Neoglycopeptides from Glycosylthiomethyl Derivatives

  摘要：

  Reaction of glycosylthiomethyl azides with amino acid and peptide derivatives containing aspartate and glutamate thio acids gave the corresponding glycosylthiomethyl amides in excellent yields. Another type of neoglycopeptides was obtained via reaction of glycosylthiomethyl bromide with cysteine and homocysteine containing peptide derivatives, thus affording the corresponding S-(glycosylthiomethyl) peptides.

  DOI：

  10.1021/ol036186z
• 作为产物：
  描述：

  chloromethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(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84%的产率得到azidomethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(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