methyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside | 84635-57-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6S)-5-acetamido-3,4-diacetyloxy-6-methylsulfanyloxan-2-yl]methyl acetate
• CAS: 84635-57-4
• 化学式: C₁₅H₂₃NO₈S
• 分子量: 377.416
• InChiKey: PKJYXAFUZVFJIM-RYPNDVFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  143
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  乙酰氯 、 methyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside 在 N,N-二异丙基乙胺 作用下， 以91%的产率得到[(2R,3S,4R,5R,6S)-3,4-diacetyloxy-5-(diacetylamino)-6-methylsulfanyloxan-2-yl]methyl acetate
  参考文献：
  名称：

  N,N-Diacetyl-Glucosamine and -Galactosamine Derivatives as Glycosyl Donors

  摘要：

  N-Acetyl-glucosamine and N-acetyl-galactosamine were converted into the O-acetyl protected 1-methylthio-derivatives 1A,B which were then transformed into N,N-diacetyl derivatives 2A and 2B, respectively. Activation of 2A,B with DMTST afforded good glycosyl donors for the generation of P-linkages: thus, reaction with accepters 3a,b gave oligosaccharides 4Aa and 4Ba in high and 4Ab and 4Bb in good yields. Mono-N-deacetylation could be performed with NaOMe/MeOH in quantitative yield, thus concluding a convenient procedure for the formation of beta-linked GlcNAc and GalNAc glycosides.

  DOI：

  10.1016/00404-0399(50)14068-
• 作为产物：
  描述：

  1-bromo-2-acetylamino-3,4,6-triacetoxy-2-deoxyglucose 在 sodium acetate 作用下， 以 丙酮 为溶剂， 反应 18.0h， 生成 methyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  A Through-process for the Preparation of Methyl Per-O-acetyl 1-Thio-glycosides from Aldoses

  摘要：

  d-葡萄糖、d-半乳糖、d-甘露糖、d-木糖、l-阿拉伯糖、l-岩藻糖、l-鼠李糖、麦芽糖、纤维二糖、乳糖、d-葡萄糖胺、d-半乳糖胺和d-甘露糖胺通过一个反应器经过三步（溴乙酰化、甲硫化和乙酰化）转化为相应的甲基全乙酰化1-硫代糖呋喃糖苷。

  DOI：

  10.1246/bcsj.55.3667

文献信息

• A Through-process for the Preparation of Methyl Per-<i>O</i>-acetyl 1-Thio-glycosides from Aldoses
  作者：Shinkiti Koto、Toyosaku Yoshida、Kazuhiro Takenaka、Shonosuke Zen

  DOI：10.1246/bcsj.55.3667

  日期：1982.11

  d-Glucose, d-galactose, d-mannose, d-xylose, l-arabinose, l-fucose, l-rhamnose, maltose, cellobiose, lactose, d-glucosamine, d-galactosamine, and d-mannosamine were converted into the corresponding methyl per-O-acetyl 1-thioglycopyranosides by way of a three-step (acetobromination, methylthioation, and acetylation) through-process in a single vessel.

  d-葡萄糖、d-半乳糖、d-甘露糖、d-木糖、l-阿拉伯糖、l-岩藻糖、l-鼠李糖、麦芽糖、纤维二糖、乳糖、d-葡萄糖胺、d-半乳糖胺和d-甘露糖胺通过一个反应器经过三步（溴乙酰化、甲硫化和乙酰化）转化为相应的甲基全乙酰化1-硫代糖呋喃糖苷。
• N,N-Diacetyl-Glucosamine and -Galactosamine Derivatives as Glycosyl Donors
  作者：J Castro-Palomino

  DOI：10.1016/00404-0399(50)14068-

  日期：1995.9.18

  N-Acetyl-glucosamine and N-acetyl-galactosamine were converted into the O-acetyl protected 1-methylthio-derivatives 1A,B which were then transformed into N,N-diacetyl derivatives 2A and 2B, respectively. Activation of 2A,B with DMTST afforded good glycosyl donors for the generation of P-linkages: thus, reaction with accepters 3a,b gave oligosaccharides 4Aa and 4Ba in high and 4Ab and 4Bb in good yields. Mono-N-deacetylation could be performed with NaOMe/MeOH in quantitative yield, thus concluding a convenient procedure for the formation of beta-linked GlcNAc and GalNAc glycosides.