cholesteryl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranoside | 141693-03-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: cholesteryl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6S)-5-acetamido-3,4-diacetyloxy-6-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]oxan-2-yl]methyl acetate
• CAS: 141693-03-0
• 化学式: C₄₁H₆₅NO₉
• 分子量: 715.968
• InChiKey: UWSBGBSFGMGGNG-BCFDWXJXSA-N

物化性质

• 沸点：
  757.3±60.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  51
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  cholesteryl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranoside 在 甲醇 、 sodium methylate 作用下， 以82%的产率得到N-[(2S,3R,4R,5S,6R)-2-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
  参考文献：
  名称：

  Zemlyakov; Kur'yanov; Tsikalov, Russian Journal of Bioorganic Chemistry, 1998, vol. 24, # 6, p. 393 - 397

  摘要：

  DOI：
• 作为产物：
  描述：

  2-deoxy-2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranose 在 1H-1,2,4-三唑 、 三氟甲磺酸三甲基硅酯 、 双氧水 作用下， 以 硝基甲烷 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 cholesteryl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  New α-selective thermal glycosylation of acetyl-protected 2-acetamido-2-deoxy-β-d-glucopyranosyl diphenylphosphinate

  摘要：

  This paper describes new alpha-selective thermal glycosylation using acetyl-protected 2-acetamido-2-deoxy-beta-D-glucopyranosyl diphenylphosphinate (4) as a glycosyl donor. When the glycosylation of 4 with 1-hexanol was carried out under Various conditions, the conditions using trimethylsilyl trifluoromethanesulfonate as a promoter in nitromethane at reflux temperature were most suitable for the formation of the alpha anomer. The glycosylation of 4 with the other common alcohols gave corresponding alpha-glycosides in relatively high yields under the conditions. When cholesterol, a very steric hindered alcohol, was used as a glycosyl acceptor, alpha-glycoside was also produced predominantly. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00069-0

文献信息

• Zemlyakov; Kur'yanov; Sidorova, Russian Journal of Bioorganic Chemistry, 1998, vol. 24, # 8, p. 551 - 558
  作者：Zemlyakov、Kur'yanov、Sidorova、Chirva

  DOI：——

  日期：——
• Stereoselective thermal glycosylation of 2-deoxy-2-acetoamino-3,4,6-tri-O-acetyl-α-D-glucopyranosyl chloride
  作者：Mugio Nishizawa、Waka Shimomoto、Fumiko Momii、Hidetoshi Yamada

  DOI：10.1016/s0040-4039(00)74174-8

  日期：1992.3

  Thermal glycosylation of alcohols with 2-deoxy-2-acetoamino-3,4,6-tri-O-acetyl-glucopyranosyl chloride at relatively lower temperature gives rise to beta-glycosides selectively, whereas higher temperature favor to give alpha-glycosides.