2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl diphenylphosphinate | 297132-68-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl diphenylphosphinate
• 英文别名: [(2R,3S,4R,5R,6S)-5-acetamido-3,4-diacetyloxy-6-diphenylphosphoryloxyoxan-2-yl]methyl acetate
• CAS: 297132-68-4
• 化学式: C₂₆H₃₀NO₁₀P
• 分子量: 547.499
• InChiKey: JQCDBUUVRRBLDP-SDVOOXDOSA-N

物化性质

• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  144
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  胆固醇 、 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl diphenylphosphinate 在 三氟甲磺酸三甲基硅酯 作用下， 以 硝基甲烷 为溶剂， 反应 2.0h， 以28%的产率得到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
• 作为产物：
  描述：

  P,P-二(3,5-二甲基苯基)-N,N-二乙基亚膦酰胺 在 1H-1,2,4-三唑 、 双氧水 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 生成 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl diphenylphosphinate
  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

• New α-selective thermal glycosylation of acetyl-protected 2-acetamido-2-deoxy-β-d-glucopyranosyl diphenylphosphinate
  作者：Jun-ichi Kadokawa、Takeshi Nagaoka、Jun Ebana、Hideyuki Tagaya、Koji Chiba

  DOI：10.1016/s0008-6215(00)00069-0

  日期：2000.7

  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.