benzyl 2-acetamido-2,3,4,6-tetradeoxy-α-L-threo-hex-3-enopyranoside | 174151-46-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: benzyl 2-acetamido-2,3,4,6-tetradeoxy-α-L-threo-hex-3-enopyranoside
• 英文别名: N-[(2R,3R,6S)-6-methyl-2-phenylmethoxy-3,6-dihydro-2H-pyran-3-yl]acetamide
• CAS: 174151-46-3
• 化学式: C₁₅H₁₉NO₃
• 分子量: 261.321
• InChiKey: ONUAJPJEWLFBQE-NILFDRSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl 2-acetamido-2,3,4,6-tetradeoxy-α-L-threo-hex-3-enopyranoside 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到benzyl 2-acetamido-3,4-anhydro-2,6-dideoxy-α-L-talopyranoside
  参考文献：
  名称：

  关于2-乙酰氨基-3,4-脱水糖的环氧乙烷开环反应和衍生的醇的转化的观察

  摘要：

  描述了一种制备2，4-和2，3-二乙酰氨基-2，4，6-和2，3，6-三苯氧基吡喃糖的1-对映体的新颖方法。讨论了影响环氧化物开环和取代的空间过程的因素。

  DOI：

  10.1016/s0957-4166(00)00452-3
• 作为产物：
  描述：

  benzyl 2,3,4,6-tetradeoxy-2-trichloroacetamido-α-L-threo-hex-3-enopyranoside 在 吡啶 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 benzyl 2-acetamido-2,3,4,6-tetradeoxy-α-L-threo-hex-3-enopyranoside
  参考文献：
  名称：

  The synthesis of derivatives of 2,4-diamino-2,4,6-trideoxy-d-gulo- and l-altro-hexopyranoses

  摘要：

  Syntheses of two derivatives of two 2,4-diamino-2,4,6-trideoxyhexoses having the D-gulo (16) and L-altro (29) configuration have been described. Derivative 16 was obtained by two routes starting from benzyl 2-benzyloxycarbonylamino-2-deoxy-alpha-D-glucopyranoside. Derivative 29 was obtained from 3,4-di-O-acetyl-L-rhamnal in a 10-step reaction sequence.

  DOI：

  10.1016/0008-6215(95)00291-x

文献信息

• Observations on the oxirane ring opening reactions of a 2-acetamido-3,4-anhydro sugar and on the inversion of the derived alcohols
  作者：Anna Banaszek、Bożena Janisz

  DOI：10.1016/s0957-4166(00)00452-3

  日期：2000.12

  A novel methodology for the preparation of l-enantiomers of 2,4- and 2,3-diacetamido-2,4,6- and 2,3,6-trideoxy-pyranoses is described. Factors influencing both the steric course of the epoxide ring opening and substitution are discussed.

  描述了一种制备2，4-和2，3-二乙酰氨基-2，4，6-和2，3，6-三苯氧基吡喃糖的1-对映体的新颖方法。讨论了影响环氧化物开环和取代的空间过程的因素。
• The synthesis of derivatives of 2,4-diamino-2,4,6-trideoxy-d-gulo- and l-altro-hexopyranoses
  作者：Anna Banaszek、Zbigniew Pakulski、Aleksander Zamojski

  DOI：10.1016/0008-6215(95)00291-x

  日期：1995.12

  Syntheses of two derivatives of two 2,4-diamino-2,4,6-trideoxyhexoses having the D-gulo (16) and L-altro (29) configuration have been described. Derivative 16 was obtained by two routes starting from benzyl 2-benzyloxycarbonylamino-2-deoxy-alpha-D-glucopyranoside. Derivative 29 was obtained from 3,4-di-O-acetyl-L-rhamnal in a 10-step reaction sequence.