[(2S,3S,4R,6S)-6-bromo-2-methyl-5-oxo-4-phenylmethoxyoxan-3-yl] benzoate | 194347-73-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(2S,3S,4R,6S)-6-bromo-2-methyl-5-oxo-4-phenylmethoxyoxan-3-yl] benzoate
• CAS: 194347-73-4
• 化学式: C₂₀H₁₉BrO₅
• 分子量: 419.272
• InChiKey: QXVRUDAKLKXNLB-ZQEOTTOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(2S,3S,4R,6S)-6-bromo-2-methyl-5-oxo-4-phenylmethoxyoxan-3-yl] benzoate 在 sodium tetrahydroborate 、 silver carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 isopropyl 4-O-benzoyl-3-O-benzyl-β-L-rhamnopyranoside
  参考文献：
  名称：

  Efficient generation of β-l-rhamnosidic linkages via the ulosyl bromide approach

  摘要：

  Practical protocols have been developed for the acquisition of ulosyl bromides of type III from L-rhamnose, i.e. 6-deoxy-alpha-L-arabino-2-ketohexosyl bromides 6-8. They have high potential as indirect beta-L-rhamnosyl donors, as they undergo beta-specific glycosidations under Koenigs-Knorr conditions, and carbonyl reductions of the resulting beta-L-ulosides proceed with high beta-L-rhamno selectivity. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01225-2
• 作为产物：
  描述：

  methyl 2-O-acetyl-4-O-benzoyl-3-O-benzyl-1-thio-α-L-rhamnopyranoside 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 lutidine 、 溴 作用下， 以 乙醇 为溶剂， 反应 5.33h， 生成 [(2S,3S,4R,6S)-6-bromo-2-methyl-5-oxo-4-phenylmethoxyoxan-3-yl] benzoate
  参考文献：
  名称：

  Efficient generation of β-l-rhamnosidic linkages via the ulosyl bromide approach

  摘要：

  Practical protocols have been developed for the acquisition of ulosyl bromides of type III from L-rhamnose, i.e. 6-deoxy-alpha-L-arabino-2-ketohexosyl bromides 6-8. They have high potential as indirect beta-L-rhamnosyl donors, as they undergo beta-specific glycosidations under Koenigs-Knorr conditions, and carbonyl reductions of the resulting beta-L-ulosides proceed with high beta-L-rhamno selectivity. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01225-2

文献信息

• Efficient generation of β-l-rhamnosidic linkages via the ulosyl bromide approach
  作者：Frieder W. Lichtenthaler、Thomas W. Metz

  DOI：10.1016/s0040-4039(97)01225-2

  日期：1997.8

  Practical protocols have been developed for the acquisition of ulosyl bromides of type III from L-rhamnose, i.e. 6-deoxy-alpha-L-arabino-2-ketohexosyl bromides 6-8. They have high potential as indirect beta-L-rhamnosyl donors, as they undergo beta-specific glycosidations under Koenigs-Knorr conditions, and carbonyl reductions of the resulting beta-L-ulosides proceed with high beta-L-rhamno selectivity. (C) 1997 Elsevier Science Ltd.