(2S,4S)-4-((2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-pyrrolidine-1,2-dicarboxylic acid 2-allyl ester 1-(9H-fluoren-9-ylmethyl) ester | 911291-39-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,4S)-4-((2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-pyrrolidine-1,2-dicarboxylic acid 2-allyl ester 1-(9H-fluoren-9-ylmethyl) ester
• 英文别名: 1-O-(9H-fluoren-9-ylmethyl) 2-O-prop-2-enyl (2S,4S)-4-[(2R,3S,4R,5R,6R)-3-hydroxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxypyrrolidine-1,2-dicarboxylate
• CAS: 911291-39-9
• 化学式: C₅₀H₅₁NO₁₀
• 分子量: 825.956
• InChiKey: OHDHUKJLXDCGRQ-CRDNGQBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  61
• 可旋转键数：
  19
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  122
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2S,4S)-4-((2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-pyrrolidine-1,2-dicarboxylic acid 2-allyl ester 1-(9H-fluoren-9-ylmethyl) ester 在 哌啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以74%的产率得到4-O-(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-cis-4-hydroxy-L-proline allyl ester
  参考文献：
  名称：

  β-Glycosides of Hydroxyproline via an Umpolung Approach

  摘要：

  Reaction of 1,2-O-dibutylstannylene-3,4-6-tri-O-benzyl-beta-D-mannopyranose with N alpha-fluorenylmethoxycarbonyl-cis-4-trifluoromethanesulfonyloxyproline allyl ester led to formation of beta-mannoside of trans-4-hydroxyproline. Subsequent manipulation of the C2 hydroxy group gave rise to beta-D-Glc and beta-D-GlcNAc derivatives.

  DOI：

  10.1021/ol061424m
• 作为产物：
  描述：

  Nα-fluorenylmethoxycarbonyl-trans-4-hydroxy-L-proline allyl ester 在 吡啶 、 二正丁基氧化锡 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 24.0h， 生成 (2S,4S)-4-((2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-pyrrolidine-1,2-dicarboxylic acid 2-allyl ester 1-(9H-fluoren-9-ylmethyl) ester
  参考文献：
  名称：

  β-Glycosides of Hydroxyproline via an Umpolung Approach

  摘要：

  Reaction of 1,2-O-dibutylstannylene-3,4-6-tri-O-benzyl-beta-D-mannopyranose with N alpha-fluorenylmethoxycarbonyl-cis-4-trifluoromethanesulfonyloxyproline allyl ester led to formation of beta-mannoside of trans-4-hydroxyproline. Subsequent manipulation of the C2 hydroxy group gave rise to beta-D-Glc and beta-D-GlcNAc derivatives.

  DOI：

  10.1021/ol061424m

文献信息

• β-Glycosides of Hydroxyproline via an Umpolung Approach
  作者：Karl J. Shaffer、Carol M. Taylor

  DOI：10.1021/ol061424m

  日期：2006.8.1

  Reaction of 1,2-O-dibutylstannylene-3,4-6-tri-O-benzyl-beta-D-mannopyranose with N alpha-fluorenylmethoxycarbonyl-cis-4-trifluoromethanesulfonyloxyproline allyl ester led to formation of beta-mannoside of trans-4-hydroxyproline. Subsequent manipulation of the C2 hydroxy group gave rise to beta-D-Glc and beta-D-GlcNAc derivatives.