Fmoc-cis-Hyp-O-Allyl | 853245-42-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: Fmoc-cis-Hyp-O-Allyl
• 英文别名: 1-O-(9H-fluoren-9-ylmethyl) 2-O-prop-2-enyl (2S,4S)-4-hydroxypyrrolidine-1,2-dicarboxylate
• CAS: 853245-42-8
• 化学式: C₂₃H₂₃NO₅
• 分子量: 393.439
• InChiKey: YOPSSWWHIZQZBA-BTYIYWSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Fmoc-cis-Hyp-O-Allyl 在 吡啶 、 sodium azide 、 二正丁基氧化锡 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 28.0h， 生成 (2S,4R)-4-((2R,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-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
• 作为产物：
  描述：

  Nα-fluorenylmethoxycarbonyl-trans-4-hydroxy-L-proline allyl ester 在 sodium azide 、 dimethyl azodicarboxylate 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 28.0h， 生成 Fmoc-cis-Hyp-O-Allyl
  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

• A Solid-Phase Approach to the Phallotoxins:  Total Synthesis of [Ala⁷]-Phalloidin
  作者：Marc O. Anderson、Anang A. Shelat、R. Kiplin Guy

  DOI：10.1021/jo0503153

  日期：2005.6.1

  [GRAPHICS]Herein we report a solid-phase synthetic approach to [Ala(7)]-phalloidin (1). Prior syntheses of phallotoxins were carried out using solution-phase routes that required large scale and preclude library production. The route presented here consists of solution-phase preparation of key orthogonally protected amino acid building blocks, followed by a solid-phase peptide synthesis sequence, featuring two resin-bound macro-cyclization reactions. The final product mixture was composed of two atropisomeric compounds, one designated "natural" (1) and the other designated "non-natural" W). The structures of these species were modeled using restrained energy minimization with NMR-derived restraints.
• A Practical Solid-Phase Synthesis of Glu7-Phalloidin and Entry into Fluorescent F-Actin-Binding Reagents
  作者：Laura A. Schuresko、R. Scott Lokey

  DOI：10.1002/anie.200700017

  日期：2007.5.4
• 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.