(S)-4-benzotriazol-1-yl-2-((9H-fluoren-9-ylmethoxy)carbonylamino)-4-oxo-butyric acid tert-butyl ester | 1006722-07-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-4-benzotriazol-1-yl-2-((9H-fluoren-9-ylmethoxy)carbonylamino)-4-oxo-butyric acid tert-butyl ester
• 英文别名: tert-butyl (2S)-4-(benzotriazol-1-yl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxobutanoate
• CAS: 1006722-07-1
• 化学式: C₂₉H₂₈N₄O₅
• 分子量: 512.565
• InChiKey: TUKVJZAINFMXGK-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-4-benzotriazol-1-yl-2-((9H-fluoren-9-ylmethoxy)carbonylamino)-4-oxo-butyric acid tert-butyl ester 、 2,3,4,6-四-O-叔戊酰基-beta-D-吡喃半乳糖胺 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以65%的产率得到[(2R,3S,4S,5R,6R)-3,4,5-tris(2,2-dimethylpropanoyloxy)-6-[[(3S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-[(2-methylpropan-2-yl)oxy]-4-oxobutanoyl]amino]oxan-2-yl]methyl 2,2-dimethylpropanoate
  参考文献：
  名称：

  Regioselective Syntheses of β-N-Linked Glycoaminoacids and Glycopeptides

  摘要：

  [GRAPHICS]Acylation of tetra-O-pivaloyl-beta-D-galactopyranosylamine 2 by readily available N- (Cbz or Fmoc-alpha-aminoacyl) benzotriazoles under microwave irradiation proceeded diastereoselectively to give beta-N-glycoaminoacids 3a-d, (3c+3c') (compound numbers written within brackets represent a racemate or a diastereomeric mixture; compound numbers without brackets represent a single enantiomer) (83-92%), and glycosylated asparagine building block 9 (65%). N-Cbz-Protected peptidoylbenzotriazoles 4a-c similarly afforded beta-N-glycodipeptides 5a-c (76-81%). Regiospecific beta-N-linkage formation was established by ID and 2D NMR techniques for 3b.

  DOI：

  10.1021/jo7018637
• 作为产物：
  描述：

  T406石油添加剂 、 芴甲氧羰基-L-天冬氨酸-1-叔丁酯 在 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 反应 1.33h， 以87%的产率得到(S)-4-benzotriazol-1-yl-2-((9H-fluoren-9-ylmethoxy)carbonylamino)-4-oxo-butyric acid tert-butyl ester
  参考文献：
  名称：

  Regioselective Syntheses of β-N-Linked Glycoaminoacids and Glycopeptides

  摘要：

  [GRAPHICS]Acylation of tetra-O-pivaloyl-beta-D-galactopyranosylamine 2 by readily available N- (Cbz or Fmoc-alpha-aminoacyl) benzotriazoles under microwave irradiation proceeded diastereoselectively to give beta-N-glycoaminoacids 3a-d, (3c+3c') (compound numbers written within brackets represent a racemate or a diastereomeric mixture; compound numbers without brackets represent a single enantiomer) (83-92%), and glycosylated asparagine building block 9 (65%). N-Cbz-Protected peptidoylbenzotriazoles 4a-c similarly afforded beta-N-glycodipeptides 5a-c (76-81%). Regiospecific beta-N-linkage formation was established by ID and 2D NMR techniques for 3b.

  DOI：

  10.1021/jo7018637

文献信息

• Regioselective Syntheses of β-<i>N</i>-Linked Glycoaminoacids and Glycopeptides
  作者：Alan R. Katritzky、Tamari Narindoshvili、Bogdan Draghici、Parul Angrish

  DOI：10.1021/jo7018637

  日期：2008.1.1

  [GRAPHICS]Acylation of tetra-O-pivaloyl-beta-D-galactopyranosylamine 2 by readily available N- (Cbz or Fmoc-alpha-aminoacyl) benzotriazoles under microwave irradiation proceeded diastereoselectively to give beta-N-glycoaminoacids 3a-d, (3c+3c') (compound numbers written within brackets represent a racemate or a diastereomeric mixture; compound numbers without brackets represent a single enantiomer) (83-92%), and glycosylated asparagine building block 9 (65%). N-Cbz-Protected peptidoylbenzotriazoles 4a-c similarly afforded beta-N-glycodipeptides 5a-c (76-81%). Regiospecific beta-N-linkage formation was established by ID and 2D NMR techniques for 3b.