[(2R,3S,4S,5R,6R)-3,4,5-tris(2,2-dimethylpropanoyloxy)-6-[[(2S)-2-[[(2S)-4-methylsulfanyl-2-(phenylmethoxycarbonylamino)butanoyl]amino]propanoyl]amino]oxan-2-yl]methyl 2,2-dimethylpropanoate | 1006722-23-1

• 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: [(2R,3S,4S,5R,6R)-3,4,5-tris(2,2-dimethylpropanoyloxy)-6-[[(2S)-2-[[(2S)-4-methylsulfanyl-2-(phenylmethoxycarbonylamino)butanoyl]amino]propanoyl]amino]oxan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 1006722-23-1
• 化学式: C₄₂H₆₅N₃O₁₃S
• 分子量: 852.056
• InChiKey: XRUNZWMOKIGQEC-DCHZKYOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  59
• 可旋转键数：
  24
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  236
• 氢给体数：
  3
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  benzyl N-{(S)-1-[(S)-2-benzotriazol-1-yl-1-methyl-2-oxoethylcarbamoyl]-3-methylsulfanylpropyl}carbamate 、 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 3.5h， 以81%的产率得到[(2R,3S,4S,5R,6R)-3,4,5-tris(2,2-dimethylpropanoyloxy)-6-[[(2S)-2-[[(2S)-4-methylsulfanyl-2-(phenylmethoxycarbonylamino)butanoyl]amino]propanoyl]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

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.