phenyl 3-azido-3,4-dideoxy-2-O-(2,2-dimethylpropionyl)-6-O-(phenylmethyl)-1-thio-β-D-glucopyranoside | 157068-60-5

• 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: phenyl 3-azido-3,4-dideoxy-2-O-(2,2-dimethylpropionyl)-6-O-(phenylmethyl)-1-thio-β-D-glucopyranoside
• 英文别名: [(2S,3R,4S,6S)-4-azido-6-(phenylmethoxymethyl)-2-phenylsulfanyloxan-3-yl] 2,2-dimethylpropanoate
• CAS: 157068-60-5
• 化学式: C₂₄H₂₉N₃O₄S
• 分子量: 455.578
• InChiKey: PFRAMRXXUZPNAK-UVUJQTEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  84.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  phenyl 3-azido-3,4-dideoxy-2-O-(2,2-dimethylpropionyl)-6-O-(phenylmethyl)-1-thio-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 3 A molecular sieve 、 水 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.67h， 生成 methyl 3-azido-3-deoxy-4-<3',4'-dideoxy-2'-O-(2,2-dimethylpropionyl)-6'-O-(phenylmethyl)-3'-(trifluoroacetamido)-β-D-glucopyranosyl>-2-O-methyl-6-O-(phenylmethyl)-β-D-gulopyranoside
  参考文献：
  名称：

  An Ezomycin Model Glycosylation

  摘要：

  A model glycosylation reaction for application to the synthesis of the ezomycin class of antibiotics is described. The ezoaminuroic thioglycoside donor 13, with a reduced and protected C-6 position and trifluoroacetamide at C-3, was prepared from the Cerny epoxide 7 by a nine-step procedure. The model D-pulo-pyranoside acceptor 20, which closely resembles an actual acceptor in the vicinity of the reacting axial hydroxyl, was synthesized from methyl beta-D-galactopyranoside 14. Glycosylation with N-iodosuccinimide/triflic acid as promoter gave the disaccharide 21 in 90% yield.

  DOI：

  10.1021/jo00096a022
• 作为产物：
  描述：

  溴甲苯 、 2,2-Dimethyl-propionic acid (2S,3R,4S,6S)-4-azido-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 phenyl 3-azido-3,4-dideoxy-2-O-(2,2-dimethylpropionyl)-6-O-(phenylmethyl)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  An Ezomycin Model Glycosylation

  摘要：

  A model glycosylation reaction for application to the synthesis of the ezomycin class of antibiotics is described. The ezoaminuroic thioglycoside donor 13, with a reduced and protected C-6 position and trifluoroacetamide at C-3, was prepared from the Cerny epoxide 7 by a nine-step procedure. The model D-pulo-pyranoside acceptor 20, which closely resembles an actual acceptor in the vicinity of the reacting axial hydroxyl, was synthesized from methyl beta-D-galactopyranoside 14. Glycosylation with N-iodosuccinimide/triflic acid as promoter gave the disaccharide 21 in 90% yield.

  DOI：

  10.1021/jo00096a022

文献信息

• An Ezomycin Model Glycosylation
  作者：Spencer Knapp、Carlos Jaramillo、Brett Freeman

  DOI：10.1021/jo00096a022

  日期：1994.8

  A model glycosylation reaction for application to the synthesis of the ezomycin class of antibiotics is described. The ezoaminuroic thioglycoside donor 13, with a reduced and protected C-6 position and trifluoroacetamide at C-3, was prepared from the Cerny epoxide 7 by a nine-step procedure. The model D-pulo-pyranoside acceptor 20, which closely resembles an actual acceptor in the vicinity of the reacting axial hydroxyl, was synthesized from methyl beta-D-galactopyranoside 14. Glycosylation with N-iodosuccinimide/triflic acid as promoter gave the disaccharide 21 in 90% yield.