methyl 3-amino-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)-3-N-<(trichloroacetamido)carbonyl>-β-D-gulopyranoside | 157068-65-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-amino-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)-3-N-<(trichloroacetamido)carbonyl>-β-D-gulopyranoside
• 英文别名: [(2S,3R,4S,6S)-2-[(2R,3R,4R,5R,6R)-5,6-dimethoxy-2-(phenylmethoxymethyl)-4-[(2,2,2-trichloroacetyl)carbamoylamino]oxan-3-yl]oxy-6-(phenylmethoxymethyl)-4-[(2,2,2-trifluoroacetyl)amino]oxan-3-yl] 2,2-dimethylpropanoate
• CAS: 157068-65-0
• 化学式: C₃₈H₄₇Cl₃F₃N₃O₁₂
• 分子量: 901.158
• InChiKey: SYDQXWGHMQWEHP-FPHYCXEFSA-N

物化性质

• 密度：
  1.39±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  59
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  178
• 氢给体数：
  3
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  methyl 3-amino-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)-3-N-<(trichloroacetamido)carbonyl>-β-D-gulopyranoside 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 甲醇 为溶剂， 反应 48.0h， 生成 methyl 3-N-(acetamidocarbonyl)-6-O-acetyl-3-amino-3-deoxy-4-<6'-O-acetyl-3',4'-dideoxy-2'-O-(2,2-dimethylpropionyl)-3'-(trifluoroacetamido)-β-D-glucopyranosyl>-2-O-methyl-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 在 N-碘代丁二酰亚胺 、 3 A molecular sieve 、 水 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 9.84h， 生成 methyl 3-amino-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)-3-N-<(trichloroacetamido)carbonyl>-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