methyl 3-azido-3-deoxy-2-O-methyl-6-O-(phenylmethyl)-β-D-gulopyranoside | 157068-63-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-azido-3-deoxy-2-O-methyl-6-O-(phenylmethyl)-β-D-gulopyranoside
• 英文别名: (2R,3R,4R,5R,6R)-4-azido-5,6-dimethoxy-2-(phenylmethoxymethyl)oxan-3-ol
• CAS: 157068-63-8
• 化学式: C₁₅H₂₁N₃O₅
• 分子量: 323.349
• InChiKey: BHNZHVJQPOOSRU-UXXRCYHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 3-azido-3-deoxy-2-O-methyl-6-O-(phenylmethyl)-β-D-gulopyranoside 在 N-碘代丁二酰亚胺 、 3 A molecular sieve 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.67h， 生成
  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：

  甲基-Β-D-吡喃半乳糖苷 在 吡啶 、 3 A molecular sieve 、 四丁基溴化铵 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 二正丁基氧化锡 、 对甲苯磺酸 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 、 苯 为溶剂， 反应 133.5h， 生成 methyl 3-azido-3-deoxy-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

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.