methyl 2-O-methyl-4,6-O-(phenylmethylene)-β-D-galactopyranoside | 35780-85-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: methyl 2-O-methyl-4,6-O-(phenylmethylene)-β-D-galactopyranoside
• 英文别名: (4aR,6R,7R,8S,8aR)-6,7-dimethoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-ol
• CAS: 35780-85-9
• 化学式: C₁₅H₂₀O₆
• 分子量: 296.32
• InChiKey: CMABQYQMHIOHML-YGUXGGITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-O-methyl-4,6-O-(phenylmethylene)-β-D-galactopyranoside 在 吡啶 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 66.0h， 生成 (2R,3R,4R,5R,6R)-4-azido-2-(hydroxymethyl)-5,6-dimethoxyoxan-3-ol
  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：

  methyl 3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-2-O-methyl-β-D-galactopyranoside 在 4-甲基苯磺酸吡啶 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 7.5h， 生成 methyl 2-O-methyl-4,6-O-(phenylmethylene)-β-D-galactopyranoside
  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

• RAO, A. V. RAMA;DHAR, T. G. MURALI;GUJAR, M. K.;YADAV, J. S., INDIAN J. CHEM., 25,(1986) N 10, 999-1000
  作者：RAO, A. V. RAMA、DHAR, T. G. MURALI、GUJAR, M. K.、YADAV, J. S.

  DOI：——

  日期：——