methyl 3,4-di-O-benzyl-2,6-dideoxy-3-C-methyl-α-L-xylo-hexopyranosyl-(1->4)-2,3,6-trideoxy-α-D-erythro-hexopyranoside | 634909-32-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,4-di-O-benzyl-2,6-dideoxy-3-C-methyl-α-L-xylo-hexopyranosyl-(1->4)-2,3,6-trideoxy-α-D-erythro-hexopyranoside
• CAS: 634909-32-3
• 化学式: C₂₈H₃₈O₆
• 分子量: 470.606
• InChiKey: CGNMEZKBSSZEHH-FQZNFPKWSA-N

物化性质

• 沸点：
  556.4±50.0 °C(predicted)
• 密度：
  1.13±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.24
• 重原子数：
  34.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 3,4-di-O-benzyl-2,6-dideoxy-3-C-methyl-α-L-xylo-hexopyranosyl-(1->4)-2,3,6-trideoxy-α-D-erythro-hexopyranoside 在 sodium 作用下， 以 四氢呋喃 、 氨 为溶剂， 反应 0.5h， 以75%的产率得到methyl 2,6-dideoxy-3-C-methyl-α-L-xylo-hexopyranosyl-(1->4)-2,3,6-trideoxy-α-D-erythro-hexopyranoside
  参考文献：
  名称：

  Synthesis of the polyketomycin disaccharide

  摘要：

  The disaccharide portion of the anthracycline antibiotic polyketomycin consists of the trideoxy sugar D-amicetose attached to the methyl-branched sugar L-axenose. The polyketomycin disaccharide was synthesized from methyl 2,3,6-trideoxy-alpha-D-erythro-hexopyranoside (methyl alpha-D-amicetoside) and phenyl 3,4-di-O-benzyl-2,6-dideoxy-3-C-methyl-l-thio-alpha,beta-L-xylo-hexopyranoside. The key coupling step was carried out by N-bromosuccinimide activation of the thioglycoside and gave the desired alpha (1-->4) linked disaccharide exclusively in 71% yield, which was debenzylated by sodium and liquid ammonia. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.07.023
• 作为产物：
  描述：

  methyl 4-O-benzoyl-6-bromo-2,3,6-trideoxy-α-D-erythrohexopyranoside 在 sodium hydroxide 、 偶氮二异丁腈 、 三氟甲磺酸酐 、 三正丁基氢锡 作用下， 以 乙醇 、 二氯甲烷 、 水 、 苯 为溶剂， 反应 20.25h， 生成 methyl 3,4-di-O-benzyl-2,6-dideoxy-3-C-methyl-α-L-xylo-hexopyranosyl-(1->4)-2,3,6-trideoxy-α-D-erythro-hexopyranoside
  参考文献：
  名称：

  Synthesis of the polyketomycin disaccharide

  摘要：

  The disaccharide portion of the anthracycline antibiotic polyketomycin consists of the trideoxy sugar D-amicetose attached to the methyl-branched sugar L-axenose. The polyketomycin disaccharide was synthesized from methyl 2,3,6-trideoxy-alpha-D-erythro-hexopyranoside (methyl alpha-D-amicetoside) and phenyl 3,4-di-O-benzyl-2,6-dideoxy-3-C-methyl-l-thio-alpha,beta-L-xylo-hexopyranoside. The key coupling step was carried out by N-bromosuccinimide activation of the thioglycoside and gave the desired alpha (1-->4) linked disaccharide exclusively in 71% yield, which was debenzylated by sodium and liquid ammonia. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.07.023