methyl 2,6-dideoxy-3-C-methyl-α-L-xylo-hexopyranosyl-(1->4)-2,3,6-trideoxy-α-D-erythro-hexopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,6-dideoxy-3-C-methyl-α-L-xylo-hexopyranosyl-(1->4)-2,3,6-trideoxy-α-D-erythro-hexopyranoside
• 英文别名: (2S,3R,4R,6S)-6-[(2R,3S,6S)-6-methoxy-2-methyloxan-3-yl]oxy-2,4-dimethyloxane-3,4-diol
• 化学式: C₁₄H₂₆O₆
• 分子量: 290.357
• InChiKey: GYVJCWRMFJZNIM-LZRJYULZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  methyl 4-O-benzoyl-6-bromo-2,3,6-trideoxy-α-D-erythrohexopyranoside 在 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 氨 、 水 、 乙腈 、 苯 为溶剂， 反应 22.75h， 生成 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

文献信息

• Synthesis of the polyketomycin disaccharide
  作者：Douglas S. Micalizzi、J.Patrick Dougherty、Lincoln A. Noecker、Garry R. Smith、Robert M. Giuliano

  DOI：10.1016/j.tetasy.2003.07.023

  日期：2003.10

  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.