[(2R,3R,4S,5S,6S)-6-[[(3aS,5R,6R,7S,7aS)-6-acetyloxy-2-cyano-2-methyl-7-[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-5-yl]methoxy]-3,4,5-triacetyloxyoxan-2-yl]methyl acetate | 227306-93-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3R,4S,5S,6S)-6-[[(3aS,5R,6R,7S,7aS)-6-acetyloxy-2-cyano-2-methyl-7-[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-5-yl]methoxy]-3,4,5-triacetyloxyoxan-2-yl]methyl acetate
• CAS: 227306-93-6
• 化学式: C₃₉H₅₁NO₂₅
• 分子量: 933.826
• InChiKey: OQIKIIOHPKQGQK-SJBKACGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  65
• 可旋转键数：
  25
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  325
• 氢给体数：
  0
• 氢受体数：
  26

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5S,6S)-6-[[(3aS,5R,6R,7S,7aS)-6-acetyloxy-2-cyano-2-methyl-7-[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-5-yl]methoxy]-3,4,5-triacetyloxyoxan-2-yl]methyl acetate 在 吡啶 、 Cl⁽³⁾HO₄ 、 sodium methylate 作用下， 以 甲醇 、 硝基甲烷 、 苯 为溶剂， 反应 5.0h， 生成 methyl 6-O-(3,6-di-O-D-mannopyranosyl-α-D-mannopyranosyl)-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of highly branched oligomannosides

  摘要：

  Helferich glycosylation of 1,2-O-[(1-cyano)ethylidene]-beta-D-mannopyranos with acetobromomannose results in selective 3,6-bis-glycosylation of the acceptor. The peracetylated trisaccharide cyanoethylidene derivative is an efficient glycosyl donor, which is exemplified by preparation of a branched tetrasaccharide.

  DOI：

  10.1007/bf02495616
• 作为产物：
  描述：

  (3aS,5R,6S,7S,7aS)-6,7-dihydroxy-5-(hydroxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-2-carbonitrile 在 吡啶 、 4-二甲氨基吡啶 、 氰化汞 、 mercury dibromide 作用下， 以 乙腈 为溶剂， 反应 32.0h， 生成 [(2R,3R,4S,5S,6S)-6-[[(3aS,5R,6R,7S,7aS)-6-acetyloxy-2-cyano-2-methyl-7-[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-5-yl]methoxy]-3,4,5-triacetyloxyoxan-2-yl]methyl acetate
  参考文献：
  名称：

  Synthesis of highly branched oligomannosides

  摘要：

  Helferich glycosylation of 1,2-O-[(1-cyano)ethylidene]-beta-D-mannopyranos with acetobromomannose results in selective 3,6-bis-glycosylation of the acceptor. The peracetylated trisaccharide cyanoethylidene derivative is an efficient glycosyl donor, which is exemplified by preparation of a branched tetrasaccharide.

  DOI：

  10.1007/bf02495616

文献信息

• Backinowsky; Abronina; Kochetkov, Russian Journal of Bioorganic Chemistry, 1998, vol. 24, # 9, p. 635 - 640
  作者：Backinowsky、Abronina、Kochetkov、Grachev

  DOI：——

  日期：——