3,4,5,7-tetra-O-benzyl-1-C-methanenitro-α-D-gluco-heptulopyranose | 189681-06-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,5,7-tetra-O-benzyl-1-C-methanenitro-α-D-gluco-heptulopyranose
• 英文别名: (2S,3R,4S,5R,6R)-2-(nitromethyl)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-ol
• CAS: 189681-06-9
• 化学式: C₃₅H₃₇NO₈
• 分子量: 599.681
• InChiKey: NJKLOOCTPCXDBV-KJQSSVQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  44
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,4,5,7-tetra-O-benzyl-1-C-methanenitro-α-D-gluco-heptulopyranose 在 三乙基硅烷 、 三氟化硼 、 三正丁基氢锡 、 L-Selectride 、 三乙胺 、 1,1'-偶氮(氰基环己烷) 作用下， 以 甲苯 、 乙腈 为溶剂， 生成 1,6-anhydro-3,4-dideoxy-4-C-(3,4,5,7-tetra-O-benzyl-2,6-anhydro-1-deoxy-α-D-gluco-2-heptulopyranos-1-yl)-D-glucopyranose
  参考文献：
  名称：

  C-Disaccharides I. Stereoselective approach to β-(1–4)-3-deoxy-C-disaccharides from levoglucosenone

  摘要：

  beta -(1-4)C-Disaccharides have been synthesized in four steps by stereoselective base catalyzed Michael addition reaction of glucosyl nitromethane to the chiral synthon, levoglucosenone followed by radical removal of the nitro group with tributyltinhydride. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00327-4
• 作为产物：
  描述：

  2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol 在 N-碘代丁二酰亚胺 、 sodium nitrite 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 3,4,5,7-tetra-O-benzyl-1-C-methanenitro-α-D-gluco-heptulopyranose
  参考文献：
  名称：

  C-Disaccharides I. Stereoselective approach to β-(1–4)-3-deoxy-C-disaccharides from levoglucosenone

  摘要：

  beta -(1-4)C-Disaccharides have been synthesized in four steps by stereoselective base catalyzed Michael addition reaction of glucosyl nitromethane to the chiral synthon, levoglucosenone followed by radical removal of the nitro group with tributyltinhydride. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00327-4

文献信息

• C-Disaccharides I. Stereoselective approach to β-(1–4)-3-deoxy-C-disaccharides from levoglucosenone
  作者：Zbigniew J. Witczak、Renu Chhabra、Joanna Chojnacki

  DOI：10.1016/s0040-4039(97)00327-4

  日期：1997.3

  beta -(1-4)C-Disaccharides have been synthesized in four steps by stereoselective base catalyzed Michael addition reaction of glucosyl nitromethane to the chiral synthon, levoglucosenone followed by radical removal of the nitro group with tributyltinhydride. (C) 1997 Elsevier Science Ltd.