octyl 3,4,6-tri-O-benzoyl-β-D-arabino-hexopyranosid-2-ulose | 562075-67-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: octyl 3,4,6-tri-O-benzoyl-β-D-arabino-hexopyranosid-2-ulose
• 英文别名: [(2R,3R,4S,6R)-3,4-dibenzoyloxy-6-octoxy-5-oxooxan-2-yl]methyl benzoate
• CAS: 562075-67-6
• 化学式: C₃₅H₃₈O₉
• 分子量: 602.681
• InChiKey: ATDDQAWHUGCTOT-JYYIKNSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  44
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  octyl 3,4,6-tri-O-benzoyl-β-D-arabino-hexopyranosid-2-ulose 在 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 反应 0.02h， 生成 octyl 3,4,6-tri-O-benzoyl-β-D-mannopyranoside
  参考文献：
  名称：

  manno- versus gluco-Selectivity in reductions of 2-keto-β-d-arabino-hexopyranosides

  摘要：

  Tri-sec-butylborohydrides (L- or K-Selectride) reduce the carbonyl group in acylated 2-keto-beta-D-arabino-hexopyranosides to beta-D-mannosides in an essentially stereospecific fashion, whereas borane reduction gives the 2-epimeric beta-D-glucosides with high preference. As preparative yields are in the 70-85% range, the ulosyl donor approach can thus be utilized for the straightforward construction of oligosaccharides containing either beta-D-Man or beta-D-Glc units. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00028-4
• 作为产物：
  描述：

  辛醇 、 3,4,6-tri-O-benzoyl-α-D-arabino-hexopyranosyl-2-ulose bromide 在 3 A molecular sieve 、 silver alumosilicate 作用下， 以 二氯甲烷 为溶剂， 反应 0.03h， 以84%的产率得到octyl 3,4,6-tri-O-benzoyl-β-D-arabino-hexopyranosid-2-ulose
  参考文献：
  名称：

  manno- versus gluco-Selectivity in reductions of 2-keto-β-d-arabino-hexopyranosides

  摘要：

  Tri-sec-butylborohydrides (L- or K-Selectride) reduce the carbonyl group in acylated 2-keto-beta-D-arabino-hexopyranosides to beta-D-mannosides in an essentially stereospecific fashion, whereas borane reduction gives the 2-epimeric beta-D-glucosides with high preference. As preparative yields are in the 70-85% range, the ulosyl donor approach can thus be utilized for the straightforward construction of oligosaccharides containing either beta-D-Man or beta-D-Glc units. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00028-4

文献信息

• manno- versus gluco-Selectivity in reductions of 2-keto-β-d-arabino-hexopyranosides
  作者：Frieder W. Lichtenthaler、Matthias Lergenmüller、Siegfried Peters、Zsolt Varga

  DOI：10.1016/s0957-4166(03)00028-4

  日期：2003.3

  Tri-sec-butylborohydrides (L- or K-Selectride) reduce the carbonyl group in acylated 2-keto-beta-D-arabino-hexopyranosides to beta-D-mannosides in an essentially stereospecific fashion, whereas borane reduction gives the 2-epimeric beta-D-glucosides with high preference. As preparative yields are in the 70-85% range, the ulosyl donor approach can thus be utilized for the straightforward construction of oligosaccharides containing either beta-D-Man or beta-D-Glc units. (C) 2003 Elsevier Science Ltd. All rights reserved.