1-O-[2-azido-3-O-(4-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2,4,5,6-tetra-O-benzyl-D-myo-inositol | 1334379-56-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-[2-azido-3-O-(4-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2,4,5,6-tetra-O-benzyl-D-myo-inositol
• 英文别名: (1R,2R,3R,4R,5S,6R)-3-[(2R,3R,4R,5S,6R)-3-azido-4-[(4-bromophenyl)methoxy]-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-5-(naphthalen-2-ylmethoxy)oxan-2-yl]oxy-2,4,5,6-tetrakis(phenylmethoxy)cyclohexan-1-ol
• CAS: 1334379-56-4
• 化学式: C₇₄H₇₆BrN₃O₁₀Si
• 分子量: 1275.42
• InChiKey: GUPKUXQNZLOVTP-TZZNYKAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.15
• 重原子数：
  89
• 可旋转键数：
  27
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1-O-[2-azido-3-O-(4-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2,4,5,6-tetra-O-benzyl-D-myo-inositol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以95%的产率得到1-O-[2-azido-3-O-(4-bromobenzyl)-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2,4,5,6-tetra-O-benzyl-D-myo-inositol
  参考文献：
  名称：

  Desymmetrization of 2,4,5,6-Tetra-O-benzyl-d-myo-inositol for the Synthesis of Mycothiol

  摘要：

  An efficient chemical synthesis of mycothiol Involving the regioselective ketopinyl desymmetrization of 2,4,5,6-tetrabenzylated D-myo-inositol as the key step Is described. Together with a highly alpha-stereoselective D-glucosaminylation, the whole procedure was accomplished in eight steps with an overall yield of 40%.

  DOI：

  10.1021/ol202218n
• 作为产物：
  描述：

  1-O-[2-azido-3-O-(4-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2,4,5,6-tetra-O-benzyl-3-O-(1S)-ketopinyl-D-myoinositol 在 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 以95%的产率得到1-O-[2-azido-3-O-(4-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2,4,5,6-tetra-O-benzyl-D-myo-inositol
  参考文献：
  名称：

  Desymmetrization of 2,4,5,6-Tetra-O-benzyl-d-myo-inositol for the Synthesis of Mycothiol

  摘要：

  An efficient chemical synthesis of mycothiol Involving the regioselective ketopinyl desymmetrization of 2,4,5,6-tetrabenzylated D-myo-inositol as the key step Is described. Together with a highly alpha-stereoselective D-glucosaminylation, the whole procedure was accomplished in eight steps with an overall yield of 40%.

  DOI：

  10.1021/ol202218n