4,5-O-(1',2'-dimethoxycyclohexane-1',2'-diyl)-1,2-O-isopropylidene-3-O-methyl-D-chiro-inositol | 434335-31-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,5-O-(1',2'-dimethoxycyclohexane-1',2'-diyl)-1,2-O-isopropylidene-3-O-methyl-D-chiro-inositol
• 英文别名: (3aR,4R,4aS,5aS,9aS,10aS,11S,11aS)-4,5a,9a-trimethoxy-2,2-dimethyl-3a,4,4a,6,7,8,9,10a,11,11a-decahydro-[1,3]dioxolo[4,5-b]oxanthren-11-ol
• CAS: 434335-31-6
• 化学式: C₁₈H₃₀O₈
• 分子量: 374.431
• InChiKey: RXYRKYDATZLQLW-ZFLSTCQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  84.8
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4,5-O-(1',2'-dimethoxycyclohexane-1',2'-diyl)-1,2-O-isopropylidene-3-O-methyl-D-chiro-inositol 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 水 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.67h， 生成 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl-α(1->6)-3-O-methyl-D-chiro-inositol
  参考文献：
  名称：

  Synthesis and Structure of 1-D-6-O-(2-Amino-2-deoxy-α- and -β-D-gluco- and -galactopyranosyl)-3-O-methyl-D-chiro-inositol

  摘要：

  A convenient preparative synthesis of 1-D-6-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-3-O-methyl-chiro-inositol), 1-D-6-O-(2-amino-2-deoxy-beta-D-glucopyranosyl)-3-O-methyl- chiro-inositol (1b), I-D-6-O-(2-amino-2-deoxy-alpha-D-galactopyranosyl)-3-O-methyl-chiro-inositol (IIb), and 1-D-6-O-(2-amino-2-deoxy-beta-D-galactopyranosyl)-3-O-methyl-chiro-ino- sitol (IIb) from 3-O-methyl-D-chiro-inositol (pinitol) as starting material is reported. These compounds contain some of the basic structural motifs proposed for insulin mediators, The three-dimensional structures of these compounds have been determined by NMR spectroscopy and molecular dynamics simulations.

  DOI：

  10.1002/1099-0690(200203)2002:5<889::aid-ejoc889>3.0.co;2-3
• 作为产物：
  描述：

  D-松醇 在 D(+)-10-樟脑磺酸 、 对甲苯磺酸 、 原甲酸三甲酯 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 25.0h， 生成 4,5-O-(1',2'-dimethoxycyclohexane-1',2'-diyl)-1,2-O-isopropylidene-3-O-methyl-D-chiro-inositol
  参考文献：
  名称：

  Synthesis and Structure of 1-D-6-O-(2-Amino-2-deoxy-α- and -β-D-gluco- and -galactopyranosyl)-3-O-methyl-D-chiro-inositol

  摘要：

  A convenient preparative synthesis of 1-D-6-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-3-O-methyl-chiro-inositol), 1-D-6-O-(2-amino-2-deoxy-beta-D-glucopyranosyl)-3-O-methyl- chiro-inositol (1b), I-D-6-O-(2-amino-2-deoxy-alpha-D-galactopyranosyl)-3-O-methyl-chiro-inositol (IIb), and 1-D-6-O-(2-amino-2-deoxy-beta-D-galactopyranosyl)-3-O-methyl-chiro-ino- sitol (IIb) from 3-O-methyl-D-chiro-inositol (pinitol) as starting material is reported. These compounds contain some of the basic structural motifs proposed for insulin mediators, The three-dimensional structures of these compounds have been determined by NMR spectroscopy and molecular dynamics simulations.

  DOI：

  10.1002/1099-0690(200203)2002:5<889::aid-ejoc889>3.0.co;2-3