(3S,4R)-5-<(triisopropylsilyl)oxy>-3,4-(isopropylidenedioxy)penta-2-(1,3-dioxolane) | 221154-61-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,4R)-5-<(triisopropylsilyl)oxy>-3,4-(isopropylidenedioxy)penta-2-(1,3-dioxolane)
• CAS: 221154-61-6
• 化学式: C₁₉H₃₈O₅Si
• 分子量: 374.593
• InChiKey: CBDYCOPESAQASY-SJORKVTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.46
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (3S,4R)-5-<(triisopropylsilyl)oxy>-3,4-(isopropylidenedioxy)penta-2-(1,3-dioxolane) 在 2,6-二甲基吡啶 、 四丁基氟化铵 、 四氯化碲 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 dimethyl (3S,4R)-3,4-isopropylidenedioxy-2-(1,3-dioxolane)-5-oxopentyl phosphate
  参考文献：
  名称：

  Synthesis of 1-Deoxy-d-xylulose and 1-Deoxy-d-xylulose-5-phosphate

  摘要：

  1-Deoxy-D-xylulose (4) and the corresponding 5-phosphate (5) are substrates for the first pathway-specific enzymes in the biosynthesis of thiamine diphosphate (vitamin B-1), pyridoxol phosphate (vitamin B-6), and the nonmevalonate family of isoprenoid compounds recently discovered in bacteria and plant chloroplasts. Both 4 and 5 were synthesized from commercially available (-)-2,3-O-isopropylidene-D-threitol (10). The protected tetraol was converted to (-)-3,4-O-isopropylidene-5-triisopropylsilyl-1-deoxy-D-xylulose (14) in four steps. Treatment of 14 with acetic acid gave 4 in an overall yield of 69%. The corresponding 5-phosphate was obtained by protection the carbonyl group in 14, removal of the triisopropylsilyl moiety, and treatment of the resulting alcohol with trimethyl phosphite/TeCl4, trimethylsilyl bromide, water, and HCl in successive steps to give 5 in 58% overall yield from 10.

  DOI：

  10.1021/jo981966k
• 作为产物：
  描述：

  (4R,5R)-(2,2-dimethyl-5-triisopropylsilanyloxymethyl-[1,3]dioxolan-4-yl)methanol 在 N-甲基吡咯烷酮 、 四丙基高钌酸铵 、 草酰氯 、 4 Angstroems MS 、 对甲苯磺酸 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 苯 为溶剂， 反应 10.75h， 生成 (3S,4R)-5-<(triisopropylsilyl)oxy>-3,4-(isopropylidenedioxy)penta-2-(1,3-dioxolane)
  参考文献：
  名称：

  Synthesis of 1-Deoxy-d-xylulose and 1-Deoxy-d-xylulose-5-phosphate

  摘要：

  1-Deoxy-D-xylulose (4) and the corresponding 5-phosphate (5) are substrates for the first pathway-specific enzymes in the biosynthesis of thiamine diphosphate (vitamin B-1), pyridoxol phosphate (vitamin B-6), and the nonmevalonate family of isoprenoid compounds recently discovered in bacteria and plant chloroplasts. Both 4 and 5 were synthesized from commercially available (-)-2,3-O-isopropylidene-D-threitol (10). The protected tetraol was converted to (-)-3,4-O-isopropylidene-5-triisopropylsilyl-1-deoxy-D-xylulose (14) in four steps. Treatment of 14 with acetic acid gave 4 in an overall yield of 69%. The corresponding 5-phosphate was obtained by protection the carbonyl group in 14, removal of the triisopropylsilyl moiety, and treatment of the resulting alcohol with trimethyl phosphite/TeCl4, trimethylsilyl bromide, water, and HCl in successive steps to give 5 in 58% overall yield from 10.

  DOI：

  10.1021/jo981966k