5-C-benzoyloxymethyl-3,5-dideoxy-1,2-O-isopropylidene-β-D-erythro-hexulopyranose | 395666-10-1

• 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: 5-C-benzoyloxymethyl-3,5-dideoxy-1,2-O-isopropylidene-β-D-erythro-hexulopyranose
• 英文别名: [(5R,7S,8S)-7-hydroxy-2,2-dimethyl-1,3,10-trioxaspiro[4.5]decan-8-yl]methyl benzoate
• CAS: 395666-10-1
• 化学式: C₁₇H₂₂O₆
• 分子量: 322.358
• InChiKey: JXJLHTHHZKCVTB-JKIFEVAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-C-benzoyloxymethyl-3,5-dideoxy-1,2-O-isopropylidene-β-D-erythro-hexulopyranose 在 sodium methylate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 23.0h， 生成 3,5-dideoxy-5-C-hydroxymethyl-1,2-O-isopropylidene-β-D-threo-hexulopyranose
  参考文献：
  名称：

  SYNTHESIS OF BRANCHED-CHAIN HEXULOSE DERIVATIVES AS MODEL FOR THE SYNTHESIS OF TALAROMYCINS

  摘要：

  The synthesis of 3,5-dideoxy-1,2-O-isopropylidene-5-C-hydroxymethyl-beta -D-erythro- (1) and alpha -L-threo-hexulopyranose (2) from 3-deoxy-1,2-O-isopropylidene-beta -D-erythro-hexulopyranose (5) from D-fructose is described, as well as their respective transformation into 3,5-dideoxy-1,2-O-isopropylidene-5-C-hydroxymethyl-beta -D-threo- (3) and -alpha -L-erythro-hexulopyranose (4) by inversion of configuration at C-4.

  DOI：

  10.1081/car-100106928
• 作为产物：
  描述：

  4-O-tert-butyldiphenylsilyl-3,5-dideoxy-1,2-O-isopropylidene-5-C-methylene-β-D-glycero-hexulopyranose 在 sodium hydroxide 、 dimethyl sulfide borane 、 四丁基氟化铵 、 双氧水 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 11.5h， 生成 5-C-benzoyloxymethyl-3,5-dideoxy-1,2-O-isopropylidene-β-D-erythro-hexulopyranose
  参考文献：
  名称：

  SYNTHESIS OF BRANCHED-CHAIN HEXULOSE DERIVATIVES AS MODEL FOR THE SYNTHESIS OF TALAROMYCINS

  摘要：

  The synthesis of 3,5-dideoxy-1,2-O-isopropylidene-5-C-hydroxymethyl-beta -D-erythro- (1) and alpha -L-threo-hexulopyranose (2) from 3-deoxy-1,2-O-isopropylidene-beta -D-erythro-hexulopyranose (5) from D-fructose is described, as well as their respective transformation into 3,5-dideoxy-1,2-O-isopropylidene-5-C-hydroxymethyl-beta -D-threo- (3) and -alpha -L-erythro-hexulopyranose (4) by inversion of configuration at C-4.

  DOI：

  10.1081/car-100106928

文献信息

• SYNTHESIS OF BRANCHED-CHAIN HEXULOSE DERIVATIVES AS MODEL FOR THE SYNTHESIS OF TALAROMYCINS
  作者：Isidoro Izquierdo、María T. Plaza、Miguel Rodríguez、Juan A. Tamayo、Leocadia Macias

  DOI：10.1081/car-100106928

  日期：2001.7.31

  The synthesis of 3,5-dideoxy-1,2-O-isopropylidene-5-C-hydroxymethyl-beta -D-erythro- (1) and alpha -L-threo-hexulopyranose (2) from 3-deoxy-1,2-O-isopropylidene-beta -D-erythro-hexulopyranose (5) from D-fructose is described, as well as their respective transformation into 3,5-dideoxy-1,2-O-isopropylidene-5-C-hydroxymethyl-beta -D-threo- (3) and -alpha -L-erythro-hexulopyranose (4) by inversion of configuration at C-4.