(1S,2S,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-(hydroxymethyl)cyclohexane-1,2-diol | 622832-80-8

• 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: (1S,2S,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-(hydroxymethyl)cyclohexane-1,2-diol
• 英文别名: (1S,2S,3S,4R,5S,6S)-3-(hydroxymethyl)-4,5,6-tris(phenylmethoxy)cyclohexane-1,2-diol
• CAS: 622832-80-8
• 化学式: C₂₈H₃₂O₆
• 分子量: 464.558
• InChiKey: ATARRQGBWKQLGV-XDHPVKSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S,2S,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-(hydroxymethyl)cyclohexane-1,2-diol 在 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 甲醇 为溶剂， 反应 98.5h， 生成 ((1R,2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-7-oxabicyclo-[4.1.0]heptan-2-yl)methanol (+)-2,3,4-tri-O-benzylcyclophellitol
  参考文献：
  名称：

  Conversion of d-Glucose to Cyclitol with Hydroxymethyl Substituent via Intramolecular Silyl Nitronate Cycloaddition Reaction:  Application to Total Synthesis of (+)-Cyclophellitol

  摘要：

  [GRAPHICS]A diastereoisomeric mixture of 1-nitro-6-heptene-2,3,4,5-tetraol derivative (A) was prepared by Henry reaction between D-glucose-based aldehyde and nitromethane. Only the (2S)-isomer of A led to cyclitol (B) via nitronate-olefin cycloaddition on treatment with TMS-Cl and Et3N in the presence of catalytic DMAP followed by acid treatment. (+)-Cyclophellitol (1) was synthesized from B in eight steps.

  DOI：

  10.1021/ol035424n
• 作为产物：
  描述：

  alpha-甲基葡萄糖甙 在 4-二甲氨基吡啶 、 三甲基氯硅烷 、 hexacarbonyl molybdenum 、 四溴化碳 、 dimethyl sulfide borane 、 sodium hydride 、 二异丁基氢化铝 、 对甲苯磺酸 、 三乙胺 、 三苯基膦 、 锌 、 四甲基胍 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 113.0h， 生成 (1S,2S,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-(hydroxymethyl)cyclohexane-1,2-diol
  参考文献：
  名称：

  Conversion of d-Glucose to Cyclitol with Hydroxymethyl Substituent via Intramolecular Silyl Nitronate Cycloaddition Reaction:  Application to Total Synthesis of (+)-Cyclophellitol

  摘要：

  [GRAPHICS]A diastereoisomeric mixture of 1-nitro-6-heptene-2,3,4,5-tetraol derivative (A) was prepared by Henry reaction between D-glucose-based aldehyde and nitromethane. Only the (2S)-isomer of A led to cyclitol (B) via nitronate-olefin cycloaddition on treatment with TMS-Cl and Et3N in the presence of catalytic DMAP followed by acid treatment. (+)-Cyclophellitol (1) was synthesized from B in eight steps.

  DOI：

  10.1021/ol035424n

文献信息

• Conversion of <scp>d</scp>-Glucose to Cyclitol with Hydroxymethyl Substituent via Intramolecular Silyl Nitronate Cycloaddition Reaction:  Application to Total Synthesis of (+)-Cyclophellitol
  作者：Teruhiko Ishikawa、Yoshihiro Shimizu、Takayuki Kudoh、Seiki Saito

  DOI：10.1021/ol035424n

  日期：2003.10.1

  [GRAPHICS]A diastereoisomeric mixture of 1-nitro-6-heptene-2,3,4,5-tetraol derivative (A) was prepared by Henry reaction between D-glucose-based aldehyde and nitromethane. Only the (2S)-isomer of A led to cyclitol (B) via nitronate-olefin cycloaddition on treatment with TMS-Cl and Et3N in the presence of catalytic DMAP followed by acid treatment. (+)-Cyclophellitol (1) was synthesized from B in eight steps.