1-[(4R,5R)-5-((1R,3R)-5-Benzyloxy-1,3-dimethoxy-pentyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethane-1,2-diol | 152035-85-3

• 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: 1-[(4R,5R)-5-((1R,3R)-5-Benzyloxy-1,3-dimethoxy-pentyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethane-1,2-diol
• 英文别名: 1-[(4R,5R)-5-[(1R,3R)-1,3-dimethoxy-5-phenylmethoxypentyl]-2,2-dimethyl-1,3-dioxolan-4-yl]ethane-1,2-diol
• CAS: 152035-85-3
• 化学式: C₂₁H₃₄O₇
• 分子量: 398.497
• InChiKey: RLUZEQZOUFPGKF-HRCBOCMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  86.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-[(4R,5R)-5-((1R,3R)-5-Benzyloxy-1,3-dimethoxy-pentyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethane-1,2-diol 在 吡啶 、 lithium aluminium tetrahydride 、 重铬酸吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 1-[(4S,5R)-5-((1R,3R)-5-Benzyloxy-1,3-dimethoxy-pentyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethanone
  参考文献：
  名称：

  Synthesis of acyclic polyol derivatives via enzyme-mediated aldol reaction

  摘要：

  Enzyme-mediated stereoselective aldol reaction between dihydroxyacetone phosphate (DHAP, 1) and (2R,4R)-6-benzyloxy-2,4-dimethoxyhexanal (8) was catalyzed by rabbit muscle aldolase (RAMA) to generate (3S,4R,5R,7R)-trihydroxyketone 12, which could be easily transformed to the masked polyhydroxylated compound 15 corresponding to the C-9 approximately C-16 segment of pentamycin (6).

  DOI：

  10.1016/s0040-4039(00)74050-0
• 作为产物：
  描述：

  (3S,4R,5R,7R)-9-benzyloxy-5,7-dimethoxy-1,3,4-trihydroxynonan-2-one 在 lithium aluminium tetrahydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 生成 1-[(4R,5R)-5-((1R,3R)-5-Benzyloxy-1,3-dimethoxy-pentyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethane-1,2-diol
  参考文献：
  名称：

  Synthesis of acyclic polyol derivatives via enzyme-mediated aldol reaction

  摘要：

  Enzyme-mediated stereoselective aldol reaction between dihydroxyacetone phosphate (DHAP, 1) and (2R,4R)-6-benzyloxy-2,4-dimethoxyhexanal (8) was catalyzed by rabbit muscle aldolase (RAMA) to generate (3S,4R,5R,7R)-trihydroxyketone 12, which could be easily transformed to the masked polyhydroxylated compound 15 corresponding to the C-9 approximately C-16 segment of pentamycin (6).

  DOI：

  10.1016/s0040-4039(00)74050-0

文献信息

• Synthesis of acyclic polyol derivatives via enzyme-mediated aldol reaction
  作者：Kazutsugu Matsumoto、Masayuki Shimagaki、Tadashi Nakata、Takeshi Oishi

  DOI：10.1016/s0040-4039(00)74050-0

  日期：1993.7

  Enzyme-mediated stereoselective aldol reaction between dihydroxyacetone phosphate (DHAP, 1) and (2R,4R)-6-benzyloxy-2,4-dimethoxyhexanal (8) was catalyzed by rabbit muscle aldolase (RAMA) to generate (3S,4R,5R,7R)-trihydroxyketone 12, which could be easily transformed to the masked polyhydroxylated compound 15 corresponding to the C-9 approximately C-16 segment of pentamycin (6).