(3R,4R,5R)-5,6-epoxy-2,4-dimethylhexan-3-ol | 193405-50-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4R,5R)-5,6-epoxy-2,4-dimethylhexan-3-ol
• CAS: 193405-50-4
• 化学式: C₈H₁₆O₂
• 分子量: 144.214
• InChiKey: ORSOQIVVZCCHLO-BIIVOSGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.04
• 重原子数：
  10.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.76
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (3R,4R,5R)-5,6-epoxy-2,4-dimethylhexan-3-ol 在 2,6-二甲基吡啶 、 六甲基磷酰三胺 、 正丁基锂 、 氢氟酸 、 四丁基氟化铵 、 叔丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 、 乙腈 为溶剂， 反应 231.0h， 生成 (E)-4-[(2R,4S,6S,8R,9R,10S)-4,10-Bis-(tert-butyl-dimethyl-silanyloxy)-8-isopropyl-9-methyl-1,7-dioxa-spiro[5.5]undec-2-yl]-2-methyl-but-2-enoic acid ethyl ester
  参考文献：
  名称：

  A convergent synthesis of the C(11)–C(25) fragment of the aglycone of avermectin A2b

  摘要：

  Oxidation of the mixture of products obtained by treatment of (S)-2-methylbutanal 8 with the E-but-2-enyldi-isopinocampheylborane prepared from (+)-pinene gave a mixture of homoallylic alcohols from which the major isomer 9 was isolated by chromatography. Oxidation with vanadylacetoacetate and tert-butyl hydroperoxide gave the epoxides 12 and 13, ratio 80 : 20. Following procedures developed in a synthesis of the model spiroacetal 19, 1,3-dithiane was alkylated, firstly using the epoxide 12, and then, after protection of the product 21 so obtained as its acetonide 23, using the epoxide 25, to give the 2,2-dialkylated 1,3-dithiane 25. Deprotection was accompanied by cyclisation to give the spiroacetal 28. Spiroacetal 29 was similarly prepared and taken through to the C(11)-C(25) fragment 38 of the aglycone of avermectin A(2b) 3. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00590-5
• 作为产物：
  描述：

  (3R,4S)-2,4-dimethylhex-5-en-3-ol 在 叔丁基过氧化氢 、 bis(acetylacetonate)oxovanadium 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 24.0h， 以57%的产率得到(3R,4R,5R)-5,6-epoxy-2,4-dimethylhexan-3-ol
  参考文献：
  名称：

  A convergent synthesis of the C(11)–C(25) fragment of the aglycone of avermectin A2b

  摘要：

  Oxidation of the mixture of products obtained by treatment of (S)-2-methylbutanal 8 with the E-but-2-enyldi-isopinocampheylborane prepared from (+)-pinene gave a mixture of homoallylic alcohols from which the major isomer 9 was isolated by chromatography. Oxidation with vanadylacetoacetate and tert-butyl hydroperoxide gave the epoxides 12 and 13, ratio 80 : 20. Following procedures developed in a synthesis of the model spiroacetal 19, 1,3-dithiane was alkylated, firstly using the epoxide 12, and then, after protection of the product 21 so obtained as its acetonide 23, using the epoxide 25, to give the 2,2-dialkylated 1,3-dithiane 25. Deprotection was accompanied by cyclisation to give the spiroacetal 28. Spiroacetal 29 was similarly prepared and taken through to the C(11)-C(25) fragment 38 of the aglycone of avermectin A(2b) 3. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00590-5