2-((2S,3S,4R)-2,4-dihydroxy-3,5-dimethylhexyl)-1,3-dithiane | 193405-66-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二噻烷
• 英文名称: 2-((2S,3S,4R)-2,4-dihydroxy-3,5-dimethylhexyl)-1,3-dithiane
• 英文别名: (2S,3S,4R)-1-(1,3-dithian-2-yl)-3,5-dimethylhexane-2,4-diol
• CAS: 193405-66-2
• 化学式: C₁₂H₂₄O₂S₂
• 分子量: 264.453
• InChiKey: UMGUDJFMZDNFMM-JBLDHEPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  91.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-((2S,3S,4R)-2,4-dihydroxy-3,5-dimethylhexyl)-1,3-dithiane 在 2,6-二甲基吡啶 、 六甲基磷酰三胺 、 草酰氯 、 氢氟酸 、 叔丁基锂 、 二异丁基氢化铝 、 对甲苯磺酸 、 二甲基亚砜 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 丙酮 、 乙腈 为溶剂， 反应 33.67h， 生成 (2R,3R,4S,6S,8R,10S)-4,10-Bis-(tert-butyl-dimethyl-silanyloxy)-8-[(E)-(4S,5S)-3,5-dimethyl-4-(2-trimethylsilanyl-ethoxymethoxy)-hepta-2,6-dienyl]-2-isopropyl-3-methyl-1,7-dioxa-spiro[5.5]undecane
  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 、 正丁基锂 、 bis(acetylacetonate)oxovanadium 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 24.0h， 生成 2-((2S,3S,4R)-2,4-dihydroxy-3,5-dimethylhexyl)-1,3-dithiane
  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

文献信息

• A convergent synthesis of the C(11)–C(25) fragment of the aglycone of avermectin A2b
  作者：Eric Menager、Eric Merifield、Mark Smallridge、Eric J. Thomas

  DOI：10.1016/s0040-4020(97)00590-5

  日期：1997.7

  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.