(3aR,4R,6aS)-2,2-dimethyl-5-((tetrahydro-2H-pyran-2-yloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-ol | 1403598-61-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (3aR,4R,6aS)-2,2-dimethyl-5-((tetrahydro-2H-pyran-2-yloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-ol
• 英文别名: (3aR,4R,6aS)-2,2-dimethyl-5-(oxan-2-yloxymethyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-ol
• CAS: 1403598-61-7
• 化学式: C₁₄H₂₂O₅
• 分子量: 270.326
• InChiKey: SSPXSRJWKXPTSU-USLXRJLDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3aR,4R,6aS)-2,2-dimethyl-5-((tetrahydro-2H-pyran-2-yloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-ol 在 盐酸 、 偶氮二甲酸二异丙酯 、 10% Pd/C 、 氢气 、 三苯基膦 、 对硝基苯甲酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.25h， 生成 (1S,2S,3S,4S)-4-(hydroxymethyl)cyclopentane-1,2,3-triol
  参考文献：
  名称：

  Synthesis of 4a-carba-β-l-lyxofuranose, 4a-carba-β-l-arabinofuranose and 2,2,5-trimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one using Mn/CrCl3 mediated domino reactions and ring closing metathesis

  摘要：

  A common method for the synthesis of 4a-carba-beta-L-lyxofuranose and 4a-carba-beta-L-arabinofuranose from D-mannose and 2,2,5-trimethy1-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one from o-ribose is described using catalytic Nozaki-Hiyama-Kishi (NHK) conditions and ring closing metathesis (RCM). In this transformation, omega-deoxy-omega-iodo manno/ribo furanoside undergoes reductive elimination in the presence of Mn/CrCl3 to give the corresponding olefin-aldehyde which was trapped by nucleophile under the same conditions to afford the desired diolefinic species. The ring closing metathesis reaction on these diolefinic species with Grubbs second generation catalyst produced the required carbocycles. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.07.014
• 作为产物：
  描述：

  (3aS,6aS)-2,2-dimethyl-5-((tetrahydro-2H-pyran-2-yloxy)methyl)-3aH-cyclopenta[d][1,3]dioxol-4(6aH)-one 在 sodium tetrahydroborate 、 cerium(III) chloride heptahydrate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 以93%的产率得到(3aR,4R,6aS)-2,2-dimethyl-5-((tetrahydro-2H-pyran-2-yloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-ol
  参考文献：
  名称：

  Synthesis of 4a-carba-β-l-lyxofuranose, 4a-carba-β-l-arabinofuranose and 2,2,5-trimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one using Mn/CrCl3 mediated domino reactions and ring closing metathesis

  摘要：

  A common method for the synthesis of 4a-carba-beta-L-lyxofuranose and 4a-carba-beta-L-arabinofuranose from D-mannose and 2,2,5-trimethy1-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one from o-ribose is described using catalytic Nozaki-Hiyama-Kishi (NHK) conditions and ring closing metathesis (RCM). In this transformation, omega-deoxy-omega-iodo manno/ribo furanoside undergoes reductive elimination in the presence of Mn/CrCl3 to give the corresponding olefin-aldehyde which was trapped by nucleophile under the same conditions to afford the desired diolefinic species. The ring closing metathesis reaction on these diolefinic species with Grubbs second generation catalyst produced the required carbocycles. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.07.014