(3aR,6aS)-6-(iodomethyl)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole | 1403598-71-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,6aS)-6-(iodomethyl)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole
• CAS: 1403598-71-9
• 化学式: C₉H₁₅IO₄
• 分子量: 314.12
• InChiKey: AAEYGFITCYWQDV-MIDKJMSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3aR,6aS)-6-(iodomethyl)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 pyridinium dichlorochromate 、 nickel dichloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.5h， 生成 (3aR,6aR)-2,2,5-trimethyl-3aH-cyclopenta[d][1,3]dioxol-4(6aH)-one
  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：

  [(3aR,6aR)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methanol 在 咪唑 、 碘 、 tetraphenylporphyrin 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (3aR,6aS)-6-(iodomethyl)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole
  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

文献信息

• 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
  作者：Girija Prasad Mishra、Bejugam Santhosh Kumar、B. Venkateswara Rao

  DOI：10.1016/j.tetasy.2012.07.014

  日期：2012.8

  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.