(1S,3S,4aR,8aR,9aS,10aR)-3-Benzyloxy-4,4-difluoro-8a,10a-dimethoxy-1-methyl-decahydro-2,9,10-trioxa-anthracene | 202717-79-1

• 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: (1S,3S,4aR,8aR,9aS,10aR)-3-Benzyloxy-4,4-difluoro-8a,10a-dimethoxy-1-methyl-decahydro-2,9,10-trioxa-anthracene
• CAS: 202717-79-1
• 化学式: C₂₁H₂₈F₂O₆
• 分子量: 414.447
• InChiKey: BZEWCZZMSAHPSG-DDKAMPBXSA-N

反应信息

• 作为反应物：
  描述：

  (1S,3S,4aR,8aR,9aS,10aR)-3-Benzyloxy-4,4-difluoro-8a,10a-dimethoxy-1-methyl-decahydro-2,9,10-trioxa-anthracene 在 palladium on activated charcoal 4-二甲氨基吡啶 、 四丁基溴化铵 、 水 、 氢气 、 二正丁基氧化锡 、 三氟乙酸 作用下， 以 吡啶 、 甲醇 、 乙酸乙酯 为溶剂， 25.0 ℃ 、100.0 kPa 条件下， 反应 3.33h， 生成 4-O-benzoyl-2-deoxy-2,2-difluoro-3-O-methyl-α-L-rhamnopyranose
  参考文献：
  名称：

  An Improved Synthesis of 4-O-Benzoyl-2,2-difluorooleandrose from l-Rhamnose. Factors Determining the Synthesis of 2,2-Difluorocarbohydrates from 2-Uloses

  摘要：

  4-O-Benzoyl-2,2-difluorooleandrose (16) has been synthesized from L-rhamnose. The key steps are the formation of a difluoromethylene group in 12 by reacting ulose 11 with DAST and the chemoselective methylation of diol 13 to give compound 14. To obtain the 2,2-difluoro compound 12, the substituents in the neighborhood of the carbonyl group in ulose 11 must be equatorial and the sugar ring must have restricted conformational mobility. This was done using 1,1,2,2-tetramethoxycyclohexane (TMC) to protect the hydroxyls at positions 3 and 4 in the sugar ring.

  DOI：

  10.1021/jo971846x
• 作为产物：
  描述：

  (1S,3S,4aR,8aR,9aS,10aR)-3-Benzyloxy-8a,10a-dimethoxy-1-methyl-octahydro-2,9,10-trioxa-anthracen-4-one 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以69%的产率得到(1S,3S,4aR,8aR,9aS,10aR)-3-Benzyloxy-4,4-difluoro-8a,10a-dimethoxy-1-methyl-decahydro-2,9,10-trioxa-anthracene
  参考文献：
  名称：

  An Improved Synthesis of 4-O-Benzoyl-2,2-difluorooleandrose from l-Rhamnose. Factors Determining the Synthesis of 2,2-Difluorocarbohydrates from 2-Uloses

  摘要：

  4-O-Benzoyl-2,2-difluorooleandrose (16) has been synthesized from L-rhamnose. The key steps are the formation of a difluoromethylene group in 12 by reacting ulose 11 with DAST and the chemoselective methylation of diol 13 to give compound 14. To obtain the 2,2-difluoro compound 12, the substituents in the neighborhood of the carbonyl group in ulose 11 must be equatorial and the sugar ring must have restricted conformational mobility. This was done using 1,1,2,2-tetramethoxycyclohexane (TMC) to protect the hydroxyls at positions 3 and 4 in the sugar ring.

  DOI：

  10.1021/jo971846x