| 1202058-62-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 1202058-62-5
• 化学式: C₂₂H₄₄O₅Si₂
• 分子量: 444.759
• InChiKey: PVWZESQCLCXUBQ-UKOCIUTBSA-N

反应信息

• 作为反应物：
  描述：

  在 sodium periodate 、 四氧化锇 作用下， 以 水 、 丙酮 为溶剂， 生成
  参考文献：
  名称：

  Efficient and practical synthesis of l-hamamelose

  摘要：

  An efficient synthetic route of L-hamamelose was successfully accomplished starting from D-ribose. L-Hamamelose was synthesized in 42% overall yield with six reaction steps via a stereoselective Grignard reaction, a stereoselective crossed aldol reaction and a controlled oxidative cleavage of the double bond of a vinyl diol compound. During the oxidative cleavage of the double bond of the vinyl diol compound with osmium tetroxide and NaIO4, an over-oxidative cleavage of alpha-hydroxyl aldehyde generated from ring opening of the first cleaved product, formyl lactol, did not occur, probably due to the stability of the lactol form. A plausible mechanism for the stereoselective crossed aldol reaction was suggested. final target compound, L-hamamelose can play a very important role as a chiral building block in synthesizing a wide variety of enantiopure compounds. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.09.011
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 、 (3aS,4R,6S,6aS) and (3aS,4S,6S,6aS)-3a-hydroxymethyl-2,2-dimethyl-6-vinyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ol 在 咪唑 作用下， 以 二氯甲烷 为溶剂， 以69%的产率得到
  参考文献：
  名称：

  Efficient and practical synthesis of l-hamamelose

  摘要：

  An efficient synthetic route of L-hamamelose was successfully accomplished starting from D-ribose. L-Hamamelose was synthesized in 42% overall yield with six reaction steps via a stereoselective Grignard reaction, a stereoselective crossed aldol reaction and a controlled oxidative cleavage of the double bond of a vinyl diol compound. During the oxidative cleavage of the double bond of the vinyl diol compound with osmium tetroxide and NaIO4, an over-oxidative cleavage of alpha-hydroxyl aldehyde generated from ring opening of the first cleaved product, formyl lactol, did not occur, probably due to the stability of the lactol form. A plausible mechanism for the stereoselective crossed aldol reaction was suggested. final target compound, L-hamamelose can play a very important role as a chiral building block in synthesizing a wide variety of enantiopure compounds. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.09.011