(-)-((3aS,4R/S,6S,6aS)-4-hydroxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-3a,6-diyl)dimethanol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-((3aS,4R/S,6S,6aS)-4-hydroxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-3a,6-diyl)dimethanol
• 英文别名: (3aS,6S,6aS)-3a,6-bis(hydroxymethyl)-2,2-dimethyl-6,6a-dihydro-4H-furo[3,4-d][1,3]dioxol-4-ol
• 化学式: C₉H₁₆O₆
• 分子量: 220.222
• InChiKey: JLEGEDDIMHKLAR-GOXMAWJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  15
• 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：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (-)-((3aS,4R/S,6S,6aS)-4-hydroxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-3a,6-diyl)dimethanol 在 sodium tetrahydroborate 作用下， 以 水 为溶剂， 生成
  参考文献：
  名称：

  Doubly carbon-branched pentoses: synthesis of both enantiomers of 2,4-di-C-methyl arabinose and 2-deoxy-2,4-di-C-methyl arabinose using only acetonide protection

  摘要：

  An acetonide is the only protecting group used in the synthesis of both the enantiomers of 2,4-di-C-methyl arabinose and 2-deoxy-2,4-di-C-methyl arabinose via the enantiomeric 3-C-methyl-L-erythronolactone [from 2-C-methyl-D-ribono-lactone or D-ribose] and 3-C-methyl-D-erythronolactone [from D-tagatose Or L-ribose]. NMR studies on unprotected C-methyl arabinoses show that methyl branching significantly affects the ratios of pyranose and furanose forms present in aqueous Solution. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.06.098
• 作为产物：
  描述：

  在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以84%的产率得到(-)-((3aS,4R/S,6S,6aS)-4-hydroxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-3a,6-diyl)dimethanol
  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

文献信息

• Doubly carbon-branched pentoses: synthesis of both enantiomers of 2,4-di-C-methyl arabinose and 2-deoxy-2,4-di-C-methyl arabinose using only acetonide protection
  作者：K. Victoria Booth、Sarah F. Jenkinson、Daniel Best、Fernando Fernández Nieto、Ramón J. Estévez、Mark R. Wormald、Alexander C. Weymouth-Wilson、George W.J. Fleet

  DOI：10.1016/j.tetlet.2009.06.098

  日期：2009.9

  An acetonide is the only protecting group used in the synthesis of both the enantiomers of 2,4-di-C-methyl arabinose and 2-deoxy-2,4-di-C-methyl arabinose via the enantiomeric 3-C-methyl-L-erythronolactone [from 2-C-methyl-D-ribono-lactone or D-ribose] and 3-C-methyl-D-erythronolactone [from D-tagatose Or L-ribose]. NMR studies on unprotected C-methyl arabinoses show that methyl branching significantly affects the ratios of pyranose and furanose forms present in aqueous Solution. (C) 2009 Elsevier Ltd. All rights reserved.
• Efficient and practical synthesis of l-hamamelose
  作者：Won Hee Kim、Jin-Ah Kang、Hyung-Rock Lee、Ah-Young Park、Pusoon Chun、Boeun Lee、Jungsu Kim、Jin-Ah Kim、Lak Shin Jeong、Hyung Ryong Moon

  DOI：10.1016/j.carres.2009.09.011

  日期：2009.11

  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.