(3aR,4R,5Z,5aS,9aR,9bS)-5-benzylidene-2,2,8,8-tetramethyl hexahydro-3aH-[1,3]dioxolo[4,5-h][1,3]benzodioxin-4-ol | 631918-09-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,4R,5Z,5aS,9aR,9bS)-5-benzylidene-2,2,8,8-tetramethyl hexahydro-3aH-[1,3]dioxolo[4,5-h][1,3]benzodioxin-4-ol
• 英文别名: (1R,2S,6R,7R,8Z,9S)-8-benzylidene-4,4,12,12-tetramethyl-3,5,11,13-tetraoxatricyclo[7.4.0.02,6]tridecan-7-ol
• CAS: 631918-09-7
• 化学式: C₂₀H₂₆O₅
• 分子量: 346.423
• InChiKey: AZJLGLWREICYDV-ZYQPTJERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 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,5Z,5aS,9aR,9bS)-5-benzylidene-2,2,8,8-tetramethyl hexahydro-3aH-[1,3]dioxolo[4,5-h][1,3]benzodioxin-4-ol 在 sodium tetrahydroborate 、 cerium(III) chloride 、 sodium hydride 、 臭氧 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 (3aR,4R,5aR,9aR,9bS)-4-(benzyloxy)-2,2,8,8-tetramethylhexahydro-3aH-[1,3]dioxolo[4,5-h][1,3]benzodioxin-5-ol
  参考文献：
  名称：

  Stereodivergent synthesis of 5a-carba-hexopyranoses from carbohydrates via 6-exo-dig radical cyclization: preparation of 5a-carba-β-d-manno-, α-d-allo-, β-l-talo- and α-l-gulopyranose pentaacetates from d-mannose

  摘要：

  Four carbasugars. 5a-carba-beta-D-manno-, alpha-D-allo-, beta-L-talo- and alpha-L-gulopyranose pentaacetates, have been prepared in a stereodivergent manner from D-mannose. Alkynyl derivatives of 2,3:4,6-di-O-isopropylidene-D-mannopyranose, which are prepared by homologation at C-1. by reaction with phenyl acetylide, undergo a 6-exo-dig radical cyclization, from a radical located at C-5. to yield a mixture of highly functionalized cyclohexanes. Some of these compounds, after transformation of their exocyclic double bond in a hydroxy function, were correlated with polyhydroxylated cyclohexanes, which were then selectively deoxygenated either at position C-4 or C-5a (carbohydrate numbering) to afford carbasugars of the D- Or L- series. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00532-9
• 作为产物：
  描述：

  1-phenyl-1,2-dideoxy-7-O-(phenoxythiocrbonyl)-4,5:6,8-di-O-isopropylidene-D-talo-D-glycero-oct-1-yne 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以24%的产率得到(3aR,4R,5Z,5aS,9aR,9bS)-5-benzylidene-2,2,8,8-tetramethyl hexahydro-3aH-[1,3]dioxolo[4,5-h][1,3]benzodioxin-4-ol
  参考文献：
  名称：

  Stereodivergent synthesis of 5a-carba-hexopyranoses from carbohydrates via 6-exo-dig radical cyclization: preparation of 5a-carba-β-d-manno-, α-d-allo-, β-l-talo- and α-l-gulopyranose pentaacetates from d-mannose

  摘要：

  Four carbasugars. 5a-carba-beta-D-manno-, alpha-D-allo-, beta-L-talo- and alpha-L-gulopyranose pentaacetates, have been prepared in a stereodivergent manner from D-mannose. Alkynyl derivatives of 2,3:4,6-di-O-isopropylidene-D-mannopyranose, which are prepared by homologation at C-1. by reaction with phenyl acetylide, undergo a 6-exo-dig radical cyclization, from a radical located at C-5. to yield a mixture of highly functionalized cyclohexanes. Some of these compounds, after transformation of their exocyclic double bond in a hydroxy function, were correlated with polyhydroxylated cyclohexanes, which were then selectively deoxygenated either at position C-4 or C-5a (carbohydrate numbering) to afford carbasugars of the D- Or L- series. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00532-9