1,5-anhydro-4,6-O-isopropylidene-2-deoxy-1-C-methyl-D-arabino-hex-1-enitol | 184877-35-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 1,5-anhydro-4,6-O-isopropylidene-2-deoxy-1-C-methyl-D-arabino-hex-1-enitol
• 英文别名: 2,6-anhydro-1,3-dideoxy-5,7-O-(1-methylethylidene)-D-arabino-hept-2-enitol；(4aR,8R,8aS)-2,2,6-trimethyl-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3]dioxin-8-ol
• CAS: 184877-35-8
• 化学式: C₁₀H₁₆O₄
• 分子量: 200.235
• InChiKey: GPOSVLBOAVIUHC-HLTSFMKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,5-anhydro-4,6-O-isopropylidene-2-deoxy-1-C-methyl-D-arabino-hex-1-enitol 在 jones reagent 、 偶氮二异丁腈 、 四丁基碘化铵 、 sodium hydride 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 99.0h， 生成 (3aS,4R,6R,7S,7aR)-4-allyl-7-methoxy-6-(methoxymethyl)-4-methyltetrahydro-4H-furo[3,2-c]pyran-2(3H)-one
  参考文献：
  名称：

  Stereocontrolled entry to β-C-glycosides and bis-C,C-glycosides from C-glycals: preparation of a highly functionalized triene from d-mannose

  摘要：

  The C(3) hydroxyl group of C-glycals can be readily converted into mixed halo-acetals of 2-bromo-acetaldehyde. Radical reaction of the latter mediated by tri-n-butyltin hydride, with or without a radical acceptor, led diastereoselectively to either beta -C-glycosides or bis-C,C-glycosides, respectively. The latter have been transformed into a highly functionalized triene, which is a potential precursor in a proposed synthesis of labdane type diterpenes from D-mannose. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00363-9
• 作为产物：
  描述：

  2,3:4,6-di-O-isopropylidene-D-mannopyranose 在 四氯化碳 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 1,5-anhydro-4,6-O-isopropylidene-2-deoxy-1-C-methyl-D-arabino-hex-1-enitol
  参考文献：
  名称：

  Stereocontrolled entry to β-C-glycosides and bis-C,C-glycosides from C-glycals: preparation of a highly functionalized triene from d-mannose

  摘要：

  The C(3) hydroxyl group of C-glycals can be readily converted into mixed halo-acetals of 2-bromo-acetaldehyde. Radical reaction of the latter mediated by tri-n-butyltin hydride, with or without a radical acceptor, led diastereoselectively to either beta -C-glycosides or bis-C,C-glycosides, respectively. The latter have been transformed into a highly functionalized triene, which is a potential precursor in a proposed synthesis of labdane type diterpenes from D-mannose. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00363-9

文献信息

• Synthesis of<i>C</i>-1 Alkyl and Aryl Glycals from Pyranosyl or Furanosyl Chlorides by Treatment with Organolithium Reagents
  作者：Ana M. Gómez、Ana Pedregosa、Marta Casillas、Clara Uriel、J. Cristóbal López

  DOI：10.1002/ejoc.200900417

  日期：2009.7

  Glycosyl chlorides, with ether or isopropylidene acetal protecting groups, readily available from furanoses or pyranoses, can be conveniently transformed into C-1 alkyl or aryl glycals by reaction with alkyl or aryl organolithium reagents.

  具有醚或亚异丙基缩醛保护基团的糖基氯可容易地从呋喃糖或吡喃糖中获得，可通过与烷基或芳基有机锂试剂反应方便地转化为 C-1 烷基或芳基糖醛。
• Expeditious entry to C-alkyl and C-aryl pyranoid glycals: reaction of anomeric glycosyl chlorides with organolithiums
  作者：Ana M. Gómez、Marta Casillas、Serafín Valverde、J. Cristóbal López

  DOI：10.1039/cc9960002357

  日期：——

  Treatment of ether-substituted glycopyranosyl chlorides with organolithium reagents gives the corresponding C-glycals in acceptable to good yields.