2,6-anhydro-4-O-(2-bromo-1-ethoxyethyl)-1,3-dideoxy-5,7-O-(1-methylethylidene)-D-arabino-hept-2-enitol | 401625-01-2

• 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: 2,6-anhydro-4-O-(2-bromo-1-ethoxyethyl)-1,3-dideoxy-5,7-O-(1-methylethylidene)-D-arabino-hept-2-enitol
• 英文别名: (4aR,8R,8aS)-8-(2-bromo-1-ethoxyethoxy)-2,2,6-trimethyl-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3]dioxine
• CAS: 401625-01-2
• 化学式: C₁₄H₂₃BrO₅
• 分子量: 351.238
• InChiKey: VTGGWERWJZIHBT-RFSNJIIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,6-anhydro-4-O-(2-bromo-1-ethoxyethyl)-1,3-dideoxy-5,7-O-(1-methylethylidene)-D-arabino-hept-2-enitol 在 jones reagent 、 偶氮二异丁腈 、 四丁基碘化铵 、 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醇 、 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-α-mannosyl chloride 在 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 2,6-anhydro-4-O-(2-bromo-1-ethoxyethyl)-1,3-dideoxy-5,7-O-(1-methylethylidene)-D-arabino-hept-2-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

• Stereocontrolled entry to β-C-glycosides and bis-C,C-glycosides from C-glycals: preparation of a highly functionalized triene from d-mannose
  作者：Ana M. Gómez、Marta Casillas、Serafı́n Valverde、J.Cristóbal López

  DOI：10.1016/s0957-4166(01)00363-9

  日期：2001.8

  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.