(3aS,4R,6R,7S,7aR)-4-allyl-7-methoxy-6-(methoxymethyl)-4-methyltetrahydro-4H-furo[3,2-c]pyran-2(3H)-one | 401625-07-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aS,4R,6R,7S,7aR)-4-allyl-7-methoxy-6-(methoxymethyl)-4-methyltetrahydro-4H-furo[3,2-c]pyran-2(3H)-one
• 英文别名: (3aS,4R,6R,7S,7aR)-7-methoxy-6-(methoxymethyl)-4-methyl-4-prop-2-enyl-3a,6,7,7a-tetrahydro-3H-furo[3,2-c]pyran-2-one
• CAS: 401625-07-8
• 化学式: C₁₄H₂₂O₅
• 分子量: 270.326
• InChiKey: AOWNLFWXOKZXEX-NRFQWKTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3aS,4R,6R,7S,7aR)-4-allyl-7-methoxy-6-(methoxymethyl)-4-methyltetrahydro-4H-furo[3,2-c]pyran-2(3H)-one 在 dimethyl sulfide borane 、 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.75h， 以70%的产率得到(3aS,4R,6R,7S,7aR)-4-(3-hydroxypropyl)-7-methoxy-6-(methoxymethyl)-4-methylhexahydro-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 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 102.0h， 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

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.