(4R,5R)-4-benzyloxymethyl-5-but-3-enyl-2,2-dimethyl-[1,3]dioxolane | 860267-59-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4R,5R)-4-benzyloxymethyl-5-but-3-enyl-2,2-dimethyl-[1,3]dioxolane
• 英文别名: (4R,5R)-4-but-3-enyl-2,2-dimethyl-5-(phenylmethoxymethyl)-1,3-dioxolane
• CAS: 860267-59-0
• 化学式: C₁₇H₂₄O₃
• 分子量: 276.376
• InChiKey: JDYIBOXJFGOFDD-HZPDHXFCSA-N

物化性质

• 沸点：
  354.5±27.0 °C(predicted)
• 密度：
  0.988±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R,5R)-4-benzyloxymethyl-5-but-3-enyl-2,2-dimethyl-[1,3]dioxolane 在 四氧化锇 N-甲基吗啉 、 甲醇 、 sodium hydroxide 、 sodium periodate 、 正丁基锂 、 samarium diiodide 、 D(+)-10-樟脑磺酸 、 四丁基碘化铵 、 zinc trifluoromethanesulfonate 、 sodium hydride 、 二异丁基氢化铝 、 碳酸氢钠 、 N,N-二异丙基乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 、 碘甲烷 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 、 叔丁醇 为溶剂， 反应 108.5h， 生成 (2R,3R,6R)-6-((R)-1,2-Bis-benzyloxy-ethyl)-3-methoxymethoxy-2-((Z)-tetradec-2-enyl)-tetrahydro-pyran
  参考文献：
  名称：

  Total Synthesis of the Proposed Structure for Pyragonicin

  摘要：

  The total synthesis of acetogenin 1 reported for pyragonicin and its 10-epimer 32 is described. The common THP ring system was stereoselectively constructed through a SMI2-induced reductive cyclization of beta-alkoxy acrylate 5 followed by Mitsunobu inversion, and each chiral center at C-10 was created by Brown's asymmetric allylation. Compound 1 had spectroscopic data consistent with that of natural pyragonicin, but a different optical rotation.

  DOI：

  10.1021/ol0508126
• 作为产物：
  描述：

  (-)-2,3-O-亚异丙基-D-苏力糖醇 在 sodium hydride 、 三乙胺 、 copper(I) bromide 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.75h， 生成 (4R,5R)-4-benzyloxymethyl-5-but-3-enyl-2,2-dimethyl-[1,3]dioxolane
  参考文献：
  名称：

  Total Synthesis of the Proposed Structure for Pyragonicin

  摘要：

  The total synthesis of acetogenin 1 reported for pyragonicin and its 10-epimer 32 is described. The common THP ring system was stereoselectively constructed through a SMI2-induced reductive cyclization of beta-alkoxy acrylate 5 followed by Mitsunobu inversion, and each chiral center at C-10 was created by Brown's asymmetric allylation. Compound 1 had spectroscopic data consistent with that of natural pyragonicin, but a different optical rotation.

  DOI：

  10.1021/ol0508126

文献信息

• Facile enantiospecific synthesis of (+)-iso-cladospolide B
  作者：Kavirayani R. Prasad、Vasudeva Rao Gandi

  DOI：10.1016/j.tetasy.2010.01.011

  日期：2010.3

  Enantiospecific synthesis of bio-active butenolide (+)-iso-cladospolide B from D-(-)-tartaric acid in a short synthetic sequence is presented. Pivotal reaction sequence includes cross metathesis of an alkene and Wittig olefination. (C) 2010 Elsevier Ltd. All rights reserved.
• Total Synthesis of the Proposed Structure for Pyragonicin
  作者：Shunya Takahashi、Narihito Ogawa、Hiroyuki Koshino、Tadashi Nakata

  DOI：10.1021/ol0508126

  日期：2005.6.1

  The total synthesis of acetogenin 1 reported for pyragonicin and its 10-epimer 32 is described. The common THP ring system was stereoselectively constructed through a SMI2-induced reductive cyclization of beta-alkoxy acrylate 5 followed by Mitsunobu inversion, and each chiral center at C-10 was created by Brown's asymmetric allylation. Compound 1 had spectroscopic data consistent with that of natural pyragonicin, but a different optical rotation.