3,5,6-trideoxy-1,2-O-isopropylidene-5-iodo-6-(methyl hex-1-ynoate)-5-O-trifluorosulfonyl-α-D-ribohexofuranose | 188255-12-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3,5,6-trideoxy-1,2-O-isopropylidene-5-iodo-6-(methyl hex-1-ynoate)-5-O-trifluorosulfonyl-α-D-ribohexofuranose
• 英文别名: methyl 8-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-8-iodooct-5-ynoate
• CAS: 188255-12-1
• 化学式: C₁₆H₂₃IO₅
• 分子量: 422.26
• InChiKey: JAPANSWRQWSAIT-MDRSIWMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 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：

  3,5,6-trideoxy-1,2-O-isopropylidene-5-iodo-6-(methyl hex-1-ynoate)-5-O-trifluorosulfonyl-α-D-ribohexofuranose 在 吡啶 、 mercury dichloride 、 mercury(II) oxide 、 zinc(II) chloride 作用下， 以 水 、 丙酮 为溶剂， 反应 33.0h， 生成 (8R,9S,11R)-methyl 8-iodo-9,11-di(triethylsilyloxy)-12-oxododec-5-ynoate
  参考文献：
  名称：

  Total Synthesis of (15R)- and (15S)-F_2t-Isoprostanes by a Biomimetic Process Using the Cyclization of Acyclic Dihydroxylated Octa-5,7-dienyl Radicals

  摘要：

  We report a new route to F-2t-IsoP (formerly named 8-epi-PGF(2alpha)) using a biomimetic radical cyclization of a highly functionalized C20 precursor. The strategy employed gives a beta-hydroxy free radical followed by molecular oxygen trapping, which is an unusual method for quenching carbon free radicals. We observed the formation of unique diastereoisomers (15R)- and (15S)-F-2t-IsoP. This result is consistent with a strong stereoelectronic control associated with a steric effect initiated by the side chains alpha and omega on the cyclopentane ring.

  DOI：

  10.1021/jo0109624
• 作为产物：
  描述：

  methyl (8R)-8-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-8-(trifluoromethylsulfonyloxy)oct-5-ynoate 在 四丁基碘化铵 作用下， 以 苯 为溶剂， 反应 1.0h， 以75%的产率得到3,5,6-trideoxy-1,2-O-isopropylidene-5-iodo-6-(methyl hex-1-ynoate)-5-O-trifluorosulfonyl-α-D-ribohexofuranose
  参考文献：
  名称：

  Total synthesis of 15(RS)-5,6-dehydro-8-epi-PGF2α methyl ester by a biomimetic process

  摘要：

  The first total synthesis of 15(RS)-5,6-dehydro-8-epi-PGF(2 alpha) methyl ester 1 with high stereoselectivity and good yield, is described using D-glucose as starting material. This novel isoprostane is a potent precursor of labelled (deutered and/or tritiated) 8-epi-PGF(2 alpha), an useful tool for biological studies. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00100-7