methyl (4S,5R,6R)-4,5,7-tris(benzyloxy)-6-hydroxyhept-2-enoate | 56703-54-9

• 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: methyl (4S,5R,6R)-4,5,7-tris(benzyloxy)-6-hydroxyhept-2-enoate
• 英文别名: methyl (E,4S,5R,6R)-6-hydroxy-4,5,7-tris(phenylmethoxy)hept-2-enoate
• CAS: 56703-54-9
• 化学式: C₂₉H₃₂O₆
• 分子量: 476.569
• InChiKey: WRZGYXPJTYTPQQ-PVAWTMSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  35
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,3,5-三-O-苄基呋喃戊糖 、 甲氧羰基亚甲基三苯基正膦 在 苯甲酸 作用下， 以 乙腈 为溶剂， 反应 0.83h， 以60%的产率得到(Z)-(4S,5R,6R)-4,5,7-Tris-benzyloxy-6-hydroxy-hept-2-enoic acid methyl ester
  参考文献：
  名称：

  Synthesis of Imidazole C1- and C3-Ribonucleoside Phosphoramidites for Probing Catalytic Mechanism in Ribozyme

  摘要：

  Synthesis of C4-linked imidazole N-pivaloyloxymethyl (P0M)-2'-O-cyanoethylated (CE) C-1- and C-3-ribonucleoside phosphoramidites 1a and 1b is described. These phosphoramidite products were incorporated into RNA sequence through solid phase phosphoramidite approach, providing RNA with imidazole linked through different length to sugar residue, to study the mechanism of a ribozyme.

  DOI：

  10.3987/com-11-12263

文献信息

• Application of a tandem seleno-michael/aldol reaction in the total syntheses of (+)-Pericosine B, (+)-Pericosine C, (+)-COTC and 7-chloro-analogue of (+)-Gabosine C
  作者：Natalia Biduś、Piotr Banachowicz、Szymon Buda

  DOI：10.1016/j.tet.2020.131397

  日期：2020.8

  Synthesis of (+)-Pericosine B, (+)-Pericosine C, (+)-COTC and a 7-chloro-analogue of (+)-Gabosine C was achieved via tandem seleno-Michael/aldol reactions as key steps. The carbasugar linear precursor was obtained from cheap and readily available d-ribose in 7 steps which included resolution of the d-ribopyranose and the d-ribofuranose forms. Further transformation of the cyclic product involving a

  （+）-Pericosine B，（+）-Pericosine C，（+）-COTC和（+）-Gabosine C的7-氯类似物的合成是通过串联硒代-Michael / aldol反应作为关键步骤实现的。Carbasugar线性前体可通过7个步骤从廉价且容易获得的d-核糖中获得，包括拆分d-核糖吡喃糖和d-核呋喃糖形式。涉及区域选择性Steglich酯化或仲羟基甲基化的环状产物的进一步转化产生了受保护的（+）-COTC，（+）-Pericosine B和（+）-PericosineC。苄基醚在-78°脱保护C以令人满意的产率得到标题化合物。
• Seven-membered ring nucleosides
  申请人：Storer Richard

  公开号：US20070185063A1

  公开（公告）日：2007-08-09

  The present invention provides nucleoside analogue compounds that treat a host infected with a Flaviviridae virus infection, or other viruses that exhibit RNA-dependent RNA viral replication, compositions comprising these compounds and methods of using the compounds for the treatment and/or prophylaxis of viral infection, especially hepatitis C, in an infected host.
• Synthesis of Imidazole C1- and C3-Ribonucleoside Phosphoramidites for Probing Catalytic Mechanism in Ribozyme
  作者：Shinya Harusawa、Kensuke Fujii、Masayoshi Nishiura、Lisa Araki、Yoshihide Usami、Zheng-yun Zhao、David M. J. Lilley

  DOI：10.3987/com-11-12263

  日期：——

  Synthesis of C4-linked imidazole N-pivaloyloxymethyl (P0M)-2'-O-cyanoethylated (CE) C-1- and C-3-ribonucleoside phosphoramidites 1a and 1b is described. These phosphoramidite products were incorporated into RNA sequence through solid phase phosphoramidite approach, providing RNA with imidazole linked through different length to sugar residue, to study the mechanism of a ribozyme.