(1α,4α,5α)-1-(benzyloxy)-3-<(benzyloxy)methyl>-4,5-(isopropylidenedioxy)-2-cyclopentene | 126798-04-7

• 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: (1α,4α,5α)-1-(benzyloxy)-3-<(benzyloxy)methyl>-4,5-(isopropylidenedioxy)-2-cyclopentene
• 英文别名: (3aR,6S,6aS)-2,2-dimethyl-6-phenylmethoxy-4-(phenylmethoxymethyl)-6,6a-dihydro-3aH-cyclopenta[d][1,3]dioxole
• CAS: 126798-04-7
• 化学式: C₂₃H₂₆O₄
• 分子量: 366.457
• InChiKey: JQUHMLPWPJDCEP-BDTNDASRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1α,4α,5α)-1-(benzyloxy)-3-<(benzyloxy)methyl>-4,5-(isopropylidenedioxy)-2-cyclopentene 在 Lindlar's catalyst 甲醇 、 叠氮化锂 、 氢气 、 sodium methylate 、 sodium hydride 、 三氟乙酸 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 25.0~110.0 ℃ 、101.33 kPa 条件下， 反应 49.92h， 生成 (1β,2α,5α)-1-amino-2,5-bis(benzyloxy)-3-<(benzyloxy)methyl>-3-cyclopentene
  参考文献：
  名称：

  Synthesis and structural determination of (.+-.)-neplanocin F

  摘要：

  Neplanocin F (2), a minor constituent of the family of neplanocin antibiotics, was synthesized as a racemate in 12 steps from cyclopentenone 3/4, which in turn was available from D-ribonolactone. The carbocyclic ring of neplanocin F corresponds to the allylic rearranged isomer of the biologically active agent neplanocin A. Regiospecific reduction of the racemic cyclopentenone 3/4 and protection of the resulting alpha-alcohol as a benzyl ether 6 produced, after removal of the isopropylidene moiety, a compound (7) having allylic and homoallylic secondary alcohol functionalities. Differences in the reactivity of these two secondary alcohols were successfully manipulated to prepare the homoallylic substituted azide 14, which was then reduced and converted to the desired adenine ring by conventional methods. The spectral properties of the synthesized material [(+/-)-neplanocin F] were identical to those of the natural product, except for its lack of optical rotation. X-ray crystallographic analysis helped corroborate the structure. In contrast to its bioactive isomer, neoplanocin A, neplanocin F was devoid of cytotoxicity and in vitro antiviral activity.

  DOI：

  10.1021/jo00033a031
• 作为产物：
  描述：

  (4R,5R)-3-benzyloxymethyl-4,5-isopropylidenedioxycyclopent-2-enone 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 (1α,4α,5α)-1-(benzyloxy)-3-<(benzyloxy)methyl>-4,5-(isopropylidenedioxy)-2-cyclopentene
  参考文献：
  名称：

  （±）-neplanocin F的全合成

  摘要：

  （±）-Neplanocin F由外消旋体（/ ）分12步合成，该消旋体可从D-核糖内酯获得。

  DOI：

  10.1016/s0040-4039(01)80539-6

文献信息

• Enantioselective synthesis of (+)-neplanocin F
  作者：Marı́a J Comin、Julieta Leitofuter、Juan B Rodrı́guez

  DOI：10.1016/s0040-4020(02)00287-9

  日期：2002.4

  (+)-Neplanocin F ((+)-5), a minor component of the neplanocin family of antibiotics was enantioselectively synthesized starting from D-ribono-1,4-lactone via a convergent approach in 14 steps. This synthetic approach employed a regioselective protection of a secondary allylic hydroxyl group over a homoallylic one as key step. (C) 2002 Elsevier Science Ltd. All rights reserved.

  (+)–Neplanocin F ((+)-5) 是抗生素 neplanocin 家族中的一种次要成分，其对映选择性合成通过从 D-核糖-1,4-内酯出发，采用汇聚式方法，在 14 步反应中完成。该合成路线的关键步骤在于对次级烯丙基羟基相对于同烯丙基羟基的区域选择性保护。© 2002 Elsevier Science Ltd. 保留所有权利。
• BODENTEICH, MICHAEL;MARQUEZ, VICTOR E., TETRAHEDRON LETT., 30,(1989) N7, C. 4909-4912
  作者：BODENTEICH, MICHAEL、MARQUEZ, VICTOR E.

  DOI：——

  日期：——