((2R,3S)-3-acetoxy-4,4-dimethyl-5-oxotetrahydrofuran-2-yl)methyl acetate | 104578-93-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ((2R,3S)-3-acetoxy-4,4-dimethyl-5-oxotetrahydrofuran-2-yl)methyl acetate
• 英文别名: [(2R,3S)-3-acetyloxy-4,4-dimethyl-5-oxooxolan-2-yl]methyl acetate
• CAS: 104578-93-0
• 化学式: C₁₁H₁₆O₆
• 分子量: 244.244
• InChiKey: NJEYUOOWELBJQT-RKDXNWHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (S)-3-[(R)-2,2-dimethyl[1,3]dioxolan-4-yl]-2,2-dimethyl-3-(trimethylsilanyloxy)propionic acid methyl ester 生成 ((2R,3S)-3-acetoxy-4,4-dimethyl-5-oxotetrahydrofuran-2-yl)methyl acetate
  参考文献：
  名称：

  O-甲硅烷基乙烯酮缩醛的化学性质；2,3-O-异亚丙基-D（和L）-甘油醛的非对映选择性Aldol反应导致2-脱氧-D（和L）-核糖

  摘要：

  2,3-O-异亚丙基-D（和L）-甘油醛（D和L-2）与乙烯酮甲硅烷基缩醛（1a，b）的非对映选择性碳-碳键形成反应在温和的乙腈中发生，得到相应的抗-β-甲硅烷氧基酯（D和L-3a）为主要产物，可以通过一些额外的步骤将其转化为2-脱氧-D（和L）-核糖。

  DOI：

  10.1016/s0040-4039(00)98924-x

文献信息

• L-Selectride-Mediated Highly Diastereoselective Asymmetric Reductive Aldol Reaction: Access to an Important Subunit for Bioactive Molecules
  作者：Arun K. Ghosh、Jorden Kass、David D. Anderson、Xiaoming Xu、Christine Marian

  DOI：10.1021/ol801971t

  日期：2008.11.6

  L-selectride reduction of a chiral or achiral enone followed by reaction of the resulting enolate with optically active alpha-alkoxy aldehydes proceeded with excellent diastereoselectivity. The resulting alpha,alpha-dimethyl-beta-hydroxy ketones are inherent to a variety of biologically active natural products.

  进行手性或非手性烯酮的L-selectride还原，然后使所得的烯醇化物与旋光性α-烷氧基醛反应，并具有极好的非对映选择性。所得的α，α-二甲基-β-羟基酮是多种生物活性天然产物所固有的。
• A General and Enantioselective Approach to Pentoses: A Rapid Synthesis of PSI-6130, the Nucleoside Core of Sofosbuvir
  作者：Manuel Peifer、Raphaëlle Berger、Valerie W. Shurtleff、Jay C. Conrad、David W. C. MacMillan

  DOI：10.1021/ja502205q

  日期：2014.4.23

  An efficient route towards biologically relevant pentose derivatives is described. The de novo synthetic strategy features an enantioselective alpha-oxidation reaction enabled by a chiral amine in conjunction with copper(II) catalysis. A subsequent Mukaiyama aldol coupling allows for the incorporation of a wide array of modular two-carbon fragments. Lactone intermediates accessed via this route provide a useful platform for elaboration, as demonstrated by the preparation of a variety of C-nucleosides and fluorinated pentoses. Finally, this work has facilitated expedient syntheses of pharmaceutically active compounds currently in clinical use.
• The chemistry of O-silylated ketene acetals. Stereocontrolled synthesis of 2-deoxy- and 2-deoxy-2-C-alkyl-erythro-pentoses
  作者：Yasuyuki Kita、Osamu Tamura、Fumio Itoh、Hitoshi Yasuda、Hiroko Kishino、Ya Yuan Ke、Yasumitsu Tamura

  DOI：10.1021/jo00238a015

  日期：1988.2
• KITA, YASUYUKI;TAMURA, OSAMU;ITOH, FUMIO;YASUDA, HITOSHI;KISHINO, HIROKO;+, J. ORG. CHEM., 53,(1988) N 3, 554-561
  作者：KITA, YASUYUKI、TAMURA, OSAMU、ITOH, FUMIO、YASUDA, HITOSHI、KISHINO, HIROKO、+

  DOI：——

  日期：——