n-propyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside | 23339-22-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: n-propyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
• 英文别名: Propyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside；[(2R,3S,6S)-3-acetyloxy-6-propoxy-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 23339-22-2
• 化学式: C₁₃H₂₀O₆
• 分子量: 272.298
• InChiKey: ZKNHSVYHUUYOPH-XQQFMLRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  n-propyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 在 咪唑 、 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 propyl 6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
  参考文献：
  名称：

  Stereocontrolled palladium(0)-catalyzed preparation of unsaturated azidosugars: an easy access to 2- and 4-aminoglycosides

  摘要：

  The palladium-catalyzed substitution of alkyl 4,6-di-O-acetyl-alpha-D-erythro-hex-2-eno-pyranosides using NaN3 as the nucleophile gave predominantly the corresponding alkyl 2-azido-2,3,4-trideoxy-alpha-D-threo-hex-2-enopyranosides in the presence of Pd(PPh3)(4). However, alkyl 6-O-acetyl-4-azido-2,3,4-trideoxy-alpha-D-erythro-hex-2-enopyranosi des were obtained as the major products using Pd(PPh3)4 as the catalyst in the presence of dppb as the added ligand. Conversely, alkyl 6-O-(tert-butyidimethylsilyl)-4-0-methoxycarbonyl-2,3-dideoxy-alpha-D-hex-2-enopyranosides gave exclusively alkyl 4-azido-6-O-(tert-butyldimethylsilyi)-2,3,4-trideoxy-alpha-D-erythro-hex-2-enopyranosides in the presence of Pd-2(dba)(3)/PPh3 as the catalyst and Me3SiN3 as the nucleophile. The bis-hydroxylation followed by hydrogenation of ethyl 4-azido-2,3,4-trideoxy-alpha-D-erythro-hex-2-enopyranoside afforded the corresponding 4-amino-alpha-D-mannopyranoside, when propyl 2-azido-2,3,4-trideoxy-alpha-D-threo-hex-3-enopyranoside gave the 2-amino-alpha-D-altropyranoside under the same conditions. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.06.041
• 作为产物：
  描述：

  3'-bromopropyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 、 苯 为溶剂， 反应 12.0h， 以77%的产率得到n-propyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
  参考文献：
  名称：

  Catalytic tin radical mediated tricyclisations. Part 1. Monocyclisation studies †

  摘要：

  提出了一种催化锡自由基介导的自由基级联反应的一般策略，其中在一步中构建了三个环。三环化过程的初始步骤是使用在1-O和/或4-O位具有不饱和取代基的2,3-脱氧-α-D-赤藓糖亨糖醛进行研究。用于1-O位取代基环化的底物是通过一种新型的氯化锌催化的Ferrier重排反应，将三-O-乙酰化的D-葡糖醛与不饱和醇反应而制备的，而用于4-O位取代基环化的底物则是通过烷基化或酰基化反应，对乙基6-O-保护的2,3-脱氧-α-D-赤藓糖亨糖醛进行处理。丙炔基取代基能有效环化，但丙烯基取代基则较差。丙炔酰基取代基在没有环化的情况下经历了氢锡化反应。

  DOI：

  10.1039/b000661k

文献信息

• Robust perfluorophenylboronic acid-catalyzed stereoselective synthesis of 2,3-unsaturated <i>O</i>-, <i>C</i>-, <i>N</i>- and <i>S</i>-linked glycosides
  作者：Madhu Babu Tatina、Xia Mengxin、Rao Peilin、Zaher M A Judeh

  DOI：10.3762/bjoc.15.125

  日期：——

  A convenient protocol was developed for the synthesis of 2,3-unsaturated C-, O-, N- and S-linked glycosides (enosides) using 20 mol % perflurophenylboronic acid catalyst via Ferrier rearrangement. Using this protocol, D-glucals and L-rhamnals reacted with various C-, O-, N- and S-nucleophiles to give a wide range of glycosides in up to 98% yields with mainly α-anomeric selectivity. The perflurophenylboronic

  开发了一种方便的方案，用于使用20摩尔％的全氟苯基硼酸催化剂通过Ferrier重排合成2，3-不饱和C-，O-，N-和S-连接的糖苷（烯醇）。使用该方案，D-葡糖醛酸和L-鼠李糖醛与各种C-，O-，N-和S-亲核试剂反应，以高达98％的收率（主要是α-异头异构体选择性）提供各种糖苷。全氟苯基硼酸在非常温和的反应条件下成功催化了多种底物（葡糖醛和亲核试剂）。
• 3,5-Dinitrobenzoic acid catalyzed synthesis of 2,3-unsaturated O- and S-glycosides and tetrahydropyranylation of alcohols and phenols
  作者：Naganjaneyulu Bodipati、Srinivasa Rao Palla、Venkateshwarlu Komera、Rama Krishna Peddinti

  DOI：10.1016/j.tetlet.2014.10.093

  日期：2014.12

  A simple procedure for the synthesis of 2,3-unsaturated glycosides in acetonitrile and tetrahydropyranylation of alcohols and phenols in dichloromethane in the presence of 3,5-dinitrobenzoic acid is described. A variety of alcohols and thiols are reacted with glycals to give the desired products in high yields with high α-selectivity.

  描述了一种简单的程序，用于在乙腈中合成2,3-不饱和糖苷以及在3,5-二硝基苯甲酸存在下在二氯甲烷中将醇和酚进行四氢吡喃基化。使多种醇和硫醇与缩醛反应，以高收率和高α选择性得到所需产物。
• A Facile H2SO4/4 Å Molecular Sieves Catalyzed Synthesis of 2,3-Unsaturated O-Glycosides via Ferrier-Type Rearrangement
  作者：Jianbo Zhang、Jiafen Zhou、Bo Zhang、Guofang Yang、Xuan Chen、Qingbing Wang、Zhongfu Wang、Jie Tang

  DOI：10.1055/s-0029-1219539

  日期：2010.4

  A novel method for synthesizing 2,3-unsaturated glycosides has been developed using a metal-free catalytic system. This catalyst, sulfuric acid/4 Šmolecular sieves can catalyze the reaction of 3,4,6-tri-O-acetyl-d-glucals and a wide range of alcohols at room temperature, affording 2,3-unsaturated glycosides in good α-selectivity (α/β > 6:1) via a Ferrier-type rearrangement.

  开发了一种无金属催化体系的新方法来合成2,3-不饱和糖苷。这种催化剂，即硫酸/4 Å分子筛，可以在室温下催化3,4,6-三-O-乙酰基-d-葡醛酸与多种醇的反应，通过Ferrier型重排得到高α-选择性（α/β > 6:1）的2,3-不饱和糖苷。
• [EN] TRANSACETALISATION PROCESS<br/>[FR] METHODE DE TRANSACETALISATION
  申请人：UNIV MONASH

  公开号：WO2005070911A1

  公开（公告）日：2005-08-04

  The invention relates to the resolution of racemic mixtures, and in particular to the separation of enantiomers of chiral alcohols utilising recyclable chiral auxiliaries. The present invention also relates to a process for preparing these recyclable chiral auxiliaries using an enantiomerically pure alcohol.

  这项发明涉及手性混合物的分离，特别是利用可回收手性辅助剂分离手性醇的对映体。本发明还涉及利用对映纯醇制备这些可回收手性辅助剂的方法。
• H2SO4-SiO2: Highly efficient and novel catalyst for the Ferrier-type glycosylation
  作者：Jia Fen Zhou、Xuan Chen、Qing Bing Wang、Bo Zhang、Li Yan Zhang、Abdullah Yusulf、Zhong Fu Wang、Jian Bo Zhang、Jie Tang

  DOI：10.1016/j.cclet.2010.03.013

  日期：2010.8

  Sulfuric acid immobilized on silica gel is designed as a very useful catalyst for synthesis of 2,3-unsaturated glycopyranosides. This handy, metal-free, environment friendly transformation provides high yields and α-stereoselectivities in a very few amount (<0.02 eq.) of catalyst and in short reaction times (<10 min).

  固定在硅胶上的硫酸被设计为非常有用的合成2，3-不饱和糖吡喃糖苷的催化剂。这种方便，无金属，环境友好的转化方法，只需极少量的催化剂（<0.02 eq。）和较短的反应时间（<10分钟），即可提供高收率和α-立体选择性。