n-propyl 4,6-di-O-acetyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranoside | 1400767-38-5

• 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-β-D-erythro-hex-2-enopyranoside
• 英文别名: propyl 4,6-di-O-acetyl-2,3-dideoxy-β-D-erythrohex-2-enopyranoside
• CAS: 1400767-38-5
• 化学式: C₁₃H₂₀O₆
• 分子量: 272.298
• InChiKey: ZKNHSVYHUUYOPH-YNEHKIRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.19
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  D-葡萄糖 在 copper(ll) sulfate pentahydrate 、 氢溴酸 、 sodium acetate 、 四氯化碲 、 溶剂黄146 、 锌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.67h， 生成 n-propyl 4,6-di-O-acetyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranoside 、 n-propyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
  参考文献：
  名称：

  Stereoselective synthesis of pseudoglycosides catalyzed by TeCl4 under mild conditions

  摘要：

  Catalytic amounts of tellurium(IV) tetrachloride were used to promote the O-glycosylation of 3,4,6-tri-O-acetyl-D-glucal to give the corresponding 2,3-unsaturated-O-glycosides. With simple alcohols, the desired compounds were obtained in good yields and excellent anomeric selectivity in a short reaction time using only 2 mol % of the catalyst. The application of the method in the synthesis of a small set of glycopyranosides with rigid or flexible linkers gave the corresponding a anomers as products in good yields. Further applications of some of the synthesized compounds in allylation reaction of aldehydes gave the corresponding homoallylic alcohols in good yields. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.09.073

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。
• 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。
• Structure-based design, synthesis and antitumoral evaluation of enulosides
  作者：Jonh A.M. Santos、Cosme S. Santos、Claudia L.A. Almeida、Thiago D.S. Silva、João R. Freitas Filho、Gardenia C.G. Militão、Teresinha G. da Silva、Carlos H.B. da Cruz、Juliano C.R. Freitas、Paulo H. Menezes

  DOI：10.1016/j.ejmech.2017.01.036

  日期：2017.3

  Enulosides, carbohydrate derivatives containing an alpha,beta-unsaturated carbonyl unit, were designed and obtained in high yields and isomeric purity. All synthesized compounds exhibited antitumoral activity in micromolar range against four tested tumor cells lines, being the best results observed for HL-60 cells. These compounds open new possibilities to prepare an array of more active, site-specific or selective antitumor agents. (C) 2017 Elsevier Masson SAS. All rights reserved.