2-propynyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside | 121237-62-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2-propynyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
• 英文别名: ((2R,3S,6S)-3-acetoxy-6-(prop-2-yn-1-yloxy)-3,6-dihydro-2H-pyran-2-yl)methyl acetate；2'-propyn-1'-yl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside；2'-propyn-1'-yl4, 6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside；2-(prop-2-ynyl)-4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside；prop-2-yn-1-yl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside；2-propyn-1-yl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside；2-[(acetyloxy)methyl]-6-(2-propynyloxy)-3,6-dihydro-2H-pyran-3-yl acetate；[(2R,3S,6S)-3-acetyloxy-6-prop-2-ynoxy-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 121237-62-5
• 化学式: C₁₃H₁₆O₆
• 分子量: 268.266
• InChiKey: IUPPZLJWDOLLRS-XQQFMLRXSA-N

物化性质

• 熔点：
  72-74 °C
• 沸点：
  363.6±42.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 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：

  2-propynyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 在 platinum(II) chloride 吡啶 作用下， 以 甲苯 为溶剂， 生成 Triacetyl-D-pseudoglucal
  参考文献：
  名称：

  Enyne Metathesis on Prop-2-ynyl-2,3-dideoxy-α-d-erythro-hex-2-enopyranosides

  摘要：

  首次对不同官能化的丙-2-炔基-2,3-二脱氧-α-d-赤型-己-2-烯吡喃糖苷（1、2和3）的烯炔易位反应进行了分析，现将其新颖且有趣的结果描述如下。

  DOI：

  10.1055/s-2001-13352
• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 在 copper(ll) sulfate pentahydrate 、 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 1.55h， 生成 2-propynyl 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）。
• A Highly Efficient Magnetic Iron(III) Nanocatalyst for Ferrier Rearrangements
  作者：Youxian Dong、Zekun Ding、Hong Guo、Le Zhou、Nan Jiang、Heshan Chen、Saifeng Qiu、Xiaoxia Xu、Jianbo Zhang

  DOI：10.1055/s-0037-1611855

  日期：2019.7

  A novel and highly efficient magnetic Fe3O4@C@Fe(III) core–shell catalyst, in which the carbon shell was prepared from lotus leaf, was fabricated. This nanocatalyst was successfully applied in the synthesis of a series of 2,3-unsaturated O-glycosides in excellent yields and with high selectivity, especially in the case of 2-halo O-glycosides, which differ in reactivity from nonsubstituted O-glycosides

  制备了一种新型高效的磁性 Fe3O4@C@Fe(III) 核壳催化剂，其中碳壳由荷叶制备。该纳米催化剂成功地应用于合成一系列 2,3-不饱和 O-糖苷，收率高，选择性高，特别是在反应性与未取代 O-糖苷不同的 2-卤代 O-糖苷的情况下，但以前几乎没有探索过。此外，通过施加外部磁力，催化剂可以很容易地从反应中分离出来，并且至少重复使用五次，而不会显着降低产品的产率。此外，该反应在克级规模上很容易进行，这为未来的应用提供了广阔的前景。
• Ferrier Rearrangement Catalyzed by HClO₄-SiO₂: Synthesis of 2,3-Unsaturated Glycopyranosides
  作者：Anup Kumar Misra、Pallavi Tiwari、Geetanjali Agnihotri

  DOI：10.1055/s-2004-837297

  日期：——

  Alkyl 2,3-unsaturated glycopyranosides have been prepared by the Ferrier rearrangement of acetyl protected glycals catalyzed by HClO 4 -SiO 2 . Operational simplicity, use of economically convenient catalyst, mild reaction conditions, high yields, short reaction times are the key features of this protocol.

  已通过 HClO 4 -SiO 2 催化乙酰保护糖基的 Ferrier 重排制备烷基 2,3-不饱和吡喃糖苷。操作简单、使用经济上方便的催化剂、温和的反应条件、高收率、短反应时间是该协议的主要特点。
• Bi(OTf)3 and SiO2-Bi(OTf)3 as Effective Catalysts for the Ferrier Rearrangement#
  作者：J. Babu、A. Khare、Y. Vankar

  DOI：10.3390/10080884

  日期：——

  Bi(OTf)3 and SiO2-Bi(OTf)3 are found to effectively catalyze the Ferrierrearrangement of tri-O-acetyl glycals with different alcohols providing an effective routeto 2,3-unsaturated O-glycosides with good anomeric selectivity and good to excellentyields after short reaction times.

  经发现，Bi(OTf)3 和 SiO2-Bi(OTf)3 能有效催化三-O-乙酰基糖类的Ferrier重排反应，在不同的醇作用下，提供了一条有效合成2,3-不饱和O-糖苷的途径，具有良好的异头选择性和良好的至极佳的产率，且反应时间短。
• Magnetic Core-Shell Fe3O4@C-SO3H as an Efficient and Renewable ‘Green Catalyst’ for the Synthesis of O-2,3-Unsaturated Glycopyranosides
  作者：Jianbo Zhang、Guosheng Sun、Saifeng Qiu、Zekun Ding、Heshan Chen、Jiafen Zhou、Zhongfu Wang

  DOI：10.1055/s-0036-1588891

  日期：——

  rearrangement. The donors include 3,4,6-tri-O-acetyl- d -glucal and 3,4-di-O-acetyl- l -rhamnal. The acceptors consist of primary alcohols, secondary alcohols, tert-butanol, unsaturated alcohols, halogenated alcohol, sterol, sugars, and phenols. O-2,3-Unsaturated glycosides were obtained rapidly ( 5:1 to 19:1). Moreover, the catalyst can be easily separated from the reaction with an external magnetic force

  研究了一种磁性核壳固体酸催化剂 Fe3O4@C-SO3H，用于通过费里叶重排合成 O-2,3-不饱和糖苷。供体包括3,4,6-三-O-乙酰-d-葡糖醛和3,4-二-O-乙酰-1-鼠李醛。受体由伯醇、仲醇、叔丁醇、不饱和醇、卤代醇、甾醇、糖和酚组成。快速获得 O-2,3-不饱和糖苷（5:1 至 19:1）。此外，该催化剂可以很容易地通过外部磁力从反应中分离出来并重复使用至少 5 次，每次循环后产物的产率没有任何显着下降，表明它是一种很有前途的 2,3-不饱和绿色催化剂。糖苷合成。