1,2:5,6-di-O-isopropylidene-3-O-vinyl-α-D-glucofuranose | 6613-69-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2:5,6-di-O-isopropylidene-3-O-vinyl-α-D-glucofuranose
• 英文别名: 3-vinyl α-D-1,2:5,6-diisopropylidene glucofuranoside；O¹,O²;O⁵,O⁶-diisopropylidene-O³-vinyl-α-D-glucofuranose；O¹,O²;O⁵,O⁶-Diisopropyliden-O³-vinyl-α-D-glucofuranose；1,2:5,6-Di-O-isopropyliden-3-O-vinyl-α-D-glucofuranose；3-O-Vinyl-1,2:5,6-di-O-isopropyliden-α-D-glucose；(3aR,5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-ethenoxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• CAS: 6613-69-0
• 化学式: C₁₄H₂₂O₆
• 分子量: 286.325
• InChiKey: AOEFCYINIADJQF-RMPHRYRLSA-N

物化性质

• 沸点：
  115-116 °C(Press: 1.5-2.0 Torr)
• 密度：
  1.1710 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2:5,6-di-O-isopropylidene-3-O-vinyl-α-D-glucofuranose 在 sodium 作用下， 以 乙醚 、 氨 为溶剂， 生成 双丙酮葡萄糖
  参考文献：
  名称：

  Synthesis of β-lactams from sugar vinyl ethers and isocyanates

  摘要：

  DOI：

  10.1016/s0040-4039(01)93477-x
• 作为产物：
  描述：

  双丙酮葡萄糖 在 1,4-二氧六环 、 氢氧化钾 、 乙炔 作用下， 生成 1,2:5,6-di-O-isopropylidene-3-O-vinyl-α-D-glucofuranose
  参考文献：
  名称：

  Michant'ew; Lapenko, Zhurnal Obshchei Khimii, 1957, vol. 27, p. 2840; engl. Ausg. S. 2877

  摘要：

  DOI：

文献信息

• Three-Component Reaction between Vinyl Ethers, Secondary Phosphines, and Elemental Selenium: One-Pot Synthesis of 1-(Alkoxy)ethyl and 1-(Aryloxy)ethyl Phosphinodiselenoates
  作者：Boris Trofimov、Nina Gusarova、Alexander Artem’ev、Ludmila Oparina、Nikita Kolyvanov、Svetlana Malysheva、Oksana Vysotskaya

  DOI：10.1055/s-0031-1289655

  日期：2012.2

  aryl, etc.), were synthesized by means of a three-component reaction between the elemental selenium and the corresponding vinyl ether and secondary phosphine. The reaction proceeds readily in 1,4-dioxane at 90 ˚C for 1-1.5 hours and gives the phosphinodiselenoic esters quantitatively and in an entirely atom-economic manner. The reaction proceeds through electrophilic addition to the electron-rich

   借助于三组分合成了一个含有硒缩醛部分R 2 2 P（= Se）SeCH（Me）OR 1（R 1，R 2＝烷基，芳基等）的膦酸二亚硒酸酯系列。元素硒与相应的乙烯基醚和仲膦之间的反应。该反应可在90°C下于1,4-二恶烷中轻松进行1-1.5小时，并以完全原子经济的方式定量获得膦二亚硒酸酯。反应通过亲电加成到原位生成的膦二硒酸的富电子双键上进行。 膦-多组分反应-磷-硒-膦二硒酸酯
• Addition of secondary phosphines to a vinyl ether of diacetone-d-glucose: a new approach to optically active phosphines and their derivatives
  作者：Boris A. Trofimov、Boris G. Sukhov、Svetlana F. Malysheva、Natal’ya A. Belogorlova、Anatolii P. Tantsirev、Lidiya N. Parshina、Ludmila A. Oparina、Sergey P. Tunik、Nina K. Gusarova

  DOI：10.1016/j.tetlet.2004.09.172

  日期：2004.11

  Secondary phosphines react readily with a vinyl ether of diacetone-d-glucose under radical initiation conditions to give, in high yield, anti-Markovnikov adducts, diorganyl2-[3-O-(1,2:5,6-di-O-isopropylidene)-d-glucofuranosyloxy]ethyl}phosphines, which oxidize almost quantitatively upon reacting with air oxygen or elemental sulfur to form the corresponding optically active phosphine oxides or sulfides

  仲膦在自由基引发条件下容易与双丙酮-d-葡萄糖的乙烯基醚反应，以高收率得到反马氏化学加合物，二有机基2- [3- O -（（1,2：5,6-di- O-异亚丙基）-d-葡糖呋喃糖基氧基]乙基}膦，在与空气中的氧或元素硫反应形成相应的旋光性氧化膦或硫化物时，几乎被氧化。
• A New, General Method for the Synthesis of Carbasugar-Sugar Pseudodisaccharides
  作者：Kamyar Afarinkia、Mohamed Haji Abdullahi、Ian J. Scowen

  DOI：10.1021/ol901960y

  日期：2009.11.19

  A general synthetic methodology for the synthesis of sugar-carbasugar pseudodisaccharides is described. The methodology is based on the cycloaddition of pyran-2-ones to vinylated sugars and the subsequent manipulation of the cycloadducts to construct the carbasugar component of the pseudodisaccharide.

  描述了用于合成糖-碳水化合物假二糖的通用合成方法。该方法是基于吡喃-2-酮与乙烯基化糖的环加成反应，以及随后对环加合物的操纵以构建假二糖的羧化糖组分。
• Photocatalytic Defluorinative Three-Component Reaction of α-Trifluoromethyl Alkenes, Alkenes, and Sodium Sulfinates: Synthesis of Monofluorocyclopentenes
  作者：Weiyu Li、Xiaofei Chen、Lei Zhou

  DOI：10.1021/acs.orglett.2c02202

  日期：2022.8.19

  three-component reaction of α-trifluoromethyl alkenes, electron-rich alkenes, and sodium sulfinates for the synthesis of gem-difluoroalkenes in a radical/polar crossover manner was developed. Due to the strong electron-withdrawing nature of the sulfonyl group, the resultant gem-difluoroalkenes can be converted into various monofluorocyclopentenes via intramolecular base-mediated SNV reactions in one pot

  开发了 α-三氟甲基烯烃、富电子烯烃和亚磺酸钠的光催化三组分反应，以自由基/极性交叉方式合成偕二氟烯烃。由于磺酰基的强吸电子性质，所得到的偕二氟烯烃可以在一锅中通过分子内碱介导的 S N V 反应转化为各种单氟环戊烯。
• Asymmetric induction in [2+2]cycloaddition of chlorosulfonyl isocyanate to 1,2-O-isopropylidene-3-O-vinyl-glycofuranoses
  作者：Zbigniew Kałuża、Bartłomiej Furman、Madhumeeta Patel、Marek Chmielewski

  DOI：10.1016/s0957-4166(00)86293-x

  日期：1994.11

  The asymmetric [2+2]cycloaddition of chlorosulfonyl isocyanate to 1,2-O-isopropylidene-3-O-vinylglycofuranoses is presented. Bulky substituent at the C-4 carbon atom promotes excellent stereoselectivity affording (R) configuration at the C-4' carbon atom of the azetidinone ring. Intramolecular cyclization in compounds 9 or 12 provides diastereomeric cephem 20 and 21.