phenyl 3,6-anhydro-β-D-glucopyranoside | 838086-83-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 3,6-anhydro-β-D-glucopyranoside
• 英文别名: (1R,3S,4R,5S,8R)-3-phenoxy-2,6-dioxabicyclo[3.2.1]octane-4,8-diol
• CAS: 838086-83-2
• 化学式: C₁₂H₁₄O₅
• 分子量: 238.24
• InChiKey: PWVWUTZTVVTPMQ-PZWNZHSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-(1,1′-联萘-2,2′-二氧)氯膦 、 phenyl 3,6-anhydro-β-D-glucopyranoside 在 吡啶 作用下， 以 甲苯 为溶剂， 以37%的产率得到2,4-bis{[(R(a))-1,1'-binaphthyl-2,2'-diyl]phosphite}-phenyl 3,6-anhydro-β-D-glucopyranoside
  参考文献：
  名称：

  单糖的吡喃糖苷骨架衍生的新型手性芳基二亚磷酸酯配体的合成及其在铜催化的二乙基锌与环烯酮的不对称共轭加成中的应用

  摘要：

  基于葡萄糖和半乳糖的吡喃糖苷主链，制备了新的手性芳基二亚磷酸酯配体。这些配体在具有高达88％ee的铜催化二乙基锌与环状烯酮的Cu催化不对称共轭加成中进行了测试。发现立体选择性取决于底物的环大小以及配体和铜源。对映选择性取决于配体主链的C-4立体定向中心的绝对构型，而对映选择性主要由亚萘基亚萘基的构型控制。

  DOI：

  10.1002/adsc.200404053
• 作为产物：
  描述：

  苯基-BETA-葡萄糖吡喃糖苷 在 sodium hydroxide 作用下， 以 吡啶 、 乙醇 为溶剂， 反应 2.0h， 生成 phenyl 3,6-anhydro-β-D-glucopyranoside
  参考文献：
  名称：

  单糖的吡喃糖苷骨架衍生的新型手性芳基二亚磷酸酯配体的合成及其在铜催化的二乙基锌与环烯酮的不对称共轭加成中的应用

  摘要：

  基于葡萄糖和半乳糖的吡喃糖苷主链，制备了新的手性芳基二亚磷酸酯配体。这些配体在具有高达88％ee的铜催化二乙基锌与环状烯酮的Cu催化不对称共轭加成中进行了测试。发现立体选择性取决于底物的环大小以及配体和铜源。对映选择性取决于配体主链的C-4立体定向中心的绝对构型，而对映选择性主要由亚萘基亚萘基的构型控制。

  DOI：

  10.1002/adsc.200404053

文献信息

• Synthesis of diphosphite ligands derived from glucopyranoside and their application in the Cu-catalyzed asymmetric 1,4-addition of organozinc to enones
  作者：Qing-Lu Zhao、Man Kin Tse、Lai-Lai Wang、Ai-Ping Xing、Xianxing Jiang

  DOI：10.1016/j.tetasy.2010.11.012

  日期：2010.12

  Novel chiral diphosphite ligands derived from glucopyranoside and H8-binaphthol were synthesized, and successfully employed in the Cu-catalyzed asymmetric 1,4-addition of organozinc reagents dimethylzinc, diethylzinc, and diphenylzinc to cyclic and acyclic enones with up to 96% ee. The stereochemically matched combination of d-glucopyranoside backbone and (R)-H8-binaphthyl in the ligand 2,4-bis[(R)-1

  合成了由吡喃吡喃糖苷和H 8-联萘酚衍生的新型手性二亚磷酸酯配体，并成功用于铜催化的有机锌试剂二甲基锌，二乙基锌和二苯基锌的不对称1,4-加成反应中，ee含量高达6％的环状和非环状烯酮。d-吡喃葡萄糖苷主链和配体2,4-双[（（R -1），1'-H 8）中的（R）-H 8-联萘的立体化学匹配组合-联萘基-2,2'-二基]亚磷酸}-苯基3,6-脱水-β-d-吡喃葡萄糖苷对诱导高对映选择性是必不可少的。观察到立体选择性对烯酮类型和环状烯酮环大小的显着依赖性。此外，产物对映异构的感觉主要取决于H 8-联萘基部分的构型。
• Enantioselective hydrogenation of functionalized olefins catalyzed by Rh-chiral bidentatephosphite complexes
  作者：Qing-Lu Zhao、Xiao Miao、Lai-Lai Wang

  DOI：10.1016/j.tetasy.2012.12.001

  日期：2013.2

  A novel catalytic system for the hydrogenation of dimethyl itaconate has been developed by using rhodium-diphosphite complexes. These chiral diphosphite ligands were derived from glucopyranoside, D-mannitol derivatives, and binaphthyl or H-8-binaphthyl phosphochloridites. The ligands based on the methyl 3,6-anhydro-alpha-D-glucopyranoside backbone and (R)- and (S)-binaphthol and/or (R)- and (S)-2,2'-dihydroxy-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthol gave almost complete conversion of the dimethyl itaconate and both enantiomers of dimethyl 2-methylsuccinate with excellent enantioselectivities. The stereochemically matched combination of methyl 3,6-anhydro-alpha-D-glucopyranoside and H-8-(S)-binaphthyl in ligand 2,4-bis[(S)-1,1'-H-8-binaphthyl-2,2'-diyl]-phosphite} methyl 3,6-anhydro-alpha-D-glucopyranoside was essential to afford dimethyl 2-methylsuccinate with up to 98% ee. The sense of the enantioselectivity of products was predominantly determined by the configuration of the biaryl moieties of the ligands. An initial screening of [Rh(cod)(2)]BF4 with these ligands in the hydrogenation of (E)-2-(3-butoxy-4-methoxybenzylidene)-3-methylbutanoic acid was carried out. Good enantioselectivity (75% ee) and low yield for (R)-2-(3-butoxy-4-methoxybenzyl)-3-methylbutanoic acid were obtained. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis of New Chiral Aryl Diphosphite Ligands Derived from Pyranoside Backbone of Monosacharides and Their Application in Copper-Catalyzed Asymmetric Conjugate Addition of Diethylzinc to Cyclic Enones
  作者：Lailai Wang、Yue-Ming Li、Chiu-wing Yip、Liqin Qiu、Zhongyuan Zhou、Albert S. C. Chan

  DOI：10.1002/adsc.200404053

  日期：2004.7

  New chiral aryl diphosphite ligands based on the pyranoside backbones of glucose and galactose were prepared. These ligands were tested in the Cu-catalyzed asymmetric conjugate addition of diethylzinc to cyclic enones with up to 88% ee. The stereoselectivity was found to be dependent on the ring size of the substrate as well as the ligand and copper source. The enantioselectivity depends on the absolute

  基于葡萄糖和半乳糖的吡喃糖苷主链，制备了新的手性芳基二亚磷酸酯配体。这些配体在具有高达88％ee的铜催化二乙基锌与环状烯酮的Cu催化不对称共轭加成中进行了测试。发现立体选择性取决于底物的环大小以及配体和铜源。对映选择性取决于配体主链的C-4立体定向中心的绝对构型，而对映选择性主要由亚萘基亚萘基的构型控制。