摩熵化学
数据库官网
小程序
打开微信扫一扫
首页 分子通 化学资讯 化学百科 反应查询 关于我们
请输入关键词

3,4,6-三-O-甲基-D-葡萄糖醛 | 16740-98-0

中文名称
3,4,6-三-O-甲基-D-葡萄糖醛
中文别名
——
英文名称
tri-O-methyl-D-glucal
英文别名
3,4,6-tri-O-methyl-D-glucal;(2R,3S,4R)-3,4-dimethoxy-2-(methoxymethyl)-3,4-dihydro-2H-pyran
3,4,6-三-O-甲基-D-葡萄糖醛化学式
CAS
16740-98-0
化学式
C9H16O4
mdl
——
分子量
188.224
InChiKey
PZJPNKKRMNFDQJ-HLTSFMKQSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 沸点:
    48-52 °C(Press: 0.01 Torr)
  • 密度:
    1.05±0.1 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    0.1
  • 重原子数:
    13
  • 可旋转键数:
    4
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    0.78
  • 拓扑面积:
    36.9
  • 氢给体数:
    0
  • 氢受体数:
    4

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    参考文献:
    名称:
    6-Oxomethylidenecyclohexa-2,4-diene-1-one衍生物与各种亲核试剂的产生和捕集的光解研究
    摘要:
    α-Oxoketenes和环己二烯α - oxoketenes是反应性的中间体,尤其是后者,由于它们的高再芳构化的潜力。在这篇通讯中,我们报告了从 4-OMe 和 4-OMOM 保护的间苯二酸二恶英产生此类物质的光解研究,以及它们的捕获以产生间苯二酸酯和酰胺,以及与烯醇-醚作为捕获试剂的加合物的形成。
    DOI:
    10.1002/hlca.202100189
  • 作为产物:
    描述:
    2,3,4,6-tetra-O-methyl-α-D-glucopyranosyl bromide 在 bis(cyclopentadienyl)-titanium(III) chloride 作用下, 以 四氢呋喃 为溶剂, 反应 0.25h, 以96%的产率得到3,4,6-三-O-甲基-D-葡萄糖醛
    参考文献:
    名称:
    Rapid Preparation of Variously Protected Glycals Using Titanium(III)
    摘要:
    Glycosyl chlorides and bromides can be rapidly converted to glycals in high yield by reaction with (Cp2Ti[III]Cl)(2). This reagent tolerates a wide range of common carbohydrate protecting groups, including silyl ethers, acetals, and esters; the methodology provides a general route for the preparation of glycals substituted with both acid- and base-labile functionality. A reaction mechanism is proposed that is based on heteroatom abstraction to give an intermediate glycosyl radical. This radical reacts with a second equivalent of Ti(III) to yield a glycosyltitanium(IV) species. P-Heteroatom elimination from the glycosyltitanium(IV) complex gives the glycal.
    DOI:
    10.1021/jo982447k
  • 作为试剂:
    参考文献:
    名称:
    6-Oxomethylidenecyclohexa-2,4-diene-1-one衍生物与各种亲核试剂的产生和捕集的光解研究
    摘要:
    α-Oxoketenes和环己二烯α - oxoketenes是反应性的中间体,尤其是后者,由于它们的高再芳构化的潜力。在这篇通讯中,我们报告了从 4-OMe 和 4-OMOM 保护的间苯二酸二恶英产生此类物质的光解研究,以及它们的捕获以产生间苯二酸酯和酰胺,以及与烯醇-醚作为捕获试剂的加合物的形成。
    DOI:
    10.1002/hlca.202100189
点击查看最新优质反应信息

文献信息

  • Rhodium-Catalyzed Denitrogenative Transannulation of <i>N</i>-Sulfonyl-1,2,3-triazoles with Glycals Giving Pyrroline-Fused <i>N</i>-Glycosides
    作者:Jingjing Bi、Qiang Tan、Hao Wu、Qingfeng Liu、Guisheng Zhang
    DOI:10.1021/acs.orglett.1c02141
    日期:2021.8.20
    with exclusive regioselectivity and stereoselectivity. Functional application of such a resultant product by oxidative addition and epoxidation is also explored. Notably, the treatment of a pyrroline-fused N-glycoside (3a) with TMSOTf efficiently leads to an interesting unexpected C-nucleoside (9) via a TMSOTf-inducing ring opening/acetyl migration/ring closing reaction sequence.
    这里描述的是通过催化的N-磺酰基-1,2,3-三唑与聚糖的脱氮环化反应选择性合成 2,3-二氢吡咯稠合的N-糖苷。一系列吡咯啉稠合的N-糖苷以中等至极好的收率提供,具有独特的区域选择性和立体选择性。还探索了这种通过氧化加成和环氧化得到的产物的功能应用。值得注意的是,通过 TMSOTf 诱导的开环/乙酰基迁移/闭环反应序列,用 TMSOTf处理吡咯啉稠合的N-糖苷(3a)有效地导致有趣的意外C-核苷(9)。
  • Highly Stereoselective Synthesis of 2,3-Unsaturated Thioglycopyranosides Employing Molecular Iodine
    作者:Basi Reddy、Ch. Divyavani、Jhillu Yadav
    DOI:10.1055/s-0029-1218722
    日期:2010.5
    Molecular iodine has been utilized for the first time for the thioglycosidation of d-glycals with various thiols to afford the corresponding 2,3-unsaturated thioglycosides in high yields. In the case of tri-O-acetyl-d-glucal, the α-anomer was obtained exclusively. The use of readily available iodine makes this method quite simple, more convenient, and practical.
    首次利用分子实现了d-甘露二糖糖类代糖基化反应,与各种醇反应以高产率得到相应的2,3-不饱和代糖苷。在三-O-乙酰基-d-甘露二糖糖类的情况下,仅获得了α-异构体。由于使用了易获得的,这种方法非常简单、便捷且实用。
  • InBr3-Catalyzed Ferrier Rearrangement: An Efficient Synthesis of C-Pseudoglycals
    作者:J. S. Yadav、B. V. Subba Reddy
    DOI:10.1055/s-2002-20968
    日期:——
    Glycals react smoothly with silyl nucleophiles such as allyltrimethylsilane, trimethylsilyl cyanide and trimethylsilyl azide in the presence of a catalytic amount of indium tribromide to give the corresponding 2,3-unsaturated allyl glycosides, glycosyl cyanides and glycosyl azides in excellent yields with high α-selectivity.
    在三的催化作用下,甘露糖碳酰化合物能够与甲硅烷类亲核试剂如烯丙基三甲基硅烷、三甲基和三甲基叠氮顺利反应,以优异的产率和高α-选择性得到相应的2,3-不饱和烯丙基糖苷、糖基化物和糖基叠氮
  • Copper mediated iodoacetoxylation and glycosylation: effective and convenient approaches for the stereoselective synthesis of 2-deoxy-2-iodo glycosides
    作者:Suresh Kumar Battina、Sudhir Kashyap
    DOI:10.1016/j.tetlet.2016.01.035
    日期:2016.2
    Copper(II) triflate catalyzed stereoselective glycosylation of 2-iodo-glycosyl acetate donor is reported. Anomeric activation of 2-deoxy-1-O-acetyl sugar employing Cu(OTf)2 found to be an attractive as well effective alternative reagent to the most frequently used triflic acid (TfOH) source such as TMSOTf or TBSOTf. Scope of the reaction was explored for various aglycones. This protocol involves simple
    报道了三氟甲磺酸(II)催化2--糖基乙酸乙酸酯供体的立体选择性糖基化。发现使用Cu(OTf)2的2-脱氧-1- O-乙酰基糖的端基活化是最常用的三氟甲磺酸(TfOH)来源(如TMSOTf或TBSOTf)的诱人且有效的替代试剂。探索了各种糖苷配基的反应范围。该方案涉及简单的反应操作,采用较便宜且无毒的试剂系统,并且能够立体选择性地制备2-脱氧-2--糖苷。此外,CuI / NaIO 4在环境温度下在AcOH的存在下促进了各种糖类的区域选择性乙酰氧基化,从而获得了2--糖基乙酸酯。
  • Stereoselective Synthesis of 2‐Deoxyglycosides from Glycals by Visible‐Light‐Induced Photoacid Catalysis
    作者:Gaoyuan Zhao、Ting Wang
    DOI:10.1002/anie.201800909
    日期:2018.5.22
    The direct, photoacid‐catalyzed synthesis of 2‐deoxyglycosides from glycals is reported. A series of phenol‐conjugated acridinium‐based organic photoacids were rationally designed, synthesized, and studied alongside the commercially available phenolic catalyst eosin Y. In the presence of such a photoacid catalyst and light, synthetic glycals were activated and coupled with a range of alcohols to afford
    据报道,由糖类直接,光酸催化合成了2-脱氧糖苷。与市售的催化剂曙红Y一起,合理设计,合成和研究了一系列基于共轭啶基的有机光酸。在这种光酸催化剂和光的存在下,合成糖被活化并与多种醇偶联以高收率和优异的α-选择性提供2-脱氧糖苷。
查看更多