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(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)-(1→6)1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

中文名称
——
中文别名
——
英文名称
(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)-(1→6)1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
英文别名
(1S,2R,6R,8R,9S)-8-[[(2R,3R,4R,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolan-2-yl]oxymethyl]-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecane
(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)-(1→6)1,2:3,4-di-O-isopropylidene-α-D-galactopyranose化学式
CAS
——
化学式
C38H46O10
mdl
——
分子量
662.777
InChiKey
RQZUAHVJYGUVII-OEWIAOAZSA-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

计算性质

  • 辛醇/水分配系数(LogP):
    4.5
  • 重原子数:
    48
  • 可旋转键数:
    13
  • 环数:
    7.0
  • sp3杂化的碳原子比例:
    0.53
  • 拓扑面积:
    92.3
  • 氢给体数:
    0
  • 氢受体数:
    10

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

反应信息

点击查看最新优质反应信息

文献信息

  • Stereoselective 1,2-<i>cis</i> Furanosylations Catalyzed by Phenanthroline
    作者:Hengfu Xu、Richard N. Schaugaard、Jiayi Li、H. Bernhard Schlegel、Hien M. Nguyen
    DOI:10.1021/jacs.2c02063
    日期:2022.4.27
    furanosylation method promoted by phenanthroline catalysts under mild and operationally simple conditions. NMR experiments and density functional theory calculations support an associative mechanism in which the rate-determining step occurs from an inverted displacement of the faster-reacting phenanthrolinium ion intermediate with an alcohol nucleophile. The phenanthroline catalysis system is applicable
    1,2-顺式呋喃糖苷键的立体选择性形成,许多生物学相关的寡糖多糖的基序,仍然是一个重要的合成挑战。我们在此报告了一种由咯啉催化剂在温和且操作简单的条件下促进的新立体选择性 1,2-顺式呋喃基化方法。NMR 实验和密度泛函理论计算支持一种关联机制,其中速率决定步骤发生在反应较快的咯啉离子中间体与醇亲核试剂的反向置换中。咯啉催化系统适用于许多呋喃糖基供体,以提供具有挑战性的 1,2-顺式具有高异头异构体选择性的高产率取代产物。虽然阿拉伯呋喃糖基提供 β-1,2-顺式产品,但木糖呋喃核糖有利于 α-1,2-顺式产品。
  • Catalytic Stereoselective 1,2-<i>cis</i>-Furanosylations Enabled by Enynal-Derived Copper Carbenes
    作者:Bidhan Ghosh、Adam Alber、Chance W. Lander、Yihan Shao、Kenneth M. Nicholas、Indrajeet Sharma
    DOI:10.1021/acscatal.3c05237
    日期:2024.1.19
    and their stereoselective synthesis remains a significant challenge. In this vein, we have developed a stereoselective approach to 1,2-cis-furanosylations using earth-abundant copper catalysis. This protocol proceeds under mild conditions at room temperature and employs readily accessible benchtop stable enynal-derived furanose donors. This chemistry accommodates a variety of alcohols, including primary
    1,2-顺式呋喃糖苷存在于各种生物医学相关糖苷中,其立体选择性合成仍然是一个重大挑战。本着这一精神,我们开发了一种利用地球上丰富的催化进行 1,2-顺式-呋喃基化的立体选择性方法。该方案在室温温和条件下进行,并采用易于获得的台式稳定烯醛衍生呋喃糖供体。这种化学反应适用于多种醇,包括伯醇、仲醇和叔醇,以及甘露糖醇受体,这些醇与大多数已知的呋喃糖基化方法不相容。所得 1,2-顺式- 呋喃糖苷产品对核糖阿拉伯糖系列均表现出高产率和异头选择性。此外,异头选择性与C2氧保护基团和起始供体的异头构型无关。实验证据和计算研究支持我们的假设,即呋喃糖供体的 C2 氧与进入的醇亲核试剂之间的螯合是观察到的 1,2-顺式立体选择性的原因。
  • Stereospecific Furanosylations Catalyzed by Bis-thiourea Hydrogen-Bond Donors
    作者:Andrew B. Mayfield、Jan B. Metternich、Adam H. Trotta、Eric N. Jacobsen
    DOI:10.1021/jacs.0c00335
    日期:2020.2.26
    We report a new method for stereoselective O-furanosylation reactions promoted by a precisely tailored bis-thiourea hydrogen-bond-donor catalyst. Furanosyl donors outfitted with an anomeric dialkylphosphate leaving group undergo substitution with high anomeric selectivity, providing access to the challenging 1,2-cis substitution pattern with a range of alcohol acceptors. A variety of stereochemically distinct, benzyl-protected glycosyl donors were engaged successfully as substrates. Mechanistic studies support a stereospecific mechanism in which rate-determining substitution occurs from a catalyst-donor resting-state complex.
  • Studies on the synthesis of 1,2-cis pentofuranosides from S-glycofuranosyl dithiocarbamates, dithiocarbonates and phosphorodithioates
    作者:Jadwiga Bogusiak、Wiesław Szeja
    DOI:10.1016/s0008-6215(00)00220-2
    日期:2001.1
    The selectivity in the synthesis of 1,2-cis glycofuranosides from dithiocarbonates, dithiocarbamates and phosphorodithioates is improved by combined use of silver triflate and catalytic amount of hexamethylphosphoramide (HMPA) under mild conditions. (C) 2001 Elsevier Science Ltd. All rights reserved.
  • Yokoyama, Yasuo; Hanamoto, Takeshi; Jin, Xiu Lan, Heterocycles, 2000, vol. 52, # 3, p. 1203 - 1206
    作者:Yokoyama, Yasuo、Hanamoto, Takeshi、Jin, Xiu Lan、Jin, Yong Zhi、Inanaga, Junji
    DOI:——
    日期:——
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