methyl 2,3,4-tri-O-benzoyl-6-thio-α-D-glucopyranoside | 686341-49-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-benzoyl-6-thio-α-D-glucopyranoside
• 英文别名: [(2S,3S,4S,5R,6S)-4,5-dibenzoyloxy-6-methoxy-2-(sulfanylmethyl)oxan-3-yl] benzoate
• CAS: 686341-49-1
• 化学式: C₂₈H₂₆O₈S
• 分子量: 522.576
• InChiKey: OZQLQZDCXVYDHC-NRUNVSGISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  98.4
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-benzoyl-6-thio-α-D-glucopyranoside 在 三乙胺 、 copper(ll) bromide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 19.0h， 生成 (2S,3S,4S,5R,6S)-2-(((1H-indol-3-yl)thio)methyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triyltri benzoate
  参考文献：
  名称：

  铜催化的吲哚与 N-(硫代糖苷)琥珀酰亚胺的 C2-或 C3-硫糖基化反应：一种有效的全合成靛蓝靛蓝苷的策略

  摘要：

  Isatindigotindolosides 是一种在 C2 位含有 1 - S -β-吡喃葡萄糖基单元的吲哚，具有良好的生物活性。在这里，我们报告了铜催化的吲哚 C2- 或 C3- 硫糖基化与N -(硫代糖苷) 琥珀酰亚胺构建吲哚生物碱糖苷。该反应对官能团具有广泛的耐受性，因为各种吲哚和硫糖苷都是合适的。它还提供了一种可靠的方法来对天然产物（例如禾本科和褪黑激素）进行后期修饰。以 C2-硫糖基化反应为关键步骤，成功完成了靛蓝靛蓝苷I和II的全合成。

  DOI：

  10.1021/acs.orglett.2c04270
• 作为产物：
  描述：

  甲基2,3,4-三-O-苯甲酰-α-D-吡喃葡萄糖苷 在 一水合肼 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.67h， 生成 methyl 2,3,4-tri-O-benzoyl-6-thio-α-D-glucopyranoside
  参考文献：
  名称：

  Rhenium(V)-Catalyzed Synthesis of 2-Deoxy-α-glycosides

  摘要：

  A mild method for the synthesis of 2-deoxysugars from the coupling of glycals with a range of nucleophiles is described. The method employs 1 mol % of an air- and moisture-tolerant rhenium-oxo complex [ReOCl3(SMe2)(Ph3PO)] as a catalyst for the formation of O-, N-, and S-alpha-glycosides. The catalytic system tolerates a number of commonly employed protecting groups, including isopropylidene acetals, alkyl and silyl ethers, acetates, and benzoates. Furthermore, the high-oxidation-state complex selectively catalyzes the coupling with the glycal acceptor in preference to oxidation of the glycals, alcohols, and even thiols.

  DOI：

  10.1021/ja031895t

文献信息

• Synthesis of non-glycosidic 4,6′-thioether-linked disaccharides as hydrolytically stable glycomimetics
  作者：María Laura Uhrig、László Szilágyi、Katalin E. Kövér、Oscar Varela

  DOI：10.1016/j.carres.2007.03.025

  日期：2007.9

  of the protecting groups of 8 by acid hydrolysis, formation of an 1,6-anhydro bridge was observed in the 3-deoxy-4-thiohexopyranose unit (10). The free non-glycosidic thioether-linked disaccharide 3-deoxy-4-S-(6-deoxy-alpha,beta-D-galactopyranos-6-yl)-4-thio-alpha,beta-D-xylo-h exopyranose (11) was obtained by acetolysis of 10 followed by O-deacetylation. A similar sequence starting from the enone

  将1,2：3,4-二-O-异亚丙基-6-硫代-α-D-半乳糖（2）迈克尔加成至2-丙基6-O-乙酰基-3,4-二脱氧-α-D-甘油-hex-3-enopyranosid-2-ulose（1）作为主要的非对映异构体，提供了2-丙基6-O-乙酰基-3-脱氧-4-S-（6-脱氧-1,2：3,4-二-O-异亚丙基-α-D-吡喃并吡喃半乳糖s-6-基）-4-硫代α-D-苏-吡喃并吡喃糖苷-2-果糖（3，产率91％）。还原3的羰基，然后进行O-脱乙酰基处理，以1：2的比例得到两个差向异构体7（α-D-lyxo）和8（α-D-xylo）。通过酸水解除去8的保护基时，在3-脱氧-4-硫代己吡喃糖单元（10）中观察到1，6-脱水桥的形成。游离的非糖苷硫醚连接的二糖3-deoxy-4-S-（6-deoxy-alpha，beta-D-galactopyranos-6-yl）-4-thio-alpha，β-D-x
• Two Straightforward Strategies for the Synthesis of Thiodisaccharides with a Furanose Unit as the Nonreducing End
  作者：Evangelina Repetto、Carla Marino、M. Laura Uhrig、Oscar Varela

  DOI：10.1002/ejoc.200700874

  日期：2008.1

  Thiodisaccharides having a 1-thiopentofuranose nonreducing end were synthesized by two routes starting from per-O-acylaldofuranoses with arabino, ribo, and xylo configurations. These glycosyl donors were converted into S-glycosyl isothiourea derivatives as precursors of 1-thiofuranose units, which were generated in situ and trapped by a sugar enone to produce, by Michael addition, the thioglycosidic

  具有 1-硫代戊呋喃糖非还原性末端的硫代二糖是通过两种途径合成的，从具有阿拉伯、核糖和木糖构型的 per-O-酰基醛基呋喃糖开始。这些糖基供体被转化为 S-糖基异硫脲衍生物作为 1-硫代呋喃糖单元的前体，其原位生成并被糖烯酮捕获，通过迈克尔加成产生硫糖苷键。或者，MoO2Cl2 促进的 6-硫糖衍生物的硫醇基团由过氧酰基呋喃糖进行糖基化，产生具有专属 1,2-反式非对映控制的硫二糖。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany , 2008)
• Thiodisaccharides with galactofuranose or arabinofuranose as terminal units: Synthesis and inhibitory activity of an exo β-d-galactofuranosidase
  作者：Evangelina Repetto、Carla Marino、M. Laura Uhrig、Oscar Varela

  DOI：10.1016/j.bmc.2009.02.045

  日期：2009.4

  Thiodisaccharides having beta-D-Galf or alpha-L-Araf units as non-reducing end have been synthesized by the SnCl4- or MoO2Cl2-promoted thioglycosylation of per-O-benzoyl-D-galactofuranose (1), its 1-O-acetyl analogue 4, or per-O-acetyl-alpha-L-arabinofuranose (16) with 6-thioglucose or 6-thiogalactose derivatives. After convenient removal of the protecting groups, the free thiodisaccharides having the basic structure beta-D-Galf(1 -> 6)-6-thio-alpha-D-Glcp-OMe (5) or beta-D-Galf(1 -> 6)-6-thio-alpha-D-Galp-OMe (15) were obtained. The respective alpha-L-Araf analogues 18 and 20 were prepared similarly from 16. Alternatively, beta-D-Galf(1 -> 4)-4-thio- 3-deoxy-alpha-L-Xylp-OiPr was synthesized by Michael addition to a sugar enone of 1-thio-beta-D-Galf derivative, generated in situ from the glycosyl isothiourea derivative of 1. The free S-linked disaccharides were evaluated as inhibitors of the beta-galactofuranosidase from Penicillium fellutanum, being 15 and 20 the more active inhibitors against this enzyme. (c) 2009 Elsevier Ltd. All rights reserved.
• Rhenium(V)-Catalyzed Synthesis of 2-Deoxy-α-glycosides
  作者：Benjamin D. Sherry、Rebecca N. Loy、F. Dean Toste

  DOI：10.1021/ja031895t

  日期：2004.4.1

  A mild method for the synthesis of 2-deoxysugars from the coupling of glycals with a range of nucleophiles is described. The method employs 1 mol % of an air- and moisture-tolerant rhenium-oxo complex [ReOCl3(SMe2)(Ph3PO)] as a catalyst for the formation of O-, N-, and S-alpha-glycosides. The catalytic system tolerates a number of commonly employed protecting groups, including isopropylidene acetals, alkyl and silyl ethers, acetates, and benzoates. Furthermore, the high-oxidation-state complex selectively catalyzes the coupling with the glycal acceptor in preference to oxidation of the glycals, alcohols, and even thiols.
• Copper-Catalyzed C2- or C3-Thioglycosylation of Indoles with <i>N</i>-(Thioglycosides)succinimides: An Effective Strategy for the Total Synthesis of Isatindigotindolosides
  作者：Jie Huang、Wen-Wu Sun、Jin-Quan Li、Ao-Di Ma、Ji-Kai Liu、Bin Wu

  DOI：10.1021/acs.orglett.2c04270

  日期：2023.1.27

  alkaloid glucosides. This reaction is widely tolerant of functional groups, as various indoles and thioglycosides are suitable. It also provides a reliable method for performing late-stage modifications of natural products, such as gramine and melatonin. Total syntheses of isatindigotindolosides I and II were successfully accomplished using the C2-thioglycosylation reaction as a key step.

  Isatindigotindolosides 是一种在 C2 位含有 1 - S -β-吡喃葡萄糖基单元的吲哚，具有良好的生物活性。在这里，我们报告了铜催化的吲哚 C2- 或 C3- 硫糖基化与N -(硫代糖苷) 琥珀酰亚胺构建吲哚生物碱糖苷。该反应对官能团具有广泛的耐受性，因为各种吲哚和硫糖苷都是合适的。它还提供了一种可靠的方法来对天然产物（例如禾本科和褪黑激素）进行后期修饰。以 C2-硫糖基化反应为关键步骤，成功完成了靛蓝靛蓝苷I和II的全合成。