methyl 6-S-acetyl-2,3,4-tri-O-acetyl-α-D-glucopyranoside | 54497-98-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 6-S-acetyl-2,3,4-tri-O-acetyl-α-D-glucopyranoside
• 英文别名: methyl 2,3,4-tri-O-acetyl-6-acetylthio-α-D-glucopyranoside；[(2S,3S,4S,5R,6S)-4,5-diacetyloxy-2-(acetylsulfanylmethyl)-6-methoxyoxan-3-yl] acetate
• CAS: 54497-98-2
• 化学式: C₁₅H₂₂O₉S
• 分子量: 378.4
• InChiKey: KGPJKVYHVUTECA-QMIVOQANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl 6-S-acetyl-2,3,4-tri-O-acetyl-α-D-glucopyranoside 在 一水合肼 、 三(2-羰基乙基)磷盐酸盐 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.03h， 以87%的产率得到methyl 2,3,4-tri-O-acetyl-6-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  A One-Pot Method for Removal of Thioacetyl Group via Desulfurization under Ultraviolet Light To Synthesize Deoxyglycosides

  摘要：

  We herein developed an efficient method for removing thioacetyl to synthesize acylated deoxy glycosides in a one-pot reaction, where the thioacetyl was selectively deacetylated by hydrazine hydrate in DMF within 2-5 min at room temperature, followed by desulfurization under UV light for 1-2 h in the presence of TCEP center dot HCl. The method was then used to synthesize 2-deoxy glycosides with absolute alpha/beta-configuration via stereoselective control of C-2 thioacetate in glycosylation.

  DOI：

  10.1021/acs.orglett.9b02033
• 作为产物：
  描述：

  methyl 6-O-tosyl-α-D-glucopyranoside 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 methyl 6-S-acetyl-2,3,4-tri-O-acetyl-α-D-glucopyranoside
  参考文献：
  名称：

  基于磺基奎诺糖支架的磷脂酰肌醇 3-磷酸盐模拟物：作为蛋白激酶 B 抑制剂的合成和评价

  摘要：

  基于磺基奎诺糖支架合成了新的 3-磷酸磷脂酰肌醇磺基奎诺糖类似物，作为潜在的蛋白激酶 B (PKB) 抑制剂。合成策略包括将 6 位硫代乙酸酯基团和异头位置的叠氮基团引入葡萄糖，作为最终化合物中存在的磺酸盐和氨基磷酸酯部分的前体。合成的化合物通过 ELISA 测定在体外对分离的 PKB 进行了测试，并测试了它们对人卵巢癌细胞系 IGROV-1 的抗增殖活性。磺基喹诺酮衍生物 2b 和 2c 在低微摩尔范围内显示出抑制活性。

  DOI：

  10.1002/ejoc.201402664

文献信息

• Synthesis and In Vitro Biological Properties of Novel Cationic Derivatives of Amphotericin B
  作者：Valérie Paquet、Astrid A. Volmer、Erick M. Carreira

  DOI：10.1002/chem.200701237

  日期：2008.3.7

  Novel cationic amphotericin B derivatives as highly potent antifungal agents are reported. These semi-synthetic derivatives of amphotericin B were elaborated through a series of modifications both on the nitrogen atom of the mycosamine and on the C-16 carboxylic acid moiety. The antifungal activity of the new conjugates was tested against Saccharomyces cerevisiae and also against nine different strains

  据报道新型阳离子两性霉素B衍生物作为高效抗真菌剂。两性霉素B的这些半合成衍生物是通过在霉菌胺的氮原子和C-16羧酸部分上进行一系列修饰而制成的。测试了新缀合物的抗真菌活性对啤酒酵母以及对白色念珠菌和光滑念珠菌的九种不同菌株，包括两性霉素抗性菌株。在多胺衍生物在霉菌胺上带有两个3-氨基丙基链的情况下，观察到了高效力。生物学性质的评估还包括通过测量EH50值确定化合物的溶血活性。
• Comprehensive Synthesis of Substrates, Intermediates, and Products of the Sulfoglycolytic Embden–Meyerhoff–Parnas Pathway
  作者：Palika Abayakoon、Ruwan Epa、Marija Petricevic、Christopher Bengt、Janice W.-Y. Mui、Phillip L. van der Peet、Yunyang Zhang、James P. Lingford、Jonathan M. White、Ethan D. Goddard-Borger、Spencer J. Williams

  DOI：10.1021/acs.joc.9b00055

  日期：2019.3.1

  Delineating the molecular details of sulfoglycolysis requires authentic samples of the various metabolites in these pathways. To this end, we have established chemical and chemoenzymatic methods for the synthesis of the key organosulfur metabolites sulfoquinovosylglycerol, SQ (also in 13C6-labeled form), sulfofructose, sulfofructose-1-phosphate, sulfolactaldehyde, and 2,3-dihydroxypropanesulfonate, as well

  磺基糖酵解是一种代谢途径，专门用于将磺基糖磺基古诺糖（SQ）分解为较小的有机硫片段。每年估计有100亿吨SQ通量通过糖基糖酵解途径，这使其成为生物地球化学硫循环的重要方面。描述磺基糖酵解的分子细节需要这些途径中各种代谢物的真实样品。为此，我们已经建立了化学和化学酶促方法，用于合成关键的有机硫代谢物磺基喹硫基甘油SQ（也在13 C 6中-标记的形式），亚铁果糖，亚果糖-1-磷酸盐，巯基乙醛和2,3-二羟基丙烷磺酸盐，以及通往发色磺基喹硫糖苷酶底物4-硝基苯基α-磺基奎奴糖苷的改进途径。
• The Synthesis of Various 1,6-Disulfide-Bridged D-Hexopyranoses
  作者：Ethan D. Goddard-Borger、Robert V. Stick

  DOI：10.1071/ch04277

  日期：——

  1,6-Disulfide-bridged derivatives have been prepared for d-gluco-, d-manno-, d-allo-, d-galacto-, and d-talo-pyranose, in the main by the nucleophilic attack of a C6 thiolate onto an anomeric thiosulfonate. The d-gluco disulfide, ‘angyalosan’, was successfully oxidized to a single thiosulfinate.

  1,6 二甲基二硫键衍生物的制备主要是通过 C6 硫代硫酸酯与异构体硫代磺酸酯的亲核反应，制备出了 d-葡糖、d-甘露糖、d-异甘露糖、d-半乳糖和 d-塔罗吡喃糖。d- 葡萄糖二硫化物 "anggyalosan "被成功氧化成单一的硫代亚硫酸盐。
• Direct Stereoselective Synthesis of β-Thiomannosides
  作者：David Crich、Hongmei Li

  DOI：10.1021/jo9914667

  日期：2000.2.1

  A highly diastereoselective synthesis of beta-thiomannopyranosides is described in which S-phenyl 2,3-di-0-benzyl-4,6-O-benzylidene-1-deoxy-1-thia-alpha-D-mannopyranoside S-oxide is treated with triflic anhydride and 2,6-di-tert-butyl-4-methylpyridine in CH2Cl2 at -78 degrees C leading to the formation of an intermediate alpha-mannosyl triflate. Addition of primary, secondary, or tertiary thiols then leads to the beta-thiomannosides, by an S(N)2-like displacement, in good yield and with excellent stereoselectivity. Deprotection is achieved either by Birch reduction or by Zemplen deacetylation, of the acetyl protected aglycons, followed by hydrogenolysis over Pearlman's catalyst. The assignment of configuration of the beta-thiomannopyranosides is discussed in terms of the chemical shift of the mannose H5 resonance and the (1)J(CH) of the mannose anomeric carbon.
• Synthesis of S-linked carbohydrate analogues via a Ferrier reaction
  作者：David Ellis、Sarah E. Norman、Helen M.I. Osborn

  DOI：10.1016/j.tet.2008.01.042

  日期：2008.3

  In this work, the synthetic utility of the Ferrier reaction to access S-linked disaccharides and S-linked glycoamino acids has been probed. Significantly, entry to a range of 1,4- and 1,6-S-linked disaccharides has been achieved using glycals derived from glucose and galactose, and sulfur containing coupling partners derived from methyl alpha-D-glucopyranoside. Access to S-linked glycoamino acids and glycopeptides has also been achieved using protected cysteine and homocysteine coupling partners within the Ferrier reaction. Functionalisation of the Ferrier products, for example, via dihydroxylation using OsO4 or amino acid coupling, and deprotection of the targets have also been achieved. In this way, entry to materials of interest as mimics of biologically interesting disaccharides and glycopeptides has been realised, including targets derived from rare sugars such as talopyranose and gulopyranose. (C) 2008 Elsevier Ltd. All rights reserved.