ethyl 2,3,6,2',3',4',6'-hepta-O-acetyl-1-thio-β-D-maltoside | 33600-53-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2,3,6,2',3',4',6'-hepta-O-acetyl-1-thio-β-D-maltoside
• 英文别名: Glc2Ac3Ac4Ac6Ac(a1-4)Glc2Ac3Ac6Ac(b)-SEt；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(2R,3R,4S,5R,6S)-4,5-diacetyloxy-2-(acetyloxymethyl)-6-ethylsulfanyloxan-3-yl]oxyoxan-2-yl]methyl acetate
• CAS: 33600-53-2
• 化学式: C₂₈H₄₀O₁₇S
• 分子量: 680.681
• InChiKey: WUANIQLTJBQGJW-HYSGBLIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  46
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  237
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  ethyl 2,3,6,2',3',4',6'-hepta-O-acetyl-1-thio-β-D-maltoside 在 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 Ethyl O-(4,6-O-benzylidene-α-D-glucopyranosyl)-(1->4)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Westman, Jacob; Nilsson, Marianne, Journal of Carbohydrate Chemistry, 1995, vol. 14, # 7, p. 949 - 960

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2,3,6,2',3',4',6'-octa-O-acetylmaltose 以81%的产率得到ethyl 2,3,6,2',3',4',6'-hepta-O-acetyl-1-thio-β-D-maltoside
  参考文献：
  名称：

  芳基糖基砜合成一些 1,6-脱水二糖

  摘要：

  1,6-脱水-乳糖、-麦芽糖和-纤维二糖实际上是在温和的反应条件下制备的，并且通过来自相应二糖的各种芳基糖基砜的碱性降解以相当好的收率制备。

  DOI：

  10.1246/cl.1987.2065

文献信息

• Glycosylation and Pyranose-Furanose Isomerization of Carbohydrates Using HClO₄-SiO₂: Synthesis of Oligosaccharides Containing Galactofuranose
  作者：Anup Misra、Chinmoy Mukherjee

  DOI：10.1055/s-2007-965913

  日期：2007.3

  A series of di- and trisaccharides containing 6-O-linked galactofuranose were synthesized as an anomeric mixture of methyl glycosides using silica-supported perchloric acid.

  一系列含有6-O-连接的呋喃半乳糖的二糖和三糖被合成，它们是以甲基糖苷的异头混合物形式，通过硅胶负载的高氯酸作为催化剂。
• Glycosylation Enabled by Successive Rhodium(II) and Brønsted Acid Catalysis
  作者：Lingkui Meng、Peng Wu、Jing Fang、Ying Xiao、Xiong Xiao、Guangsheng Tu、Xiang Ma、Shuang Teng、Jing Zeng、Qian Wan

  DOI：10.1021/jacs.9b04619

  日期：2019.7.31

  reaction comprises two chronological meticulously-designed catalytic cycles: 1) rhodium-catalyzed formation of sulfonium ylide; 2) Brønsted acid-catalyzed formation of sulfonium ion. This protocol highlight-ed an effective and robust tactic to prepare glycosyl sulfonium ion from glycosyl sulfonium ylide precursor amenable for glycosylation.

  在此，我们报道了一种高效的糖基化反应，包括两个按时间顺序精心设计的催化循环：1）铑催化形成锍叶立德；2) Brønsted 酸催化形成锍离子。该协议强调了一种有效且稳健的策略，可从适合糖基化的糖基锍叶立德前体制备糖基锍离子。
• Reaction of 1,2-trans-glycosyl acetates with thiourea: a new entry to 1-thiosugars
  作者：Farid M. Ibatullin、Konstantin A. Shabalin、Janne V. Jänis、Alexander G. Shavva

  DOI：10.1016/j.tetlet.2003.08.120

  日期：2003.10

  The reaction of 1,2-trans-glycosyl acetates with thiourea Under boron trifluoride etherate catalysis affording acetylated S-glycosyl isothiourea derivatives is described. The isothiourea derivatives obtained can be readily transformed into the desired 1-thiosugar derivative by reaction with triethylamine and Subsequent alkylation or acylation of the in situ formed 1-thioaldose. (C) 2003 Elsevier Ltd. All rights reserved.
• Unprecedented Transformation of Thioglycosides to Their Corresponding 1‐<i>O</i>‐Acetates in the Presence of HClO₄‐SiO₂§
  作者：Geetanjali Agnihotri、Pallavi Tiwari、Anup Kumar Misra

  DOI：10.1080/07328300600860153

  日期：2006.8

  An unprecedented conversion of thioalkyl/aryl glycoside to the corresponding 1-O-acetates has been described using acetic anhydride and HClO4-SiO2 at rt. Although this transformation does not play an important role in the oligosaccharide synthesis in comparison to its reverse transformation, this gives useful information in selecting the reaction condition for the synthesis of oligosaccharides. The yields were excellent in all cases.
• Trisaccharide synthesis by glycosyl transfer from p-nitrophenyl β-d-N-acetylgalactosaminide on to disaccharide acceptors catalysed by the β-N-acetylhexosaminidase from Aspergillus oryzae
  作者：Suddham Singh、Michaela Scigelova、Peter Critchley、David H.G. Crout

  DOI：10.1016/s0008-6215(97)10030-1

  日期：1997.12

  The beta-N-acetylhexosaminidase from Aspergillus oryzae catalysed the transfer of beta-D-N-acetylgalactosaminyl residues from p-nitrophenyl beta-D-N-acetylglucosaminide on to disaccharide accepters consisting of thioethyl glycosides of alpha-D-Glc-(1 --> 4)-beta-D-Glc, beta-D-Glc-(1 --> 4)-beta-D-Glc and beta-D-Glc-(1 --> 6)-beta-D-Glc. The principle of 'anomeric control' was exemplified by the results which showed that an alpha-linkage between the units of the acceptor favoured exclusively the formation of a new (1 --> 4)-linkage, whereas the beta-configuration in the acceptor led to a mixture of (1 --> 4)- and (1 --> 3)-linked products, as observed for simple glycosides of monosaccharide accepters. With the thioethyl beta-lactoside as acceptor, beta-D-Gal(1 --> 6)-beta-D-Gal-(1 --> 4)-beta-D-GlcSEt was formed, owing to the action of residual beta-D-galactosidase activity in the N-acetylhexosaminidase on the thioethyl beta-lactoside acting as both donor and acceptor. (C) 1998 Elsevier Science Ltd.