ethyl-[O²,O³,O⁶-triacetyl-O⁴-(tetra-O-acetyl-β-D-glucopyranosyl)-1-thio-β-D-glucopyranoside] | 210223-72-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl-[O²,O³,O⁶-triacetyl-O⁴-(tetra-O-acetyl-β-D-glucopyranosyl)-1-thio-β-D-glucopyranoside]
• 英文别名: Aethyl-[O²,O³,O⁶-triacetyl-O⁴-(tetra-O-acetyl-β-D-glucopyranosyl)-1-thio-β-D-glucopyranosid]；Glc2Ac3Ac4Ac6Ac(b1-4)Glc2Ac3Ac6Ac(b)-SEt；[(2R,3R,4S,5R,6S)-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: 210223-72-6
• 化学式: C₂₈H₄₀O₁₇S
• 分子量: 680.681
• InChiKey: WUANIQLTJBQGJW-AXXYRMHMSA-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-[O²,O³,O⁶-triacetyl-O⁴-(tetra-O-acetyl-β-D-glucopyranosyl)-1-thio-β-D-glucopyranoside] 在 (1S)-(+)-10-camphorsulfonic acid 、 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0~55.0 ℃ 、3.0 kPa 条件下， 反应 18.5h， 生成
  参考文献：
  名称：

  与肺炎链球菌3型荚膜多糖片段结构相关的寡糖的合成

  摘要：

  摘要 合成了与肺炎链球菌 3 型荚膜多糖片段结构相关的二糖、三糖和四糖的 3-氨基丙基糖苷。

  DOI：

  10.1007/s11172-017-1708-9
• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl isothiourea 、 alkaline earth salt of/the/ methylsulfuric acid 在 三乙胺 作用下， 以 乙腈 为溶剂， 生成 ethyl-[O²,O³,O⁶-triacetyl-O⁴-(tetra-O-acetyl-β-D-glucopyranosyl)-1-thio-β-D-glucopyranoside]
  参考文献：
  名称：

  Reaction of 1,2-trans-glycosyl acetates with thiourea: a new entry to 1-thiosugars

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2003.08.120

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。
• 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.
• Wrede; Hettche, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1927, vol. 172, p. 169,173
  作者：Wrede、Hettche

  DOI：——

  日期：——
• 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.