Ethyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside | 128643-88-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Ethyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-6-ethylsulfanyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]methyl acetate
• CAS: 128643-88-9
• 化学式: C₃₁H₃₆O₆S
• 分子量: 536.689
• InChiKey: MOKWTSWGDQYBLT-SAEUYMBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  38
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  88.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Ethyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside 在 ammonium heptamolybdate 、 高氯酸 、 双氧水 、 溴化铵 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.25h， 以70%的产率得到6-O-acetyl-2,3,4-tri-O-benzyl-D-glucopyranose
  参考文献：
  名称：

  一种有用且方便的硫糖苷水解合成方法

  摘要：

  通过使用 (NH4)6Mo7O24·4H2O-H2O2 或 H2MoO4·H2O-H2O2 促进溴化铵在CH2Cl2-H2O 溶剂体系中的高氯酸。温和的条件、良好的收率、在异头位置或双键处无副反应（如溴化），甚至在硫处氧化是一些主要优点。

  DOI：

  10.1246/cl.2002.210
• 作为产物：
  描述：

  ethyl 2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside 、 乙酸酐 以 吡啶 为溶剂， 以97%的产率得到Ethyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  克雷伯菌23型多糖的四糖重复单元的合成

  摘要：

  通过缩合甲基2，获得2-O-烯丙基-4-O-苄基-3-O-（2,3,4,6-四-O-乙酰基-β-D-吡喃吡喃糖基）-α-L-鼠李糖吡喃糖苷-O-烯丙基-4-O-苄基-α-L-鼠李吡喃糖苷与四-O-乙酰基-α-D-吡喃葡萄糖基溴化物。苯甲酰化，除去烯丙基，并将产物与乙基6-O-乙酰基-2,3,4-三-O-苄基-1-硫代-β-D-吡喃葡萄糖苷缩合，得到甲基2-O-（6 -O-乙酰基-2,3,4-三-O-苄基-α-D-吡喃葡萄糖基）-4-O-苄基-3-O-（2,3,4,6-四-O-苄基-β -D-吡喃葡萄糖基）-α-L-鼠李糖吡喃糖苷。O-脱乙酰基，产物与（2,3,4-三-O-乙酰基-α-D-吡喃葡萄糖基溴）甲基缩合，并除去保护基，得到3-O-β-D-吡喃葡萄糖基甲基-2-O- [6-O-（β-D-吡喃葡萄糖基糖醛酸）-α-D-吡喃葡萄糖基]-α-L-鼠李糖苷（13）。

  DOI：

  10.1016/0008-6215(90)84108-7

文献信息

• Acetonyltriphenylphosphonium Bromide (ATPB): A Versatile Reagent for the Acylation of Alcohols, Phenols, Thiols and Amines and for 1,1-Diacylation of Aldehydes under Solvent-Free Conditions
  作者：Abu T. Khan、Lokman H. Choudhury、Subrata Ghosh

  DOI：10.1002/ejoc.200500066

  日期：2005.7

  A wide variety of alcohols, phenols, amines and thiols may easily be converted into the corresponding acetate derivatives by treatment with acetic anhydride (1.5–2.0 equivalents) in the presence of acetonyltriphenylphosphonium bromide (ATPB; 5 mol %) in good yields at room temperature. With the same precatalyst, both aliphatic and aromatic aldehydes can also be transformed into the corresponding gem-diacetates

  在室温下，在丙酮基三苯基溴化鏻（ATPB；5 mol%）存在下，通过用乙酸酐（1.5-2.0 当量）处理，可以很容易地将多种醇、酚、胺和硫醇转化为相应的乙酸衍生物. 使用相同的预催化剂，脂肪醛和芳香醛也可以在回流条件下转化为相应的双乙酸酯。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• Synthesis of potassium (2R)-2-O-α-d-glucopyranosyl-(1→6)-α-d-glucopyranosyl-2,3-dihydroxypropanoate a natural compatible solute
  作者：Eva C. Lourenço、Christopher D. Maycock、M. Rita Ventura

  DOI：10.1016/j.carres.2009.06.037

  日期：2009.10

  4-tribenzyl-1-thio-d-glucopyranoside, as a mixture of anomers, was employed for the stereoselective synthesis of the potassium salt of (2R)-2-O-alpha-d-glucopyranosyl-(1-->6)-alpha-d-glucopyranosyl-2,3-dihydroxypropa noic acid (alpha-d-glucosyl-(1-->6)-alpha-d-glucosyl-(1-->2)-d-glyceric acid, GGG), a recently isolated compatible solute. The alpha-anomer was by far the major product of both glycosylation reactions using

  作为异构体的混合物，将乙基6-O-乙酰基-2,3,4-三苄基-1-硫代-d-吡喃葡萄糖苷用于（2R）-2-O-α-钾盐的立体选择性合成d-吡喃葡萄糖基-（1-> 6）-α-d-吡喃葡萄糖基-2,3-二羟基丙酸（α-d-葡萄糖基-（1-> 6）-alpha-d-葡萄糖基-（1-- > 2）-d-甘油酸（GGG），最近分离出的相容溶质。到目前为止，使用NIS / TfOH作为活化剂，α-端基异构体是两个糖基化反应的主要产物。
• Synthesis of the tetrasaccharide repeating unit of the antigen from Klebsiella type 2
  作者：Anup Kumar Misra、Nirmolendu Roy

  DOI：10.1016/0008-6215(95)00231-x

  日期：1995.11

  been synthesized and condensed in the presence of methyl triflate to afford a tetrasaccharide derivative. Removal of protecting groups gave methyl 3-O-(methyl alpha-D-glucopyranosyluronate)-4-O-(3-O-alpha-D- glucopyranosyl-beta-D-glucopyranosyl)-beta-D-mannopyranoside (23), the repeating unit of the antigen from Klebsiella type 2, in the form of its methyl ester methyl glycoside.

  二糖乙基2,4,6-三-O-乙酰基-3-O-（2,3,4,6-四-O-苄基-α-D-吡喃葡萄糖基）-1-硫代-β-D-吡喃葡萄糖苷（6）和2,6-二-O-苄基-3-O-（2,3,4-三-O-苄基甲基-α-D-吡喃葡萄糖基尿酸甲酯）-β-D-甘露吡喃糖苷（21）在三氟甲磺酸甲酯的存在下进行合成和缩合，得到四糖衍生物。除去保护基，得到3-O-（甲基α-D-吡喃葡萄糖基尿酸）-4-O-（3-O-α-D-吡喃葡萄糖基-β-D-吡喃葡萄糖基）-β-D-甘露吡喃糖苷（23）， 2型克雷伯氏菌抗原的重复单元，以其甲酯甲基糖苷的形式存在。
• Straightforward synthesis of a tetrasaccharide repeating unit corresponding to the <i>O</i>-antigen of <i>Escherichia coli</i> O16
  作者：Manas Jana、Anup Kumar Misra

  DOI：10.3762/bjoc.9.203

  日期：——

  A straightforward synthesis of the tetrasaccharide repeating unit of the O-antigen of Escherichia coli O16 has been achieved following a sequential glycosylation strategy. A minimum number of steps was used for the synthesis of the target compound involving a one-pot glycosylation and a protecting group manipulation. All intermediate reactions afford their products in high yield, and the glycosylation steps are stereoselective.

  通过顺序糖基化策略，成功合成了大肠杆菌O16型O-抗原的四糖重复单元。在合成目标化合物时，使用了最少的步骤，包括一锅法糖基化和保护基操作。所有中间反应产物的收率都很高，糖基化步骤具有立体选择性。
• Convergent synthesis of a common pentasaccharide-repeating unit corresponding to the O-specific polysaccharide of Escherichia coli O4:K3, O4:K6, and O4:K12
  作者：Rajib Panchadhayee、Anup Kumar Misra

  DOI：10.1016/j.tetasy.2010.04.056

  日期：2010.4

  A convergent chemical synthesis of a pentasaccharide found in the O-specific polysaccharide of Escherichia coli O4.K3, O4:K6, and O4:K12 has been achieved in excellent yield. A [3+2] block synthetic strategy has been adopted to couple a disaccharide donor 11 with a trisaccharide acceptor 10 for the construction of the pentasaccharide derivative 12 which on deprotection furnished target pentasaccharide 1 as its 4-methoxyphenyl glycoside Disaccharide thioglycoside donor 11 and trisaccharide acceptor 10 were prepared from suitably protected monosaccharide intermediates Yields were excellent in all steps. (C) 2010 Elsevier Ltd All rights reserved.