ethyl 3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside | 130847-19-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside
• 英文别名: ethyl 3,4-di-O-benzyl-1-thio-alpha-l-rhamnopyranoside；(2S,3R,4S,5S,6S)-2-ethylsulfanyl-6-methyl-4,5-bis(phenylmethoxy)oxan-3-ol
• CAS: 130847-19-7
• 化学式: C₂₂H₂₈O₄S
• 分子量: 388.528
• InChiKey: GFUOWSUGSKLNRX-ODQRPKBASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  73.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside 在 2,4,6-三甲基吡啶 、 4 A molecular sieve 、 溴 、 sodium methylate 、 silver trifluoromethanesulfonate 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 0.5h， 生成 2,3,4,6-Tetra-O-benzyl-β-D-Glcp-(1->2)-3,4-di-O-benzyl-β-L-Rhap-OMe
  参考文献：
  名称：

  Jansson, Per-Erik; Kenne, Lennart; Ottoson, Hakan, Journal of the Chemical Society. Perkin transactions I, 1990, # 7, p. 2011 - 2018

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl 2,3-O-benzylidene-1-thio-α-L-rhamnopyranoside 在 lithium aluminium tetrahydride 、 三氯化铝 、 sodium hydride 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 ethyl 3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis of the α-d-GlcpA-(1→3)-α-l-Rhap-(1→2)-l-Rha trisaccharide isolated from the cell wall hydrolyzate of the green alga, Chlorella vulgaris

  摘要：

  The title trisaccharide was synthesized from 6-O-acetyl-2,3,4-tri-O-benzyl-alpha -D-glucopyranosyl chloride (10), ethyl 2,4-di-O-benzyl-1-thio- (5) and benzyl 3,4-di-O-benzyl-alpha -L-rhamnopyranoside (9). The disaccharide 11 obtained from compounds 5 and 10 was used as the glycosyl donor to glycosylate the rhamnopyranoside derivative 9 having free OH-2 using the NIS-AgOTf-mediated glycosylation methodology. Zemplen deacetylation of the trisaccharide 12 resulted in the 6 " -OH derivative (13), which was selectively oxidized with CrO3 to the uronic acid derivative 14. The benzyl groups were removed by catalytic hydrogenolysis to furnish the target trisaccharide (1). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00196-3

文献信息

• Convergent Synthesis and Conformational Analysis of the Hexasaccharide Repeating Unit of the<i>O</i>-Antigen of<i>Shigella flexneri</i>Serotype 1d
  作者：Debashis Dhara、Rajiv Kumar Kar、Anirban Bhunia、Anup Kumar Misra

  DOI：10.1002/ejoc.201402392

  日期：2014.7

  A hexasaccharide repeating unit of the O-antigen of the cell wall of Shigella flexneri type 1d has been synthesized using a stereoselective [3+3] block glycosylation approach. Recently developed glycosylation conditions were used in the synthesis. A thioglycoside was used as an orthogonal glycosyl donor during the synthesis. The synthesized hexasaccharide was subjected to detailed NMR spectroscopic

  已使用立体选择性 [3+3] 阻断糖基化方法合成了 1d 型志贺氏菌细胞壁 O-抗原的六糖重复单元。最近开发的糖基化条件用于合成。在合成过程中使用硫糖苷作为正交糖基供体。合成的六糖经过详细的核磁共振光谱和分子建模研究，以确定其在水中的构象行为。基于 NOE 的二维 NOSY 实验和全原子显式分子动力学 (MD) 模拟研究表明，低聚糖不是很灵活，它在糖部分之间的糖苷键方面保持刚性。
• Facile synthesis of a pentasaccharide repeating unit corresponding to the common O-antigen of Salmonella enterica O57 and Escherichia coli O51
  作者：Tamashree Ghosh、Abhishek Santra、Anup Kumar Misra

  DOI：10.1016/j.tetasy.2013.04.001

  日期：2013.5

  for the synthesis of a pentasaccharide present in the O-antigen of Salmonella enterica O57 and Escherichia coli O51 strains. A sequential glycosylation strategy has been adopted for the synthesis of the target pentasaccharide. All intermediate steps are high yielding and the glycosylation steps are stereoselective. A number of recently developed methodologies have been used in the synthesis.

  已经开发出一种简明的化学合成策略来合成存在于肠沙门氏菌O57和大肠杆菌O51菌株的O-抗原中的五糖。已采用顺序糖基化策略来合成目标五糖。所有中间步骤都是高产率的，糖基化步骤是立体选择性的。综合中已使用了许多最新开发的方法。
• Synthesis of a Trisaccharide and a Tetrasaccharide from the Cell-Wall Lipopolysaccharides of Azospirillum brasilense S17
  作者：Anup Misra、Shashi Pandey、Samir Ghosh

  DOI：10.1055/s-0029-1217401

  日期：2009.8

  A trisaccharide containing a d-mannosamine moiety and a tetrasaccharide containing an l-rhamnan chain that are found in the cell walls of Azospirillum brasilense S17 were synthesized concisely and in excellent yields. The key features of the synthetic strategy were stereoselective glycosylations and a minimum number of protecting-group manipulations. oligosaccharides - glycosylations - d-mannosamine

  简明地并且以优异的产率合成了在d.Asilspirillum brasilense S17的细胞壁中发现的包含d-甘露糖胺部分的三糖和包含1 - rhamnan链的四糖。合成策略的关键特征是立体选择性糖基化和最少数量的保护基操纵。 低聚糖-糖基化- d -mannosamine -巴西固氮螺菌-根瘤菌
• Synthesis of a hexasaccharide repeating unit of the cell wall polysaccharide of Bifidobacterium animalis subsp. lactis LKM512
  作者：Pradip Shit、Anup Kumar Misra

  DOI：10.1016/j.carres.2018.12.014

  日期：2019.2

  A convergent synthesis of the hexasaccharide as its 2-aminoethyl glycoside corresponding to the repeating unit of the cell wall polysaccharide of Bifidobacterium animalis subsp. lactis LKM512 has been achieved applying a [4 + 2] glycosylation strategy. The disaccharide thioglycoside donor was prepared by combining a d-galactofuranosyl thioglycoside with another l-rhamnosyl thioglycoside acceptor. The

  收敛合成六糖作为其2-氨基乙基糖苷，对应于动物双歧杆菌亚种细胞壁多糖的重复单元。采用[4 + 2]糖基化策略可实现乳酸LKM512。通过将d-半乳糖呋喃糖基硫糖苷与另一种1-鼠李糖基硫糖苷受体结合来制备二糖硫糖苷供体。各个糖基化步骤的产率非常令人满意，并且立体效果优异。六糖中的d-半乳糖呋喃糖基部分的α-糖苷键以非常高的产率获得。
• Straightforward synthesis of the hexasaccharide repeating unit of the O-specific polysaccharide of Salmonella arizonae O62
  作者：Abhijit Rana、Pradip Shit、Anup Kumar Misra

  DOI：10.1007/s10719-023-10122-x

  日期：2023.8

  A straightforward synthesis of the hexasaccharide repeating unit of the O-specific polysaccharide of Salmonella arizonae O62 was achieved in very good yield applying sequential glycosylation strategy. Successful regioselective glycosylation of the di-hydroxylated L-rhamnose moiety allowed achieving the desired compound in minimum number of synthetic steps. TEMPO catalyzed and [bis(acetoxy)iodo]benzene

  应用顺序糖基化策略，以非常好的收率实现了亚利桑那沙门氏菌 O62的O特异性多糖的六糖重复单元的直接合成。二羟基化 L-鼠李糖部分的成功区域选择性糖基化允许以最少的合成步骤获得所需的化合物。在六糖衍生物中，TEMPO 催化和[双(乙酰氧基)碘]苯(BAIB) 介导的伯羟基在后期区域选择性氧化成羧酸。糖基化步骤产率高，立体化学结果高。从适当功能化的单糖中间体开始，经过十四个步骤，获得了所需的六糖，总产率为 7%。