ethyl 2-O-acetyl-3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside | 383190-11-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-O-acetyl-3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside
• 英文别名: [(2S,3R,4R,5S,6S)-2-ethylsulfanyl-6-methyl-4,5-bis(phenylmethoxy)oxan-3-yl] acetate
• CAS: 383190-11-2
• 化学式: C₂₄H₃₀O₅S
• 分子量: 430.565
• InChiKey: XCTBVKFEKBZTAN-RUWBUGSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  79.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 2-O-acetyl-3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside 在 甲醇 、 N-碘代丁二酰亚胺 、 perchloric acid supported over silica 、 sodium methylate 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 p-methoxyphenyl (3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1→2)-(3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1→2)-3,4-di-O-benzyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  大肠杆菌19ab细胞壁O抗原五糖重复单元的简便合成。

  摘要：

  使用单糖中间体的连续糖基化，已经以优异的产率实现了具有与大肠杆菌19ab的细胞壁O-抗原相对应的所有α-连接的糖基键的五糖的直接合成。目标化合物及其合成中间体的结构通过光谱分析得到明确表征。在所有糖基化中都使用了通用的糖基化条件，并且在目标化合物的合成过程中涉及最少数量的保护基操纵。

  DOI：

  10.1016/j.carres.2012.09.005
• 作为产物：
  描述：

  苯甲醛二甲缩醛 在 吡啶 、 lithium aluminium tetrahydride 、 三氯化铝 、 sodium hydride 、 对甲苯磺酸 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.25h， 生成 ethyl 2-O-acetyl-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

• Synthesis of the tetrasaccharide repeating unit of the O-antigen of the Escherichia coli O69 strain and its conformational analysis
  作者：Manas Jana、Rajiv Kumar Kar、Anirban Bhunia、Anup Kumar Misra

  DOI：10.1039/c4ra06989g

  日期：——

  A straightforward synthesis of the tetrasaccharide repeating unit of the O-antigen of the Escherichia coli O69 strain as its 2-aminoethyl glycoside has been accomplished by carrying out two iterative glycosylations in one pot. The stereochemical outcome of the glycosylations was very good. The conformational analysis of the synthesized tetrasaccharide was carried out using NOE based two-dimensional

  大肠杆菌O69菌株O抗原的四糖重复单元作为其2-氨基乙基糖苷的直接合成已通过在一个罐中进行两次迭代糖基化来完成。糖基化的立体化学结果非常好。合成的四糖的构象分析是使用基于NOE的二维ROESY光谱技术结合所有原子的明确分子动力学模拟研究进行的。发现溶剂扰动引起的四糖1的构象在溶液中相当稳定。
• La(OTf)3: An Efficient Promoter for Thioglycoside Activation in Conjunction with N-Iodosuccinimide
  作者：Balaram Mukhopadhyay、Somnath Mukherjee

  DOI：10.1055/s-0030-1259016

  日期：2010.12

  Use of La(OTf)3 as a Lewis acid promoter for N-iodosuccinimide-mediated activation of thioglycosides is reported. The glycosylation reactions proceeded smoothly with good to excellent yields and stereoselectivity.

  使用La(OTf)3作为路易斯酸促使剂，报告了N-碘代琥珀酰亚胺介导的硫糖苷活化。糖苷化反应顺利进行，产率良好至优异，立体选择性也很好。
• 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 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。
• Synthesis of the Heptasaccharide Repeating Unit of the Cell Wall O-Polysaccharide of Enterotoxigenic<i>Escherichia coli</i>O139
  作者：Tamashree Ghosh、Anup Kumar Misra

  DOI：10.1002/open.201500164

  日期：2016.2

  convenient synthetic strategy was developed for the synthesis of the heptasaccharide repeating unit of the cell wall lipopolysaccharide of the E. coli O139 strain. The p‐methoxybenzyl (PMB) group was used as a temporary protecting group which was removed in situ under the glycosylation conditions by changing the reaction temperature during the synthesis of the target compound. All glycosylation steps gave

  产肠毒素大肠杆菌(ETEC)，如 O139 菌株，主要导致旅行者腹泻，并引起猪、牛和家禽疾病。开发了一种方便的合成策略来合成大肠杆菌O139菌株细胞壁脂多糖的七糖重复单元。对甲氧基苄基（PMB）基团用作临时保护基团，在目标化合物合成过程中通过改变反应温度在糖基化条件下原位去除。所有糖基化步骤均具有高产率和良好的立体选择性。在合成后期使用双相反应条件进行了（2,2,6,6-四甲基哌啶-1-基）氧基（TEMPO）介导的伯羟基选择性氧化。这种合成的寡糖随后可以与蛋白质有效地缀合，以制备作为候选疫苗的糖缀合物衍生物。