p-tolyl 2-O-benzyl-1-thio-β-L-fucopyranoside | 1607433-63-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-tolyl 2-O-benzyl-1-thio-β-L-fucopyranoside
• 英文别名: (2S,3S,4R,5S,6R)-2-methyl-6-(4-methylphenyl)sulfanyl-5-phenylmethoxyoxane-3,4-diol
• CAS: 1607433-63-5
• 化学式: C₂₀H₂₄O₄S
• 分子量: 360.474
• InChiKey: YQYJIANXFLDKGD-JLTFKRJCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  84.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  p-tolyl 2-O-benzyl-1-thio-β-L-fucopyranoside 在 吡啶 、 四丁基碘化铵 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.17h， 生成 p-tolyl 2,3-di-O-benzyl-4-O-chloroacetyl-1-thio-β-L-fucopyranoside
  参考文献：
  名称：

  Chemical synthesis of a tetrasaccharide related to the exocellular polysaccharide from Rhodococcus sp. RHA1

  摘要：

  Chemical synthesis of the tetrasaccharide related to the exocellular polysaccharide from Rhodococcus sp. RHA1 is reported. The stereoselective glycosylations were achieved by activation of the thioglycoside donors using N-iodosuccinimide in the presence of La(OTf)(3) varying temperature per the need of 1,2-cis or 1,2-trans glycosylations. The target tetrasaccharide is reported in the form of its p-methoxyphenyl glycoside that can be cleaved selectively from the per-O-acetylated derivative allowing further glycoconjugate formation using trichloroacetimidate chemistry. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.05.018
• 作为产物：
  描述：

  6-deoxy-L-galactose 在 吡啶 、 4-二甲氨基吡啶 、 三氟化硼乙醚 、 sodium methylate 、 sodium hydride 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 71.5h， 生成 p-tolyl 2-O-benzyl-1-thio-β-L-fucopyranoside
  参考文献：
  名称：

  Stereoselective Synthesis of a Sulfated Tetrasaccharide Corresponding to a Rare Sequence in the Galactofucan Isolated from Sargassum polycystum

  摘要：

  The first chemical synthesis of a highly sulfated tetrasaccharide 1, as the rare sequence in the galactofucan isolated from the brown alga Sargassum polycystum, was achieved in a convergent and stereoselective manner. The key features of the synthetic strategy include construction of multiple contiguous 1,2-cis glycosidic bonds and [2 + 2] assembly based on the rationally developed D-galactose building block 6. The synthesized oligosaccharides were fully characterized using a combination of coupled-HSQC and other 2D NMR techniques.

  DOI：

  10.1021/jo500503r

文献信息

• One-Pot Regioselective Diacylation of Pyranoside 1,2-<i>cis</i> Diols
  作者：Taeok Kim、Michael R. Bell、V. Narasimharao Thota、Todd L. Lowary

  DOI：10.1021/acs.joc.2c00252

  日期：2022.4.1

  A one-pot strategy for functionalizing pyranoside 1,2-cis-diols with two different ester protecting groups is reported. The approach employs regioselective acylation via orthoester hydrolysis promoted by a carboxylic acid, e.g., levulinic acid, acetic acid, benzoic acid, or chloroacetic acid. Upon removal of water and introduction of a coupling agent, the carboxylic acid is esterified to the hydroxyl

  报道了一种用两种不同的酯保护基团对吡喃糖苷 1,2-顺式二醇进行功能化的一锅法。该方法通过由羧酸例如乙酰丙酸、乙酸、苯甲酸或氯乙酸促进的原酸酯水解使用区域选择性酰化。在除去水并引入偶联剂后，羧酸酯化为水解过程中释放的羟基。虽然适用于吡喃糖苷支架上的 1,2-顺式二醇，但该方法应适用于任何六元环上的此类基序。
• Synthesis of the acidic pentasaccharide repeating unit of the cell wall O-antigen of Providencia alcalifaciens O45:H25 strain
  作者：Abhijit Rana、Anup Kumar Misra

  DOI：10.1016/j.tet.2023.133379

  日期：2023.3

  Synthesis of an acidic pentasaccharide repeating unit corresponding to the cell wall O-antigen of the human pathogen, Providencia alcalifaciens O45:H25 strain has been achieved by multi-step stereoselective glycosylations. p-Methoxybenzyl (PMB) group was used as in situ removable protecting group, which was removed from the glycosylated products in the same pot after stereoselective glycosylations

  与人类病原体Providencia alcalifaciens O45:H25 菌株的细胞壁O抗原相对应的酸性五糖重复单元的合成已通过多步立体选择性糖基化实现。对甲氧基苄基 (PMB) 基团用作原位可去除保护基团，在立体选择性糖基化后在同一罐中从糖基化产物中去除。五糖衍生物中的 d-葡萄糖醛酸部分是通过使用后期 TEMPO-双（乙酰氧基）碘苯 (BAIB) 介导的选择性氧化将 d-葡萄糖部分的伯羟基转化为羧基而安装的健康）状况。只有硫糖苷供体用于糖基化步骤，具有令人满意的立体化学和化学产率。
• Concise synthesis of the tetrasaccharide repeating unit of the O-polysaccharide isolated from Edwardsiella tarda PCM 1156 strain
  作者：Rituparna Das、Mukul Mahanti、Balaram Mukhopadhyay

  DOI：10.1016/j.carres.2014.08.004

  日期：2014.11

  A convergent strategy has been developed for the synthesis of the tetrasaccharide repeating unit of the O-antigen from Edwardsiella tarda PCM 1156. Sequential glycosylations of a series of rationally protected monosaccharide intermediates were achieved either by the activation of thioglycosides using N-iodosuccinimide (NIS) in conjunction with H2SO4-silica or by activation of trichloroacetimidate by H2SO4-silica only. All glycosylation reactions resulted in the formation of the desired linkage with absolute stereoselectivity and yielded the required derivatives in good to excellent yields. Both azido and phthalimido groups have been used as the precursor of the desired acetamido group depending on the requirement of 1,2-cis- or 1,2-trans-glycosidic linkage. (C) 2014 Elsevier Ltd. All rights reserved.
• Stereoselective Synthesis of a Sulfated Tetrasaccharide Corresponding to a Rare Sequence in the Galactofucan Isolated from <i>Sargassum polycystum</i>
  作者：Jun Zhou、Liping Yang、Wenhao Hu

  DOI：10.1021/jo500503r

  日期：2014.5.16

  The first chemical synthesis of a highly sulfated tetrasaccharide 1, as the rare sequence in the galactofucan isolated from the brown alga Sargassum polycystum, was achieved in a convergent and stereoselective manner. The key features of the synthetic strategy include construction of multiple contiguous 1,2-cis glycosidic bonds and [2 + 2] assembly based on the rationally developed D-galactose building block 6. The synthesized oligosaccharides were fully characterized using a combination of coupled-HSQC and other 2D NMR techniques.
• Chemical synthesis of a tetrasaccharide related to the exocellular polysaccharide from Rhodococcus sp. RHA1
  作者：Darshita Budhadev、Balaram Mukhopadhyay

  DOI：10.1016/j.carres.2014.05.018

  日期：2014.7

  Chemical synthesis of the tetrasaccharide related to the exocellular polysaccharide from Rhodococcus sp. RHA1 is reported. The stereoselective glycosylations were achieved by activation of the thioglycoside donors using N-iodosuccinimide in the presence of La(OTf)(3) varying temperature per the need of 1,2-cis or 1,2-trans glycosylations. The target tetrasaccharide is reported in the form of its p-methoxyphenyl glycoside that can be cleaved selectively from the per-O-acetylated derivative allowing further glycoconjugate formation using trichloroacetimidate chemistry. (C) 2014 Elsevier Ltd. All rights reserved.