phenyl 2,4-di-O-benzyl-3-O-(2-naphthyl)methyl-1-thio-β-L-fucopyranoside | 848416-62-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,4-di-O-benzyl-3-O-(2-naphthyl)methyl-1-thio-β-L-fucopyranoside
• 英文别名: (2S,3R,4R,5S,6R)-2-methyl-4-(naphthalen-2-ylmethoxy)-3,5-bis(phenylmethoxy)-6-phenylsulfanyloxane
• CAS: 848416-62-6
• 化学式: C₃₇H₃₆O₄S
• 分子量: 576.756
• InChiKey: SCIDCFSHLQMMNZ-XMXAXWGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  42
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  62.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  phenyl 2,4-di-O-benzyl-3-O-(2-naphthyl)methyl-1-thio-β-L-fucopyranoside 在 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 、 三氟乙酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 7.0h， 生成 3-O-acetyl-2,4-di-O-benzyl-L-fucopyranose
  参考文献：
  名称：

  肺炎克雷伯菌的荚膜多糖三糖重复单元的合成

  摘要：

  全球范围内，由肺炎克雷伯菌引起的原发性发热性肝脓肿并发脑膜炎和败血性眼内炎的发生率有所增加。早期研究表明，肺炎克雷伯菌的荚膜多糖（CPS）在抗吞噬作用和相关的致病性中起重要作用。该CPS的三糖重复单元的第一化学合成是通过具有正交和适当保护基的立体选择性糖基化实现的。开发了一种反式丙酮酸丙酮化的新方法。

  DOI：

  10.1016/j.tetlet.2018.12.031
• 作为产物：
  描述：

  phenyl 2,3,4-tri-O-acetyl-1-thio-L-fucopyranoside 在 lithium aluminium tetrahydride 、 三氯化铝 、 D(+)-10-樟脑磺酸 、 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 171.25h， 生成 phenyl 2,4-di-O-benzyl-3-O-(2-naphthyl)methyl-1-thio-β-L-fucopyranoside
  参考文献：
  名称：

  Synthesis of fully protected α-l-fucopyranosyl-(1→2)-β-d-galactopyranosides with a single free hydroxy group at position 2′, 3′ or 4′ using O-(2-naphthyl)methyl (NAP) ether as a temporary protecting group

  摘要：

  Perbenzylated methyl alpha-L-fucopyranosyl-(1-->2)-beta-D-galactopyranosides having a single free OH group at position C-2'. C-3' or C-4' have been synthesized. Methyl 3,4,6-tri-O-benzyl-beta-D-galactopyranoside was glyco-sylated either with phenyl 3,4-di-O-benzyl-2-O-(2-naphthyl)-methyl-, phenyl 2,4-di-O-benzyl-3-O-(2-naphthyl)methyl- or phenyl 2,3-di-O-benzyl-4-O-(2-naphthyl)methyl-1-thio-beta-L-fucopyranoside. The 2-ONAP ether functioned well as a non-participating group. The yields of the glycosylation reactions, promoted by NIS/TfOH, were above 80% and the stereoselectivity was 8:1 to 10:1 in favour of the alpha-anomers. The 2-ONAP ether was obtained by (2-naphthyl)methylation, the 3-ONAP and the 4-ONAP ethers were prepared either by hydrogenolysis of the 3,4-O-(2-naphthyl)methylene acetals of beta-L-fucopyranoside or by tin acetal-mediated alkylations. The latter procedure afforded higher yields. The ONAP ethers from the disaccharides were removed by oxidative cleavage with DDQ. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.056

文献信息

• Synthesis of three regioisomers of the pentasaccharide part of the Skp1 glycoprotein of Dictyostelium discoideum
  作者：Zoltán B. Szabó、Mihály Herczeg、Anikó Fekete、Gyula Batta、Anikó Borbás、András Lipták、Sándor Antus

  DOI：10.1016/j.tetasy.2009.02.040

  日期：2009.5

  the form of (2-trimethylsilyl)ethyl glycosides by means of 2+3 block syntheses using the disaccharide donor at the non-reducing end, and three different trisaccharide acceptors at the reducing end. Fucosylation of (2-trimethylsilyl)ethyl 3,4,6-tri-O-benzyl-β-d-galactopyranosyl-(1→3)-4,6-O-benzylidene-2-deoxy-2-NPhth-β-d-glucopyranoside with different fucosyl donors carrying an O-(2-naphthyl)methyl ether

  在盘基网柄菌中发现了Skp1糖蛋白的线性五糖部分的三种区域异构体，通过（2-三甲基甲硅烷基）乙基糖苷的形式，通过在非还原端使用二糖供体进行2 + 3嵌段合成，以及在还原端有三个不同的三糖受体。（2-三甲基硅烷基）乙基3,4,6-三-岩藻糖基ö苄基β-d吡喃半乳糖- （1→3）-4,6- Ô -亚苄基-2-脱氧-2- Ñ PHTH-β -d-吡喃葡萄糖苷与不同的岩藻糖基供体携带O在位置C2，C3或C4处作为临时保护基的-（2-萘基）甲基醚产生了被保护的核心三糖。在选择性除去（2-萘基）甲基之后，将所得的受体用α（1→6）连接的二半乳糖基供体糖基化，以产生相应的三种区域异构的五糖。将邻苯二甲酰亚胺基部分转化为N-乙酰基，然后对可还原保护基进行催化氢化，得到了游离的目标五糖，在阐明天然五糖的确切结构时，它应该能够提供帮助。
• Synthesis of the trisaccharide repeating unit of capsular polysaccharide from Klebsiella pneumoniae
  作者：Woen Susanto、Kah-Hoe Kong、Kuo-Feng Hua、Shih-Hsiung Wu、Yulin Lam

  DOI：10.1016/j.tetlet.2018.12.031

  日期：2019.1

  have shown that the capsular polysaccharide (CPS) of Klebsiella pneumoniae plays an important role in the resistance to phagocytosis and related pathogenicity. The first chemical synthesis of the trisaccharide repeating unit of this CPS has been achieved via stereoselective glycosylation with orthogonal and appropriate protecting groups. A new method for the pyruvylation of trans diol was developed.

  全球范围内，由肺炎克雷伯菌引起的原发性发热性肝脓肿并发脑膜炎和败血性眼内炎的发生率有所增加。早期研究表明，肺炎克雷伯菌的荚膜多糖（CPS）在抗吞噬作用和相关的致病性中起重要作用。该CPS的三糖重复单元的第一化学合成是通过具有正交和适当保护基的立体选择性糖基化实现的。开发了一种反式丙酮酸丙酮化的新方法。
• Synthesis of fully protected α-l-fucopyranosyl-(1→2)-β-d-galactopyranosides with a single free hydroxy group at position 2′, 3′ or 4′ using O-(2-naphthyl)methyl (NAP) ether as a temporary protecting group
  作者：Zoltán B. Szabó、Anikó Borbás、István Bajza、András Lipták

  DOI：10.1016/j.tetasy.2004.11.056

  日期：2005.1

  Perbenzylated methyl alpha-L-fucopyranosyl-(1-->2)-beta-D-galactopyranosides having a single free OH group at position C-2'. C-3' or C-4' have been synthesized. Methyl 3,4,6-tri-O-benzyl-beta-D-galactopyranoside was glyco-sylated either with phenyl 3,4-di-O-benzyl-2-O-(2-naphthyl)-methyl-, phenyl 2,4-di-O-benzyl-3-O-(2-naphthyl)methyl- or phenyl 2,3-di-O-benzyl-4-O-(2-naphthyl)methyl-1-thio-beta-L-fucopyranoside. The 2-ONAP ether functioned well as a non-participating group. The yields of the glycosylation reactions, promoted by NIS/TfOH, were above 80% and the stereoselectivity was 8:1 to 10:1 in favour of the alpha-anomers. The 2-ONAP ether was obtained by (2-naphthyl)methylation, the 3-ONAP and the 4-ONAP ethers were prepared either by hydrogenolysis of the 3,4-O-(2-naphthyl)methylene acetals of beta-L-fucopyranoside or by tin acetal-mediated alkylations. The latter procedure afforded higher yields. The ONAP ethers from the disaccharides were removed by oxidative cleavage with DDQ. (C) 2004 Elsevier Ltd. All rights reserved.