phenyl 2,3-di-O-benzyl-4-O-(2-naphthyl)methyl-1-thio-β-L-fucopyranoside | 848416-63-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,3-di-O-benzyl-4-O-(2-naphthyl)methyl-1-thio-β-L-fucopyranoside
• 英文别名: (2S,3R,4R,5S,6R)-2-methyl-3-(naphthalen-2-ylmethoxy)-4,5-bis(phenylmethoxy)-6-phenylsulfanyloxane
• CAS: 848416-63-7
• 化学式: C₃₇H₃₆O₄S
• 分子量: 576.756
• InChiKey: RLPKXJQSLXUNQR-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 2,3-di-O-benzyl-4-O-(2-naphthyl)methyl-1-thio-β-L-fucopyranoside 在 4 A molecular sieve 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.33h， 生成 methyl 2,3-di-O-benzyl-α-L-fucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-β-D-galactopyranoside
  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
• 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 2,3-di-O-benzyl-4-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。