phenyl 3,4-O-isopropylidene-2-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranoside | 196397-63-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 3,4-O-isopropylidene-2-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranoside
• 英文别名: phenyl 3,4-O-isopropylidene-2-O-(4-methoxybenzyl)-1-thio-L-fucopyranoside；(3aR,4S,6R,7S,7aR)-7-[(4-methoxyphenyl)methoxy]-2,2,4-trimethyl-6-phenylsulfanyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran
• CAS: 196397-63-4
• 化学式: C₂₃H₂₈O₅S
• 分子量: 416.538
• InChiKey: UTKJMLWFEIBEQD-JBOLQRTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  71.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  phenyl 3,4-O-isopropylidene-2-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranoside 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 3.0h， 生成 phenyl 6-deoxy-2-(4-methoxybenzyl)-1-thio-β-L-galactopyranoside
  参考文献：
  名称：

  Synthesis of the glycan moiety of ganglioside HPG-7 with an unusual trimer of sialic acid as the inner sugar residue

  摘要：

  首次合成了从海参（Holothuria pervicax）中分离出来的神经节苷脂 HPG-7 的糖分子。为了达到不同的合成目的，我们特意利用适当区分的硅戊基单元构建了特有的亚结构，即嵌入聚糖中的三硅戊酸序列。最后，五糖作为己糖苷被成功传递。

  DOI：

  10.1039/c1cc13200h
• 作为产物：
  描述：

  2,3,4-三-O-乙酰基-6-脱氧-alpha-L-溴代半乳糖 在 对甲苯磺酸 氢氧化钾 、 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 乙醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 丙酮 、 乙腈 为溶剂， 反应 27.0h， 生成 phenyl 3,4-O-isopropylidene-2-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranoside
  参考文献：
  名称：

  Synthesis of Lewis X trisaccharide analogues in which glucose and rhamnose replace N-acetylglucosamine and fucose, respectively

  摘要：

  Two analogues of the Le(x) trisaccharide, alpha-L-Fucp -(1 --> 3)-[beta-D-Galp -(1 --> 4)]-D-Glcp were synthesized as allyl glycosides. In these derivatives either only the N-acetylglucosamine is replaced by glucose or both the N-acetylglucosamine and the facosyl residue are replaced by glucose and rhamnose, respectively. Our synthetic scheme used armed beta-thiophenyl fuco- and rhamnoside glycosyl donors that were prepared anomerically pure from the corresponding alpha-glycosyl bromides. The protecting groups were chosen to allow access to the fully deprotected trisaccharides without reduction of the allyl glycosidic group. These analogues will be used as soluble antigens in binding experiments with anti-Le(x) antibodies and can also be conjugated to a carrier protein and used as immunogens. In the course of this synthetic work, we also describe the use of reversed-phase HPLC to purify key protected trisaccharide intermediates prior to their deprotection. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00053-3

文献信息

• Synthesis of Asparagine Derivatives Harboring a Lewis X Type DC‐SIGN Ligand and Evaluation of their Impact on Immunomodulation in Multiple Sclerosis
  作者：Ward Doelman、Mikkel H. S. Marqvorsen、Fabrizio Chiodo、Sven C. M. Bruijns、Gijsbert A. Marel、Yvette Kooyk、Sander I. Kasteren、Can Araman

  DOI：10.1002/chem.202004076

  日期：2021.2.5

  Lewis‐type glycan structures in the N‐glycan of MOG with the DC‐SIGN receptor on dendritic cells (DCs). Here, we report the synthesis of an unnatural Lewis X (LeX)‐containing Fmoc‐SPPS‐compatible asparagine building block (SPPS=solid‐phase peptide synthesis), as well as asparagine building blocks containing two LeX‐derived oligosaccharides: LacNAc and Fucα1‐3GlcNAc. These building blocks were used for

  蛋白质髓磷脂少突胶质细胞糖蛋白（MOG）是髓磷脂的关键成分，也是疾病多发性硬化症（MS）中的自身抗原。MOG的Asn 31的翻译后N糖基化似乎在调节对髓磷脂的免疫反应中起关键作用。这是由MOG的N聚糖中的Lewis型聚糖结构与树突状细胞（DC）上的DC-SIGN受体相互作用所介导的。在这里，我们报告了一个非自然的路易斯X（Le X）包含的Fmoc-SPPS兼容天冬酰胺结构单元的合成（SPPS =固相肽合成），以及包含两个Le X的天冬酰胺结构单元的合成。衍生的寡糖：LacNAc和Fucα1-3GlcNAc。这些结构单元用于MOG免疫主要部分的糖基化（MOG 31-55），并分析了它们在不同生物学设置中与DC-SIGN结合的能力以及它们抑制瓜氨酸化诱导的聚集的能力MOG 31‐55中的内容。最后，在人单核细胞衍生的DC上进行了细胞因子分泌测定，结果表明，用单个Le X修饰的新糖肽具有改变促炎
• Synthesis of Lewis X trisaccharide analogues in which glucose and rhamnose replace N-acetylglucosamine and fucose, respectively
  作者：Ari Asnani、France-Isabelle Auzanneau

  DOI：10.1016/s0008-6215(03)00053-3

  日期：2003.5

  Two analogues of the Le(x) trisaccharide, alpha-L-Fucp -(1 --> 3)-[beta-D-Galp -(1 --> 4)]-D-Glcp were synthesized as allyl glycosides. In these derivatives either only the N-acetylglucosamine is replaced by glucose or both the N-acetylglucosamine and the facosyl residue are replaced by glucose and rhamnose, respectively. Our synthetic scheme used armed beta-thiophenyl fuco- and rhamnoside glycosyl donors that were prepared anomerically pure from the corresponding alpha-glycosyl bromides. The protecting groups were chosen to allow access to the fully deprotected trisaccharides without reduction of the allyl glycosidic group. These analogues will be used as soluble antigens in binding experiments with anti-Le(x) antibodies and can also be conjugated to a carrier protein and used as immunogens. In the course of this synthetic work, we also describe the use of reversed-phase HPLC to purify key protected trisaccharide intermediates prior to their deprotection. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Synthesis of the glycan moiety of ganglioside HPG-7 with an unusual trimer of sialic acid as the inner sugar residue
  作者：Yuki Iwayama、Hiromune Ando、Hide-Nori Tanaka、Hideharu Ishida、Makoto Kiso

  DOI：10.1039/c1cc13200h

  日期：——

  The glycan moiety of ganglioside HPG-7, isolated from the sea cucumber (Holothuria pervicax), was synthesized for the first time. The characteristic substructure, a trisialic acid sequence embedded in the glycan, was deliberately constructed by utilizing suitably differentiated sialyl units for various synthetic purposes. Finally, a pentasaccharide was successfully delivered as the hexyl glycoside.

  首次合成了从海参（Holothuria pervicax）中分离出来的神经节苷脂 HPG-7 的糖分子。为了达到不同的合成目的，我们特意利用适当区分的硅戊基单元构建了特有的亚结构，即嵌入聚糖中的三硅戊酸序列。最后，五糖作为己糖苷被成功传递。