phenyl 3,4-O-isopropilidene-1-thio-β-L-fucopyranoside | 196397-59-8

• 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-isopropilidene-1-thio-β-L-fucopyranoside
• 英文别名: phenyl 3,4-O-isopropylidene-1-thio-β-L-fucopyranoside；(3aR,4S,6R,7S,7aS)-2,2,4-trimethyl-6-phenylsulfanyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol
• CAS: 196397-59-8
• 化学式: C₁₅H₂₀O₄S
• 分子量: 296.387
• InChiKey: DRFWACUWILJLLY-FRVYIDGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  73.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  phenyl 3,4-O-isopropilidene-1-thio-β-L-fucopyranoside 在 盐酸 、 sodium hydride 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 phenyl 2-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
• 作为产物：
  描述：

  phenyl 2,3,4-tri-O-acetyl-1-thio-L-fucopyranoside 在 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 48.0h， 生成 phenyl 3,4-O-isopropilidene-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

• Total synthesis of trifluorobutyryl-modified, protected sialyl Lewis X by a convergent [2+2] approach
  作者：Gizem Akçay、John Y. Ramphal、Marc d’Alarcao、Krishna Kumar

  DOI：10.1016/j.tetlet.2014.11.029

  日期：2015.1

  adhesion of mammalian cells to E and P-Selectin, presumably by leading to the expression of fluorinated sLex epitopes on cell surfaces, and interfering with the sLex–selectin interactions that are well known in mediating tumour cell migration (J. Med. Chem. 2010, 53, 4277). For studies directed towards understanding the molecular basis of this reduced adhesion, chemical synthesis of trifluorobutyrylated

  真核细胞表面唾液酸残基表达的结构和数量变化深刻影响着广泛的生物学过程，包括炎症，抗原识别，微生物附着和肿瘤转移。唾液酸类似物的摄取和在哺乳动物细胞中的掺入可以进行结构功能研究和特定识别事件的扰动。我们的小组最近表明，三氟丁酰修饰的唾液酸代谢产物可降低哺乳动物细胞对E和P-选择素的粘附力，大概是通过导致细胞表面上氟化的sLe x表位的表达，并干扰sLe x-选择素的相互作用。在介导肿瘤细胞迁移中众所周知的（J.Med.Chem。 2010，53，4277）。对于旨在理解这种降低的粘附力的分子基础的研究，三氟丁酰化唾液酸路易斯X（C 4 F 3 -sLe x）的化学合成至关重要。我们已经开发了一种高效的[2 + 2]方法，可用于制备规模的C 4 F 3 -sLe x，该方法包含通用的保护基，可以根据生物物理研究的需要，将聚糖表面固定或增溶，以研究选择素的相互作用。 。原则上，该策略可用于制备其他N-修饰的sLe
• A first synthesis of sulfonic acid analogues of N-acetylneuraminic acid
  作者：Zoltán B. Szabó、Anikó Borbás、István Bajza、András Lipták、Sándor Antus

  DOI：10.1016/j.tetlet.2007.12.043

  日期：2008.2

  Sulfonic acid analogues of N-acetylneuraminic are synthesized from 1-thio-l-fucoside derivatives with the introduction of an azido group at C-4 of the fucose moiety and carbanionic addition onto fully protected lactones. The analogues in the form of methyl glycosides are subjected to a neuraminidase inhibition assay.

  N-乙酰神经氨酸的磺酸类似物是由1-硫-1-岩藻糖苷衍生物合成的，在岩藻糖部分的C-4处引入叠氮基，并将碳负离子加成至完全保护的内酯上。对甲基糖苷形式的类似物进行神经氨酸酶抑制测定。
• METHOD FOR THE SYNTHESIS OF A TRISACCHARIDE
  申请人：Dékany Gyula

  公开号：US20130131334A1

  公开（公告）日：2013-05-23

  The present invention relates to an improved synthesis of a trisaccharide of the formula (1), novel intermediates used in the synthesis and the preparation of the intermediates.

  本发明涉及一种改进的合成方法，用于合成式（1）的三糖，以及在合成过程中使用的新型中间体和中间体的制备。
• [EN] SYNTHESIS OF 2'-O-FUCOSYLLACTOSE<br/>[FR] SYNTHÈSE DE 2'-O-FUCOSYLLACTOSE
  申请人：GLYCOM AS

  公开号：WO2010115934A1

  公开（公告）日：2010-10-14

  The present invention relates to an improved synthesis of a trisaccharide of the formula (1), novel intermediates used in the synthesis and the preparation of the intermediates.

  本发明涉及改进的三糖的合成方法，所述三糖的化学式为（1），以及合成过程中使用的新型中间体和中间体的制备。
• [EN] SYNTHESIS OF 2 ' -O-FUCOSYLLACTOSE<br/>[FR] SYNTHÈSE DE 2'-O-FUSOSYLLACTOSE
  申请人：GLYCOM AS

  公开号：WO2010115935A1

  公开（公告）日：2010-10-14

  The present invention relates to an improved synthesis of a trisaccharide of the formula, novel intermediates used in the synthesis and the preparation of the intermediates.

  本发明涉及一种改进的三糖的合成方法，以及用于合成的新型中间体和中间体的制备。