1-bromo-2,3,4-tri-O-benzylfucopyranoside | 163059-64-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-bromo-2,3,4-tri-O-benzylfucopyranoside
• 英文别名: (2R,3S,4R,5R,6S)-2-bromo-6-methyl-3,4,5-tris(phenylmethoxy)oxane
• CAS: 163059-64-1
• 化学式: C₂₇H₂₉BrO₄
• 分子量: 497.429
• InChiKey: MJZXQAVNDOYDAP-FHEOWYEKSA-N

物化性质

• 沸点：
  564.8±50.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-bromo-2,3,4-tri-O-benzylfucopyranoside 在 4 A molecular sieve 、 camphor-10-sulfonic acid 、 四丁基溴化铵 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.58h， 生成 N-[(2S,3R,4R,5S,6R)-5-[[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy]-6-[[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxymethyl]-4-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-2-octoxyoxan-3-yl]acetamide
  参考文献：
  名称：

  Novel Disaccharide Inhibitors of Human Glioma Cell Division

  摘要：

  Several alpha-L-Fuc-(1-->3)-alpha-D-GlcNAcOC(8)H(17) disaccharide derivatives bearing different hydroxylated alkyl chains, with or without sulfate groups at C-4 and/or C-6 positions of the GlcNAc unit, have been synthesized and-tested as inhibitors of human astrocytoma Lines U-373 and U-118. The antimitotic activity was dependent on the structure and position of the hydroxylated chain linked to the disaccharide. The compounds with a pentaerythritol or L-glyceryl chain at the C-6 position showed the best inhibitory properties, with an ID50 value of ca. 200 mu M. On the contrary, sulfated disaccharide derivatives were inactive. The antimitotic activities of the compounds tested were essentially independent of the mitogen used to stimulate cell division.

  DOI：

  10.1021/jm980365i
• 作为产物：
  描述：

  (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol 在 吡啶 、 MeSiBr 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 1-bromo-2,3,4-tri-O-benzylfucopyranoside
  参考文献：
  名称：

  Oligosaccharides from "standardized intermediates." Synthesis of a branched tetrasaccharide glycoside related to the blood group B determinant

  摘要：

  DOI：

  10.1021/ja00389a061

文献信息

• [EN] HETEROBIFUNCTIONAL INHIBITORS OF E-SELECTIN AND GALECTIN-3<br/>[FR] INHIBITEURS HÉTÉROBIFONCTIONNELS DE E-SÉLECTINE ET DE GALECTINE -3
  申请人：GLYCOMIMETICS INC

  公开号：WO2019133878A1

  公开（公告）日：2019-07-04

  Compounds, compositions, and methods for treatment and/or prevention of at least one disease, disorder, and/or condition by inhibiting binding of an E-selectin, galectin-3, or E-selectin and galectin-3 to ligands are disclosed. For example, heterobifunctional inhibitors of E-selectin and galectin-3 are described and pharmaceutical compositions comprising at least one such agent is described.

  披露了用于治疗和/或预防至少一种疾病、紊乱和/或状况的化合物、组合物和方法，通过抑制E选择素、半乳糖凝集素-3或E选择素和半乳糖凝集素-3与配体的结合。例如，描述了E选择素和半乳糖凝集素-3的异双功能抑制剂，并描述了包含至少一种此类剂的药物组合物。
• PROCESS FOR PRODUCING 2'-O-FUCOSYLLACTOSE
  申请人：BASF SE

  公开号：US20210130384A1

  公开（公告）日：2021-05-06

  The present invention relates to a method for preparing 2′-O-fucosyllactose, the intermediates obtainable by this method and the use of these intermediates. The preparation comprises the reaction of a protected fucose of the general formula (I) with a tri(C 1 -C 6 -alkyl)silyl iodide to give a protected 1-iodofucose followed by the reaction of the protected 1-iodofucose with a compound of the general formula (II), in the presence of at least one base and deprotecting the resulting coupling product to afford 2′-O-fucosyllactose. In this context, the variables are each defined as follows: R a and R b are the same or different and are —C(═O)—C 1 -C 6 -alkyl, or —C(═O)-phenyl, wherein said phenyl is unsubstituted or optionally has 1 to 5 substituents, or R a and R b together are a radical —(C═O)— or a substituted methylene radical —C(R d R e )—, R c is a radical R Si or is benzyl, wherein said benzyl is unsubstituted or optionally has 1, 2 or 3 substituents, R Si is a radical of the formula SiR f R g R h , where R f , R g and R h are the same or different and are C 1 -C 8 -alkyl for example, R 1 is a radical —C(═O)—R 11 or a radical SiR 12 R 13 R 14 R 2 are the same or different and are C 1 -C 8 -alkyl for example; R 3 are the same or different and are for example C 1 -C 8 -alkyl or both radicals R 3 together form a linear C 1 -C 4 -alkenyl, which is unsubstituted or has 1 to 6 methyl groups as substituents.

  本发明涉及一种制备2'-O-岩藻糖乳的方法，以及通过该方法可获得的中间体和这些中间体的用途。该制备包括将一般式（I）的保护岩藻糖与三（C1-C6-烷基）硅基碘反应，得到保护1-碘岩藻糖，然后将保护1-碘岩藻糖与一般式（II）的化合物在至少一种碱的存在下反应，并去保护所得的偶联产物以得到2'-O-岩藻糖。在这种情况下，变量的定义如下：Ra和Rb相同或不同，为—C(═O)—C1-C6-烷基，或—C(═O)-苯基，其中所述苯基未取代或可选地具有1至5个取代基，或者Ra和Rb一起是一个基团—(C═O)—或一个取代亚甲基基团—C(RdRe)—，Rc是基团RSi或苄基，其中所述苄基未取代或可选地具有1、2或3个取代基，RSi是具有式SiRfRgRh的基团，其中Rf、Rg和Rh相同或不同，为C1-C8-烷基，例如，R1是基团—C(═O)—R11或基团SiR12R13R14，R2相同或不同，为C1-C8-烷基，例如，R3相同或不同，例如为C1-C8-烷基，或两个基团R3一起形成未取代或具有1至6个甲基基团作为取代基的线性C1-C4-烯基。
• Spijker, Nynke M.; Boeckel, Constant A. A. van, Angewandte Chemie, 1991, vol. 103, # 2, p. 179 - 182
  作者：Spijker, Nynke M.、Boeckel, Constant A. A. van

  DOI：——

  日期：——
• METHOD FOR PREPARING 2'-O-FUCOSYLLACTOSE
  申请人：BASF SE

  公开号：EP3191498B1

  公开（公告）日：2020-09-30
• VERFAHREN ZUR HERSTELLUNG VON 2'-O-FUCOSYLLACTOSE
  申请人：BASF SE

  公开号：EP3411379A1

  公开（公告）日：2018-12-12