2,3,4-tri-O-benzyl-β-L-fucopyranose | 127875-50-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4-tri-O-benzyl-β-L-fucopyranose
• 英文别名: (2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-ol
• CAS: 127875-50-7
• 化学式: C₂₇H₃₀O₅
• 分子量: 434.532
• InChiKey: YRAQXZMHYZXWBZ-FHEOWYEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  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：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  allyl α-L-fucopyranoside 在 potassium tert-butylate 、 碘 、 sodium hydride 、 碳酸氢钠 作用下， 以 四氢呋喃 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.25h， 生成 2,3,4-tri-O-benzyl-β-L-fucopyranose
  参考文献：
  名称：

  Synthesis, NMR and Conformational Studies of Fucoidan Fragments 1:¹Desulfated 2,3- and 3,4-Branched Trisaccharide Fragments and Constituting Disaccharides

  摘要：

  Two fucotriosides with vicinal disubstitution alpha -L-Fuc-(1-->2)[alpha -L-Fuc-(1-->3)[alpha -L-Fuc-OPr (1) and alpha -L-Fuc-(1-->3)[alpha -L-Fuc-(1-->4)]alpha -L-Fuc-OPr (2), which are related to fragments of natural polysaccharides fucoidans, have been synthesized together with constituent disaccharides 3-5, Spectral and conformational properties of tri- and disaccharides have been investigated by (1)H, (13)C and NOE NMR spectroscopy.

  DOI：

  10.1080/07328300008544140

文献信息

• Sweet (hetero)aromatics: glycosylated templates for the construction of saccharide mimetics
  作者：Christine Wiebe、Claudine Schlemmer、Stefan Weck、Till Opatz

  DOI：10.1039/c1cc13078a

  日期：——

  Mono- and diglycosylated aromatics and heteroaromatics may serve as building blocks for the construction of metabolically stable mimetics of oligosaccharides. Methods for their preparation from monosaccharidic precursors by direct C-glycosylation, dipolar cycloaddition or Larock cyclization are described.

  单糖基和二糖基修饰的芳香化合物和杂芳香化合物可作为构建代谢稳定的低聚糖模拟物的砌块。本文描述了通过直接C-糖基化、偶极环加成或Larock环化反应从单糖前体合成这些化合物的方法。
• New Method for Regioselective Glycosylation Employing Saccharide Oxyanions
  作者：Martin Matwiejuk、Joachim Thiem

  DOI：10.1002/ejoc.201100861

  日期：2011.10

  As an alternative concept for glycosylation, the prior activation of acceptor hydroxy groups for selective glycosidic bond formation, was investigated to give complex oligosaccharides. Oxyanions obtained from partially protected saccharides were glycosylated by employing glycopyranosyl halides, and the regiochemical results were studied. Initially, partially methylated methyl-α-D-glucopyranosides were

  作为糖基化的替代概念，研究了先激活受体羟基以形成选择性糖苷键，以得到复杂的寡糖。从部分保护的糖类中获得的氧阴离子通过使用吡喃糖基卤化物进行糖基化，并研究了区域化学结果。最初，部分甲基化的甲基-α-D-吡喃葡萄糖苷被用作模型系统来研究碱基促进糖基化的基本机制原理。实现了高区域选择性和立体特异性糖苷键的形成，并且该方法的范围通过不同的全苄化糖基供体进行了扩展。
• Synthesis of Phenolic Glycosides: Glycosylation of Sugar Lactols with Aryl Bromides via Dual Photoredox/Ni Catalysis
  作者：Hui Ye、Cong Xiao、Quan-Quan Zhou、Peng George Wang、Wen-Jing Xiao

  DOI：10.1021/acs.joc.8b02129

  日期：2018.11.2

  Multifarious sugar lactols were efficiently transformed into the corresponding phenolic glycosides by treating with aryl bromides in acetonitrile with Ir[dF(CF3)ppy]2(dtbbpy)(PF6) as a photocatalyst under visible light irradiation. Both pyranoses and furanoses or even disaccharide could all suffer this glycosylation protocol under mild reaction conditions. A variety of phenyl glycosides can be produced

  通过在可见光下用Ir [dF（CF 3）ppy] 2（dtbbpy）（PF 6）作为光催化剂在乙腈中用芳基溴化物处理，将多种糖乳糖醇有效地转化为相应的酚类糖苷。在温和的反应条件下，吡喃糖酶和呋喃糖酶甚至二糖都可能遭受这种糖基化方案的影响。可以以中等到良好的产率（高达93％的产率）生产各种苯基糖苷，并且该方案的克级工艺也得到了很好的确立。
• 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。
• <i>N</i>-Bromosuccinimide-Mediated Conversion of Allyl Glycosides to Glycosyl Hemiacetals
  作者：Rajib Panchadhayee、Anup Kumar Misra

  DOI：10.1080/07328301003664887

  日期：2010.3.22

  A novel reaction condition has been developed for the hydrolysis of differentially functionalized allyl glycosides to their corresponding glycosyl hemiacetal derivatives in the presence of N-bromosuccinimide (NBS). The reaction condition is exceptionally fast, mild, and compatible with most of the functional groups used in the oligosaccharide synthesis, and yields were excellent.

  在N-溴代琥珀酰亚胺（NBS）存在下，已经开发出了一种新的反应条件，用于将不同功能化的烯丙基糖苷水解为它们相应的糖基半缩醛衍生物。反应条件异常快速，温和，并且与寡糖合成中使用的大多数官能团相容，并且收率非常好。