3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)propanoic acid | 140909-65-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)propanoic acid
• 英文别名: 3-[(2R,3R,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]propanoic acid
• CAS: 140909-65-5
• 化学式: C₃₇H₄₀O₇
• 分子量: 596.72
• InChiKey: SIOBNHSBZPHQRM-MUMOPMNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  44
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)propanoic acid 在 4-二甲氨基吡啶 、 乙二醇二甲醚溴化镍 、 N-羟基邻苯二甲酰亚胺 、 N,N'-二异丙基碳二亚胺 、 锌 、 2,6-双(4,5-二氢噁唑-2-基)吡啶 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 18.5h， 生成
  参考文献：
  名称：

  Ti催化立体选择性糖基自由基功能化合成C-糖苷

  摘要：

  C-烷基糖苷在自然界中广泛存在，由于其多种药用特性，在药物开发计划中不可或缺。以前的合成工作通常使用化学计量试剂，而提供此类糖苷的催化方法的范围有限。在这里，我们描述了一种立体选择性 Ti 催化方案，该方案通过立体控制的糖基自由基加成来有效地将大量容易获得的糖基氯与活化的烯烃合并，以提供各种C-烷基糖苷。通过使用炔烃作为自由基受体，本策略适用于合成带有Z的C-烯基糖苷烯烃附属物。通过机械和计算研究阐明了在有机钛络合物存在下糖基氯（与简单的叔氯烷烃相比）出乎意料的更大反应性。治疗上重要的碳水化合物和糖肽缀合物的简明制备强调了该协议的实用性，这些碳水化合物和糖肽缀合物很难使用替代方法获得。

  DOI：

  10.1016/j.chempr.2021.09.008
• 作为产物：
  描述：

  3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)propene 在 sodium hydroxide 、 sodium chlorite 、 potassium dihydrogenphosphate 、 9-borabicyclo[3.3.1]nonane dimer 、 2-甲基-2-丁烯 、 草酰氯 、 双氧水 、 二甲基亚砜 、 三乙胺 作用下， 以 水 、 叔丁醇 为溶剂， 生成 3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)propanoic acid
  参考文献：
  名称：

  通过烯烃复分解聚合制备1,6-连接的C-二糖

  摘要：

  3,4,6-三-O-苄基-1,2-二脱氧-d-阿拉伯糖基-己-1-烯醇（5a）与多种糖基羧酸6a-d的DCC介导的偶联反应得到酯7a -d的产量高。形成的酯的亚甲基化导致无环烯醇醚8a-d，并在盒子中在温暖的甲苯中暴露于Schrock钼催化剂1中，以良好的产率得到目标C-二糖二醇9a-d。将1，6-连接的基于葡萄糖的C-二糖聚糖9a转化为2-脱氧-β-葡萄糖衍生物10a以及相应的葡萄糖β-葡萄糖-C-二糖13。

  DOI：

  10.1016/s0040-4039(99)00815-1

文献信息

• Differential Carbohydrate Recognition of Two GlcNAc-6-sulfotransferases with Possible Roles in L-Selectin Ligand Biosynthesis
  作者：Brian N. Cook、Sunil Bhakta、Teresa Biegel、Kendra G. Bowman、Joshua I. Armstrong、Stefan Hemmerich、Carolyn R. Bertozzi

  DOI：10.1021/ja001224k

  日期：2000.9.1

  Two human GlcNAc-6-sulfotransferases, CHST2 and HEC-GlcNAc6ST, have been recently identified as possible contributors to the inflammatory response by virtue of their participation in L-selectin ligand biosynthesis. Selective inhibitors would facilitate their functional elucidation and might provide leads for antiinflammatory therapy. Here we investigate the critical elements of a disaccharide substrate that are required for recognition by CHST2 and HEC-GlcNAc6ST. A panel of disaccharide analogues, bearing modifications to the pyranose rings and aglycon substituents, were synthesized and screened for substrate activity with each enzyme. Both GlcNAc-6-sulfotransferases required the 2-N-acetamido and 4-hydroxyl groups of a terminal GlcNAc residue for conversion to product. Both enzymes tolerated modifications to the reducing terminal pyranose. Key differences in recognition of an amide group in the aglycon substituent were observed, providing the basis for future glycomimetic inhibitor design.
• Adaptable Synthesis of <i>C</i>-Glycosidic Multivalent Carbohydrates and Succinamide-Linked Derivatization
  作者：Gavin J. Miller、John M. Gardiner

  DOI：10.1021/ol102310x

  日期：2010.11.19

  A modular approach to the synthesis of trivalent C-glycosidic carbohydrates is described. The approach is illustrated employing carboxylate-terminated C-glycosidic D-mannose, D-glucose, and D-galactose derivatives with different length C1-linked spacer units and also core units with different length linker units attached. The central core scaffold is additionally functionalized via a succinamide-based, conjugatable linker unit, exemplified in an extended multivalent derivative [31] and a pyrene-bearing fluorsecent-labeled tris-C-mannosyl conjugate [33].
• C-glycosyl compounds bind to receptors on the surface of Escherichia coli and can target proteins to the organism
  作者：Carolyn Bertozzi、Mark Bednarski

  DOI：10.1016/0008-6215(92)80021-r

  日期：1992.1

  A series of C-mannopyranosyl derivatives have been synthesized and their inhibitory activity towards the receptor-mediated adhesion of E. coli to yeast cells has been tested. Total inhibition of yeast-cell agglutination by C-glycosyl derivatives 4 and 9 is achieved at a concentration approximately one order of magnitude lower than that of methyl alpha-D-mannopyranoside, indicating that the binding affinity to the receptor is related to the hydrophobicity of the carbon-linked side chain. A biotin-linked C-glycosyl derivative of mannose (compound 9) has been synthesized and used to target avidin and streptavidin to the bacterial cell surface. Of the C-glycosyl derivatives tested in our study, the conjugate of compound 9 with avidin had the highest avidity for the bacterial receptors, inhibiting agglutination at a concentration three orders of magnitude lower than methyl alpha-D-mannopyranoside. The use of such bifunctional compounds as the mannose-biotin conjugate 9 is a general strategy to target molecules to pathogenic organisms via their cell-surface carbohydrate receptors and to change the antigenicity of the bacterial cell surface.