4-chlorophenyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside | 296768-93-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 4-chlorophenyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
• 英文别名: p-chlorophenyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside；2-[(2R,4aR,6S,7R,8R,8aS)-6-(4-chlorophenyl)sulfanyl-8-hydroxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]isoindole-1,3-dione
• CAS: 296768-93-9
• 化学式: C₂₇H₂₂ClNO₆S
• 分子量: 523.994
• InChiKey: BSNSURFMWOVPGA-FZZOYGMESA-N

物化性质

• 沸点：
  726.1±60.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  36
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-chlorophenyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 在 吡啶 、 三乙基硅烷 、 三氟化硼乙醚 、 sodium hydride 、 碳酸氢钠 、 乙二胺 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 5.5h， 生成 p-chlorophenyl 2-acetamido-4-O-acetyl-6-O-benzyl-2-deoxy-2,3-N,O-carbonyl-1-thio-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a Forssman antigen derivative for use in a conjugate vaccine

  摘要：

  The total chemical synthesis of a Forssman antigen analog is described. The pentasaccharide contains a functionalized tether which should facilitate future conjugation with immunogenic proteins. We found that the total synthesis can be efficiently achieved by following a convergent 2+3 strategy, and using N-Troc protected GalNAc thioglycoside as a donor. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.09.015
• 作为产物：
  描述：

  2-脱氧-2-苯二酰亚胺-1,3,4,6-四-氧-乙酰-β-D-吡喃葡萄糖 在 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 4-chlorophenyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  由芳基/烷基硫代糖苷方便地制备糖基氯。

  摘要：

  [反应：见正文]由于糖生物学领域中存在巨大的结构多样性，正交寡糖组装的通用方法一直是人们所关注的。本文报道的是通过相应的硫代糖苷前体与氯氯化物试剂4反应获得的糖基氯化物供体的制备。如此获得的粗氯化物可直接用于随后的糖基化反应中，并且提供了该方法的一般性实例。

  DOI：

  10.1021/ol0063050

文献信息

• Total synthesis of Myc-IV(C16:0, S) via automated electrochemical assembly
  作者：Kumpei Yano、Toshiyuki Itoh、Toshiki Nokami

  DOI：10.1016/j.carres.2020.108018

  日期：2020.6

  Total synthesis of Myc-IV(C16:0, S) via automated electrochemical assembly has been accomplished. This tetrasaccharide has been studied as a symbiotic signal molecule of Arbuscular Mycorrhiza fungi. We have achieved stereoselective synthesis of a disaccharide building block using the mixed-electrolyte system for electrochemical glycosylation; 2 + 1+1 strategy enables us to access the tetrasaccharide

  通过自动电化学组装完成Myc-IV（C16：0，S）的全合成。已经研究了这种四糖作为丛枝菌根真菌的共生信号分子。我们已经使用用于电化学糖基化的混合电解质系统实现了二糖结构单元的立体选择性合成；2 + 1 + 1策略使我们能够访问四糖前体并有效地完成Myc-IV（C16：0，S）的合成。
• Total synthesis of LeA-LacNAc pentasaccharide as a ligand for Clostridium difficiletoxin A
  作者：Ping Zhang、Kenneth Ng、Chang-Chun Ling

  DOI：10.1039/b914193f

  日期：——

  The toxins TcdA and TcdB produced by the human pathogen Clostridium difficile gain entrance to host epithelial cells by recognizing cell-surface carbohydrate ligands. Inhibiting the attachment of these toxins to host cells has been proposed to be a viable therapy to treat C. difficile infections. Glycan array screening previously revealed that the LeA-LacNAc pentasaccharide binds strongly to TcdA. Here we report the efficient syntheses of the pentasaccharide and a structurally related tetrasaccharide motif. These compounds will be used to better define the carbohydrate-binding specificity of toxins from C. difficile, which will hopefully lead to the development of improved therapeutics.

  人类病原体艰难梭菌产生的毒素 TcdA 和 TcdB 通过识别细胞表面碳水化合物配体进入宿主上皮细胞。抑制这些毒素附着在宿主细胞上被认为是治疗艰难梭菌感染的一种可行疗法。之前的糖阵列筛选显示，LeA-LacNAc 五糖与 TcdA 有很强的结合力。在此，我们报告了五糖和结构相关的四糖的高效合成。这些化合物将用于更好地确定艰难梭菌毒素的碳水化合物结合特异性，从而有望开发出更好的疗法。
• A Scalable Approach to Obtaining Orthogonally Protected β-<scp>d</scp>-Idopyranosides
  作者：Rachel Hevey、Alizée Morland、Chang-Chun Ling

  DOI：10.1021/jo300764k

  日期：2012.8.17

  A practical method to obtain orthogonally protected D-idopyranose from D-galactose has been developed, which is the first method to enable synthesis of the challenging beta-D-idopyranoside linkage. The method relies on a key double inversion at O-2 and O-3 in an easily prepared D-galactose derivative, which proceeds regio- and stereoselectively through a 2,3-anhydrotalopyranoside; reaction using a selection of alkoxides affords exclusively the 3-O-alkylidopyranoside, which can be used to generate an orthogonally protected monosaccharide. The process is scalable and requires minimal purification, so it could be used to produce building blocks to aid in the synthesis of various beta-idopyranose-containing oligosaccharide targets to further probe their biological functions.
• US2023/143273
  申请人：——

  公开号：——

  公开（公告）日：——
• A Convenient Preparation of Glycosyl Chlorides from Aryl/Alkyl Thioglycosides
  作者：Shin Sugiyama、James M. Diakur

  DOI：10.1021/ol0063050

  日期：2000.8.1

  see text]Because of the vast structural diversity encountered in the field of glycobiology, versatile methods for orthogonal oligosaccharide assembly are always of interest. Reported herein is the preparation of glycosyl chloride donors obtained by reaction of the corresponding thioglycoside precursors with chlorosulfonium chloride reagent 4. The crude chlorides thus obtained can be used directly in subsequent

  [反应：见正文]由于糖生物学领域中存在巨大的结构多样性，正交寡糖组装的通用方法一直是人们所关注的。本文报道的是通过相应的硫代糖苷前体与氯氯化物试剂4反应获得的糖基氯化物供体的制备。如此获得的粗氯化物可直接用于随后的糖基化反应中，并且提供了该方法的一般性实例。