ethyl [2,6-di-O-benzoyl-3,4-O-(1-methylethylidene)-β-D-galactopyranosyl]-(1->4)-2,3,6-tri-O-benzoyl-1-thio-β-D-glucopyranoside | 133411-30-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl [2,6-di-O-benzoyl-3,4-O-(1-methylethylidene)-β-D-galactopyranosyl]-(1->4)-2,3,6-tri-O-benzoyl-1-thio-β-D-glucopyranoside
• 英文别名: ethyl 2,3,6-tri-O-benzoyl-4-O-(2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside
• CAS: 133411-30-0
• 化学式: C₅₂H₅₀O₁₅S
• 分子量: 947.026
• InChiKey: WGJOWFDKDBACEC-ZKBJCVDUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.49
• 重原子数：
  68.0
• 可旋转键数：
  16.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  177.65
• 氢给体数：
  0.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  ethyl [2,6-di-O-benzoyl-3,4-O-(1-methylethylidene)-β-D-galactopyranosyl]-(1->4)-2,3,6-tri-O-benzoyl-1-thio-β-D-glucopyranoside 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 1.33h， 以79%的产率得到[2,6-di-O-benzoyl-3,4-O-(1-bromomethylethylidene)-β-D-galactopyranosyl]-(1->4)-2,3,6-tri-O-benzoyl-α-D-glucopyranosyl bromide
  参考文献：
  名称：

  Block Synthesis of Streptococcus pneumoniae Type 14 Capsular Polysaccharide Structures*

  摘要：

  Synthesis of a thioglycoside tetrasaccharide block, beta-D-Galp-(1 -> 4)-beta-DGlcp-(1 -> 6)-[beta-D-Galp-(1 -> 4)]-beta-D-GlcNPhthp-(1 -> SEt, corresponding to the repeating unit of Streptococcus pneumoniae serotype 14 CPS is described. Coupling of this block with a spacer followed by removal of an isopropylidene acetal yielded an acceptor, which was elongated with the donor block to give a protected dimer of the repeating unit. Iteration of this methodology yielded the trimer. Deprotection then produced an octa and a dode-casaccharide derivative ready for conjugation to proteins to afford immunoactive glycoconjugates.

  DOI：

  10.1081/car-200066935
• 作为产物：
  描述：

  苯甲酰氯 、 ethyl (3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-1-thio-β-D-glucopyranoside 在 吡啶 作用下， 反应 1.67h， 以96%的产率得到ethyl [2,6-di-O-benzoyl-3,4-O-(1-methylethylidene)-β-D-galactopyranosyl]-(1->4)-2,3,6-tri-O-benzoyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Block Synthesis of Streptococcus pneumoniae Type 14 Capsular Polysaccharide Structures*

  摘要：

  Synthesis of a thioglycoside tetrasaccharide block, beta-D-Galp-(1 -> 4)-beta-DGlcp-(1 -> 6)-[beta-D-Galp-(1 -> 4)]-beta-D-GlcNPhthp-(1 -> SEt, corresponding to the repeating unit of Streptococcus pneumoniae serotype 14 CPS is described. Coupling of this block with a spacer followed by removal of an isopropylidene acetal yielded an acceptor, which was elongated with the donor block to give a protected dimer of the repeating unit. Iteration of this methodology yielded the trimer. Deprotection then produced an octa and a dode-casaccharide derivative ready for conjugation to proteins to afford immunoactive glycoconjugates.

  DOI：

  10.1081/car-200066935

文献信息

• [EN] SYNTHETIC METHODS FOR THE LARGE SCALE PRODUCTION FROM GLUCOSE OF ANALOGS OF SPHINGOSINE, AZIDOSPHINGOSINE, CERAMIDES, LACTOSYL CERAMIDES, AND GLYCOSYL PHYTOSPHINGOSINE<br/>[FR] METHODES DE SYNTHESE PERMETTANT LA PRODUCTION A GRANDE ECHELLE A PARTIR DE GLUCOSE D'ANALOGUES DE SPHINGOSINE, AZIDOSPHINGOSINE, CERAMIDES, LACTOSYLCERAMIDES, ET GLYCOSYLE PHYTOSPHINGOSINE
  申请人：BUNDLE DAVID R

  公开号：WO2003101937A1

  公开（公告）日：2003-12-11

  Synthetic methods are disclosed for the production from glucose of analogs of sphingosine, azidosphingosine, ceramides, lactosyl ceramides, glycosyl phytosphingosine, and enantiomeric derivatives of phytosphingosine and/or its homologues, for use in pharmaceutical applications. The disclosed syntheses are simple, direct and easily scaled.

  揭示了一种从葡萄糖生产类似物的合成方法，包括鞘氨醇、偶氮鞘氨醇、酰胺、乳糖基酰胺、糖基植物鞘氨醇以及植物鞘氨醇及/或其同系物的对映体衍生物，用于药物应用。所揭示的合成方法简单、直接且易于扩展。
• 4-(Pyridin-2-yl)thiazol-2-yl thioglycosides as bidentate ligands for oligosaccharide synthesis via temporary deactivation
  作者：Papapida Pornsuriyasak、Nigam P. Rath、Alexei V. Demchenko

  DOI：10.1039/b810569c

  日期：——

  This study focusses on a new concept for oligosaccharide synthesis based on 4-(pyridin-2-yl)thiazol-2-yl thioglycosides that can either act as effective glycosyl donors or can be deactivated by stable bidentate complexation with palladium(II) bromide.

  本研究的重点是基于 4-(吡啶-2-基)噻唑-2-基硫代糖苷的寡糖合成新概念，这些硫代糖苷既可以作为有效的糖基供体，也可以通过与溴化钯（II）稳定的双叉络合物而失活。