(3S,4S,5S,6R)-2-ethylsulfanyl-6-(hydroxymethyl)oxane-3,4,5-triol | 1080665-72-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,4S,5S,6R)-2-ethylsulfanyl-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1080665-72-0
• 化学式: C₈H₁₆O₅S
• 分子量: 224.278
• InChiKey: CHAHFVCHPSPXOE-WZPXOXCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  115
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3S,4S,5S,6R)-2-ethylsulfanyl-6-(hydroxymethyl)oxane-3,4,5-triol 在 吡啶 、 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 对甲苯磺酸 、 N,N'-二异丙基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 [(2R,3R,4S,5S,6R)-4,5-dibenzoyloxy-6-dibutoxyphosphoryloxy-2-[6-(9H-fluoren-9-ylmethoxycarbonylamino)hexanoyloxymethyl]oxan-3-yl] benzoate
  参考文献：
  名称：

  自动化的多糖合成：30mer甘露糖苷的组装

  摘要：

  自动化的碳水化合物合成开辟了新天地：迄今为止，化学合成最长的糖（30 mer）已经获得。该过程的关键是使用释放释放技术，该技术可以标记糖，从而可以通过暂时附着在磁性颗粒上而将其分离。

  DOI：

  10.1002/anie.201210176
• 作为产物：
  描述：

  Acetic acid (2R,3R,4S,5S)-3,5-diacetoxy-2-acetoxymethyl-6-ethylsulfanyl-tetrahydro-pyran-4-yl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 (3S,4S,5S,6R)-2-ethylsulfanyl-6-(hydroxymethyl)oxane-3,4,5-triol
  参考文献：
  名称：

  自动化的多糖合成：30mer甘露糖苷的组装

  摘要：

  自动化的碳水化合物合成开辟了新天地：迄今为止，化学合成最长的糖（30 mer）已经获得。该过程的关键是使用释放释放技术，该技术可以标记糖，从而可以通过暂时附着在磁性颗粒上而将其分离。

  DOI：

  10.1002/anie.201210176

文献信息

• METHOD FOR PREPARING C-6 PHOSPHORYLATED D-ALDOHEXOSES AND C-6 PHOSPHORYLATED D-ALDOHEXOSE DERIVATIVES, AND NEW C-6 PHOSPHORYLATED D-ALDOHEXOSE DERIVATIVES
  申请人：Libragen

  公开号：EP2150620A2

  公开（公告）日：2010-02-10
• Method for preparing C-6 phosphorylated D-aldohexoses and C-6 phosphorylated D-aldohexose derivatives, and new C-6 phosphorylated D-aldohexose derivatives
  申请人：Libragen

  公开号：EP2150620B1

  公开（公告）日：2011-08-10
• [EN] METHOD FOR PREPARING C-6 PHOSPHORYLATED D-ALDOHEXOSES AND C-6 PHOSPHORYLATED D-ALDOHEXOSES DERIVATIVES AND NEW C-6 PHOSPHORYLATED D-ALDOHEXOSES DERIVATIVES<br/>[FR] PROCÉDÉ DE PRÉPARATION DE D-ALDOHEXOSES C-6 PHOSPHORYLÉES ET DE DÉRIVÉS DE D-ALDOHEXOSES C-6 PHOSPHORYLÉES ET NOUVEAUX DÉRIVÉS DE D-ALDOHEXOSES C-6 PHOSPHORYLÉES
  申请人：LIBRAGEN

  公开号：WO2008142155A2

  公开（公告）日：2008-11-27

  [EN] The present invention concerns a method for preparing C-6 phosphorylated D- aldohexoses and C-6 phosphorylated D-aldohexose derivatives, new C-6 phosphorylated D-aldohexoses derivatives and uses thereof. The method comprises incubating polyphosphate as sole source of phosphate donor and a polyphosphate-glucose phosphotransferase (polyphosphate: D-glucose 6-phosphotransferase, EC 2.7.1.63) in an aqueous solution with aD-aldohexose or a D-aldohexose derivative.
  [FR] L'invention porte sur un procédé de préparation de D-aldohexoses C-6 phosphorylées et de dérivés de D-aldohexoses C-6 phosphorylées, sur de nouveaux dérivés de D-aldohexoses C-6 phosphorylées et sur des utilisations de ces derniers. Le procédé de l'invention consiste à faire incuber un polyphosphate, comme source unique de donneurs de phosphate, et une polyphosphate-glucose phosphotransférase (polyphosphate: D-glucose 6-phosphotransférase, EC 2.7.1.63) dans une solution aqueuse avec une D-aldohexose ou un dérivé de D-aldohexose.
• Automated Polysaccharide Synthesis: Assembly of a 30mer Mannoside
  作者：Oliviana Calin、Steffen Eller、Peter H. Seeberger

  DOI：10.1002/anie.201210176

  日期：2013.5.27

  Automated carbohydrate synthesis breaks new grounds: The longest sugar chemically synthesized to date (a 30 mer) has been accessed. Key to the process is the use of a catch–release technique, which labels the saccharide, thus allowing it to be separated later through temporary attachement to magnetic particles.

  自动化的碳水化合物合成开辟了新天地：迄今为止，化学合成最长的糖（30 mer）已经获得。该过程的关键是使用释放释放技术，该技术可以标记糖，从而可以通过暂时附着在磁性颗粒上而将其分离。
• Development of αGlcN(1↔1)αMan-Based Lipid A Mimetics as a Novel Class of Potent Toll-like Receptor 4 Agonists
  作者：Florian Adanitsch、Simon Ittig、Johannes Stöckl、Alja Oblak、Mira Haegman、Roman Jerala、Rudi Beyaert、Paul Kosma、Alla Zamyatina

  DOI：10.1021/jm500946r

  日期：2014.10.9

  The endotoxic portion of lipopolysaccharide (LPS), a glycophospholipid Lipid A, initiates the activation of the Toll-like Receptor 4 (TLR4)myeloid differentiation factor 2 (MD-2) complex, which results in pro-inflammatory immune signaling. To unveil the structural requirements for TLR4 center dot MD-2-specific ligands, we have developed conformationally restricted Lipid A mimetics wherein the flexible beta GlcN(1 -> 6)GlcN backbone of Lipid A is exchanged for a rigid trehalose-like alpha GlcN(1 <-> 1)alpha Man scaffold resembling the molecular shape of TLR4 center dot MD-2-bound E. coli Lipid A disclosed in the X-ray structure. A convergent synthetic route toward orthogonally protected alpha GlcN(1 <-> 1)alpha Man disaccharide has been elaborated. The alpha,alpha-(1 <-> 1) linkage was attained by the glycosylation of 2-N-carbamate-protected alpha-GlcN-lactol with N-phenyl-trifluoroacetimidate of 2-O-methylated mannose. Regioselective acylation with (R)-3-acyloxyacyl fatty acids and successive phosphorylation followed by global deprotection afforded bis- and monophosphorylated hexaacylated Lipid A mimetics. alpha GlcN(1 <-> 1)alpha Man-based Lipid A mimetics (alpha,alpha-GM-LAM) induced potent activation of NF-kappa B signaling in hTLR4/hMD-2/CD14-transfected HEK293 cells and robust LPS-like cytokines expression in macrophages and dendritic cells. Thus, restricting the conformational flexibility of Lipid A by fixing the molecular shape of its carbohydrate backbone in the agonistic conformation attained by a rigid alpha GlcN(1 <-> 1)alpha Man scaffold represents an efficient approach toward powerful and adjustable TLR4 activation.