1,2,3-tri-O-benzoyl-4-S-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-4-thio-α-D-xylopyranose | 82040-50-4

• 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: 1,2,3-tri-O-benzoyl-4-S-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-4-thio-α-D-xylopyranose
• 英文别名: [(2R,3R,4R,5R)-2,3-dibenzoyloxy-5-[(2S,3R,4S,5R)-3,4,5-triacetyloxyoxan-2-yl]sulfanyloxan-4-yl] benzoate
• CAS: 82040-50-4
• 化学式: C₃₇H₃₆O₁₄S
• 分子量: 736.75
• InChiKey: BRWHVBIPKBKNGY-AMJVUMPOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  52
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  202
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  1,2,3-tri-O-benzoyl-4-S-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-4-thio-α-D-xylopyranose 在 氢溴酸 、 sodium methylate 、 溶剂黄146 、 三乙胺 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 1.5h， 生成 (2S,3R,4S,5R)-2-[(3R,4R,5R,6S)-6-[(3R,4R,5R,6S)-4,5-dihydroxy-6-methoxyoxan-3-yl]sulfanyl-4,5-dihydroxyoxan-3-yl]sulfanyloxane-3,4,5-triol
  参考文献：
  名称：

  Stereoselective synthesis of thioxylooligosaccharides from S-glycosyl isothiourea precursors

  摘要：

  A stereoselective synthesis of thioxylo-di-, -tri-, -tetra- and -penta-saccharides from S-glycosyl isothiourea precursors is described. The synthesis was performed starting from 2,3,4-tri-O-acetyl-beta -D-xylopyranosyl isothiouronium bromide using a triethylamine promoted reaction with 1,2,3-tri-O-benzoyl-4-O-lrifluoromethanesuIphonyl-beta -L-arabinopyranose. The resulting 4-thioxylobisse was then converted into the corresponding isothiouroniurn bromide and used for the synthesis of 4,4 ' -dithioxylotriose. Higher homologues of the series and their alpha -methyl glycosides were also prepared. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00775-4
• 作为产物：
  描述：

  2,3,4-三-O-乙酰基-α-D-木吡喃糖苷溴 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 60.25h， 生成 1,2,3-tri-O-benzoyl-4-S-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-4-thio-α-D-xylopyranose
  参考文献：
  名称：

  Stereoselective synthesis of thioxylooligosaccharides from S-glycosyl isothiourea precursors

  摘要：

  A stereoselective synthesis of thioxylo-di-, -tri-, -tetra- and -penta-saccharides from S-glycosyl isothiourea precursors is described. The synthesis was performed starting from 2,3,4-tri-O-acetyl-beta -D-xylopyranosyl isothiouronium bromide using a triethylamine promoted reaction with 1,2,3-tri-O-benzoyl-4-O-lrifluoromethanesuIphonyl-beta -L-arabinopyranose. The resulting 4-thioxylobisse was then converted into the corresponding isothiouroniurn bromide and used for the synthesis of 4,4 ' -dithioxylotriose. Higher homologues of the series and their alpha -methyl glycosides were also prepared. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00775-4

文献信息

• Aryl 4-thioxylobioside and 1,4-dithioxylobiosides as effectors of the enzymic activity for fungal d-xylanases
  作者：Jean Comtat、Jacques Defaye、Hugues Driguez、Eric Ohleyer

  DOI：10.1016/0008-6215(85)85004-7

  日期：1985.11

  hydrolysis by xylanase which may involve extracellular regulation by small oligosaccharides. The aminodithiodisaccharide 10 was coupled to CH-Sepharose 4B to give an affinity gel which retained xylanase activities.

  摘要在碳酸钾存在下，丙酮中五邻O-酰基-4-硫代-β-木糖基溴与邻硝基苯酚，对硝基苯硫醇或对氨基苯硫醇的反应，然后进行邻O脱酰反应，得到了优异的结果。得到邻硝基苯基4-硫代-β-木糖苷（8），对硝基苯基和对氨基苯基的1，4-二硫代-β-木糖苷（10）。化合物8表现为来自二孢子孢菌的木聚糖酶A和B的良好发色底物，K m分别为2.4和6m m。10的N-乙酰基衍生物以及游离的二糖4-巯基木糖是木聚糖酶B的竞争性抑制剂（K i分别为2.5和0.72mm），但在培养时显着提高了木聚糖酶A对d-木聚糖的水解速度。与该基板同时进行（KA分别为0.19和0.18mm）；合成底物8的水解速率在类似条件下不受影响。这些结果表明了木聚糖酶对d-木聚糖水解的调节机制的可能性，该机制可能涉及小的寡糖的细胞外调节。将氨基二硫代二糖10与CH-Sepharose 4B偶联，得到保留木聚糖酶活性的亲和凝胶。
• Induction of d-xylan-degrading enzymes in Trichoderma lignorum by nonmetabolizable inducers. A synthesis of 4-thioxylobiose
  作者：Jacques Defaye、Hugues Driguez、Michael John、Jürgen Schmidt、Eric Ohleyer

  DOI：10.1016/0008-6215(85)90013-8

  日期：1985.6

  The d -xylan-degrading enzymes of Trichoderma lignorum can be induced by several oligo- and poly-saccharides. The induction is optimal when l -arabino- d -xylan is used as carbon source. The enzymes were also produced by cells grown on glycerol in the presence of 4-thioxylobiose (4- S -β- d -xylopyranosyl-4-thio- d -xylopyranose) and methyl β- d -xylopyranoside. These inducers were not taken up by the

  摘要木糖木霉的d-木聚糖降解酶可以被多种寡糖和多糖诱导。当1-阿拉伯-d-木聚糖用作碳源时，诱导是最佳的。该酶也是由在4-硫代木糖（4-S-β-d-木吡喃糖基-4-硫代-d-木吡喃糖）和甲基β-d-木吡喃糖苷存在下在甘油上生长的细胞产生的。这些诱导物未被细胞吸收。然而，诱导程度低于木二糖。1,2,3-三-O-苯甲酰基-4-O-三氟甲基磺酰基-β-1-阿糖基吡喃糖与1-硫代-β-钠盐的反应得到硫代叶酰糖，总产率为55-60％。在N′，N″，N′-六甲基磷酰胺中的d-吡喃木糖，然后将所得的4-硫代二糖进行O-脱酰。
• Positional isomers of thioxylobiose, their synthesis and inducing ability for d-xylan-degrading enzymes in the yeast cryptococcus albidus
  作者：Jacques Defaye、Jean-Michel Guillot、Peter Biely、Mária Vršanská

  DOI：10.1016/s0008-6215(00)90548-2

  日期：1992.4

  Isomeric S-linked 2-thioxylobiose 10, 3-thioxylobiose 17, and 4-thioxylobiose 19 were conveniently prepared by SN2 displacement of suitable triflylglycoses with the sodium salt of 2,3,4-tri-O-acetyl-1-thio-beta-D-glucopyranose, either in N,N-dimethylformamide, or in oxolan in the presence of a sodium complexing agent. Allyl 3,5-O-isopropylidene-2-O-trifluoromethanesulfonyl-beta-D-lyxofuranoside was a convenient electrophilic precursor for 10, which was smoothly obtained after a short sequence of deprotection involving conversion to the 1-propenyl glycoside. 1,2:5,6-Di-O-isopropylidene-3-O-trifluoromethylsulfonyl-alpha-D-allofuranose and 1,2,3-tri-O-benzoyl-4-O-trifluoromethylsulfonyl-beta-L-arabinopyranose were the respective precursors for 17 and 19. 4-Thioxylobiose has a highly stimulatory effect on the synthesis of enzymes of the xylanolytic system in the yeast Cryptococcus albidus when applied to the cells in the presence of the natural disaccharide inducer (1 --> 4)-beta-D-xylobiose.