4-S-β-D-xylopyranosyl-4-thio-α-D-xylopyranose | 98495-94-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-S-β-D-xylopyranosyl-4-thio-α-D-xylopyranose
• 英文别名: 4-S-β-D-xylopyranosyl-4-thio-D-xylopyranose；(2S,3R,4S,5R)-2-[(3R,4R,5R,6S)-4,5,6-trihydroxyoxan-3-yl]sulfanyloxane-3,4,5-triol
• CAS: 98495-94-4
• 化学式: C₁₀H₁₈O₈S
• 分子量: 298.314
• InChiKey: YBURSWRJQHXJPD-NGIDVMRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  139.84
• 氢给体数：
  6.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  1,2,3-tri-O-benzoyl-4-O-trifluoromethylsulfonyl-β-L-arabinopyranose 在 sodium methylate 、 sodium 作用下， 以 甲醇 为溶剂， 反应 20.0h， 生成 4-S-β-D-xylopyranosyl-4-thio-α-D-xylopyranose
  参考文献：
  名称：

  不可代谢的诱导剂诱导木霉木霉中的d-木聚糖降解酶。4-硫代木糖的合成

  摘要：

  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。

  DOI：

  10.1016/0008-6215(85)90013-8

文献信息

• 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.