1,2,3,2',3',4'-hexa-O-acetyl-α-xylobiose | 73719-69-4

• 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: 1,2,3,2',3',4'-hexa-O-acetyl-α-xylobiose
• 英文别名: acetyl 2,3,4-tri-O-acetyl-β-D-xylopyranosyl-(1→4)-2,3-di-O-acetyl-α-D-xylopyranoside
• CAS: 73719-69-4
• 化学式: C₂₂H₃₀O₁₅
• 分子量: 534.471
• InChiKey: USXJUXMLGWBRHW-ZHPQPJTISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.69
• 重原子数：
  37.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  185.49
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  1,2,3,2',3',4'-hexa-O-acetyl-α-xylobiose 在 Candida antartica 作用下， 以 异丙醇 为溶剂， 生成 1,2,3,2',3'-penta-O-acetyl-α-xylobiose
  参考文献：
  名称：

  Synthesis of a library of allyl α-l-arabinofuranosyl-α- or β-d-xylopyranosides; route to higher oligomers

  摘要：

  Six isomeric disaccharides allyl 2,3,5-tri-O-benzoyl-alpha-L-arabinofuranosyl-alpha-D-xylopyranosides and beta-D-xylopyranosides were synthetized by the stereoselective glycosylation of pure allyl alpha- or beta-D-xylopyranosides with 1-O-acetyl-2,3,5-tri-O-benzoyl-L-arabinofuranose as donor, catalyzed with BF3.Et2O in DCM. Regio- and stereoselective glycosylation with excess of donor furnished almost exclusively the trisaccharides allyl 2,3-di-O-(2,3,5-tri-O-benzoyl-alpha-L-arabinofuranosyl)-alpha- or beta-D-xylopyranosides. Extension of the reaction to the triol beta-D-xylopyranosyl-(1 -> 4)-1,2,3-tri-O-acetyl-alpha-D-xylopyranose, obtained from the 4-hydroxyl penta-O-acetyl-alpha-xylobiose, gave in the same manner the tetrasaccharide [2,3-di-O-(2,3,5-tri-O-benzoyl-alpha-L-arabinofuranosyl)-beta-D-xylopyranosyl]-(1 -> 4 )-1,2,3-tri-O-acetyl-alpha-D-xylopyranose. The protocol described herein should offer the possibility to produce branched oligosaccharides with a 2,3-di-O-(alpha-L-Ara(f))-beta-D-Xyl(p) block unit at the terminal non-reducing end. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.08.007
• 作为产物：
  描述：

  D-(+)-xylobiose 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 4.0h， 以4%的产率得到
  参考文献：
  名称：

  具有定义分支模式的量身定制的多糖：阿拉伯木聚糖寡糖的酶促聚合。

  摘要：

  非纤维素多糖（如阿拉伯木聚糖）的异质性使得难以将分子结构与宏观特性相关联。为了研究多糖的特定结构特征对结晶度或对其他细胞壁成分的亲和力的影响，需要收集具有确定的重复单元的多糖。在本文中，描述了化学酶促方法来制备具有系统地改变的分支模式的人工阿拉伯木聚糖多糖。多糖是通过糖合酶催化的阿拉伯糖基木聚糖寡糖衍生的糖基氟化物聚合而获得的。纤维素表面的X射线衍射和吸附实验表明，合成多糖的理化性质强烈取决于其取代模式的特定性质。人造多糖允许进行其他方法无法访问的结构与性质之间的关系研究。

  DOI：

  10.1002/anie.201806871

文献信息

• An efficient chemical-enzymatic synthesis of 4-nitrophenyl β-xylobioside: a chromogenic substrate for xylanases
  作者：Adva Mechaly、Valery Belakhov、Yuval Shoham、Timor Baasov

  DOI：10.1016/s0008-6215(97)00209-7

  日期：1997.11

  Abstract 4-Nitrophenyl-β-xylobioside was synthesized by an improved short chemical-enzymatic method, based on the use of xylobiose as a starting material. Xylobiose was prepared following extensive enzymatic digestion of birchwood xylan with xylanase T-6. The resulting digest, containing mainly xylobiose and xylose, was directly subjected to an acetylation step, which after silica gel chromatography

  摘要以木糖为原料，采用改进的短化学酶法合成了4-硝基苯基-β-木糖苷。在用木聚糖酶T-6对桦木木聚糖进行广泛的酶消化之后，制备木糖。将所得的主要包含木糖和木糖的消化物直接进行乙酰化步骤，该步骤在硅胶色谱法后提供高纯度的木糖六乙酸盐。用乙酸中的HBr溴化可定量获得相应的溴化物，在偶联和脱保护步骤后，可得到目标物4-硝基苯基-β-木二糖苷。
• Synthesis of ginsenoside Rg3, a minor constituent of Ginseng Radix
  作者：Victor Ph. Anufriev、Galina V. Malinovskaya、Vladimir A. Denisenko、Nina I. Uvarova、Georgi B. Elyakov、Shin-Il Kim、Nam-In Baek

  DOI：10.1016/s0008-6215(97)00217-6

  日期：1997.11

  Glycosylation of 12 beta-acetoxy-dammar-24-en-3 beta,20(S)-diol (4), with hepta-O-acetyl-alpha-sophorosyl bromide (5) under catalysis by Ag2CO3 or Ag2O afforded a chromatographically unseparated mixture of the alpha-and beta-linked octaacetates 6 and 7 in an approximately 2.5:1 ratio. After deprotection and chromatographic purification, the free alpha- (8) and beta-glycosides (9) were obtained. Sophoroside 9 was identical in all respects with ginsenoside Rg(3), the minor component of Ginseng Radix rubra. All compounds were fully characterized by H-1 and C-13 NMR spectroscopy, (C) 1997 Elsevier Science Ltd. All rights reserved.