methyl 3,5-di-O-benzyl-2-O-(p-toluenesulfonyl)-D-xylofuranoside | 211557-52-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,5-di-O-benzyl-2-O-(p-toluenesulfonyl)-D-xylofuranoside
• 英文别名: 1-O-methyl 2-O-tosyl 3,5-di-O-benzyl α,β(D)xylo-pentoaldofuranose；[(3R,4S,5R)-2-methoxy-4-phenylmethoxy-5-(phenylmethoxymethyl)oxolan-3-yl] 4-methylbenzenesulfonate
• CAS: 211557-52-7
• 化学式: C₂₇H₃₀O₇S
• 分子量: 498.597
• InChiKey: NNIRLZDDMBSGJG-TXVRJSAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  88.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 3,5-di-O-benzyl-2-O-(p-toluenesulfonyl)-D-xylofuranoside 在 三氟乙酸 作用下， 以 四氢呋喃 、 水 为溶剂， 以75%的产率得到3,5-di-O-benzyl-2-O-tosyl-D-xylofuranose
  参考文献：
  名称：

  An Epoxide Derived from D-Glucose as the Key Intermediate for Penaresidine and Sphingolipids Synthesis

  摘要：

  A multigram-scale synthesis of 3R,4R,5R 3,5-dibenzyloxy-4-p-methoxybenzyl-1,2-epoxypentane and its use as intermediate for sphingolipids, penazeridine and penazetidine synthesis are described.

  DOI：

  10.1080/00397919808004296
• 作为产物：
  描述：

  3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose 在 吡啶 、 硫酸 作用下， 反应 23.0h， 生成 methyl 3,5-di-O-benzyl-2-O-(p-toluenesulfonyl)-D-xylofuranoside
  参考文献：
  名称：

  1,2-脱水-6- O-乙酰基-3,4-二-O-苄基-d-甘露糖和1,2-脱水5- O-乙酰基-3- O-苄基-D-的简便合成糖呋喃糖酶

  摘要：

  偶联碳水化合物实体以产生糖苷或更高级低聚物的能力是合成有机化学的重要目标。1在过去的几十年中，由于糖苷化方法的发展，构建糖苷键的方法得到了改善。2然而，由于其结构复杂性，与寡肽和寡核苷酸的合成相比，寡糖的合成仍然是一项艰巨的任务。需要许多其他的糖衍生物，它们可以改善和简化寡糖的合成过程。

  DOI：

  10.1080/07328309808007470

文献信息

• A Facile Synthesis of 1,2-Anhydro-6-<i>O</i>-acetyl-3,4-di-<i>O</i>-benzyl-d-glycopyranoses and 1,2-Anhydro-5-<i>O</i>-acetyl-3-<i>O</i>-benzyl-D-glycofuranoses
  作者：Jun Ning、Fanzuo Kong

  DOI：10.1080/07328309808007470

  日期：1998.8.1

  The ability to couple carbohydrate entities to produce glycosides or higher oligomers is an important goal of synthetic organic chemistry.1 For the past several decades, methods to construct glycosidic linkages have improved as a result of the development of glycosidation procedures.2 However, owing to their structural complexity, synthesis of oligosaccharides is still a laborious task compared with

  偶联碳水化合物实体以产生糖苷或更高级低聚物的能力是合成有机化学的重要目标。1在过去的几十年中，由于糖苷化方法的发展，构建糖苷键的方法得到了改善。2然而，由于其结构复杂性，与寡肽和寡核苷酸的合成相比，寡糖的合成仍然是一项艰巨的任务。需要许多其他的糖衍生物，它们可以改善和简化寡糖的合成过程。
• An Epoxide Derived from D-Glucose as the Key Intermediate for Penaresidine and Sphingolipids Synthesis
  作者：Josiane Beauhaire、Paul-Henri Ducrot

  DOI：10.1080/00397919808004296

  日期：1998.7

  A multigram-scale synthesis of 3R,4R,5R 3,5-dibenzyloxy-4-p-methoxybenzyl-1,2-epoxypentane and its use as intermediate for sphingolipids, penazeridine and penazetidine synthesis are described.
• Syntheses and reactions of 5-O-acetyl-1,2-anhydro-3-O-benzyl-α-d-ribofuranose and -β-d-lyxofuranose, 5-O-acetyl-1,2-anhydro-3,6-di-O-benzyl- and 1,2-anhydro-5,6-di-O-benzoyl-3-O-benzyl-β-d-mannofuranose, and 6-O-acetyl-1,2-anhydro-3,4-di-O-benzyl-α-d-glucopyranose and -β-d-talopyranose
  作者：Jun Ning、Fanzuo Kong

  DOI：10.1016/s0008-6215(00)00290-1

  日期：2001.1

  The title compounds 5-O-acetyl-1,2-anhydro-3-O-benzyl-alpha -D-ribofuranose and 5-O-acetyl-1,2-anhydro-3-O-benzyl-beta -D-lyxofuranose, and 6-O-acetyl-1,2-auhydro-3,4-di-O-benzyl-alpha -D-glucopyranose and 6-O-acetyl-1,2-anhydro-3,4-diO-benzyl-beta -D-taloypranose, and 5-O-acetyl-1,2-anhydro-3,6-di-O-benzyl-beta -D-mannofuranose and 1,2-anhydro-5,6-di-O-benzoyl-3-O-benzyl-beta -D-mannofuranose have each been synthesized from the corresponding 2-O-tosylate and 1-free hydroxyl inter-mediates by base-initiated intramolecular S(N)2 ring closure in almost quantitative yields. Acetyl and benzoyl groups were not affected in the ring closure reactions. Condensation of 6-O-acetyl-1,2-anhydro-3,4-di-O-benzyl-alpha -D-glucopyranose and 5-O-acetyl-1,2-anhydro-3,6-di-O-benzyl-beta -D-mannpfuranose with 1,2:3,4-di-O-isopropylidene-alpha -D-galactopyranose in the presence of ZnCl2 as the catalyst afforded the 1,2-trans-linked 6-O-acetyl-3,4-di-O-benzyl-alpha -D-glucopyranosyl-(1-6)-1,2:3,4-di-O-isopropylidene-alpha -D-galactopyranose and 5-O-acetyl-3,6-di-O-benzyl-alpha -O-mannofuranosyl-(1-->6)-1,2:3,4-di-O-isopropylidene-a-D-galactopyranose as the sole products in satisfactory yields, while condensation of 5-O-acetyl-1,2-anhydro-3-O-benzyl-beta -D-lyxofuranose with 3-O-benzyl-1,2-O-isoproyylidene-alpha -D-xylofuranose yielded the 1,2-trans-linked 5-O-acetyl-3-O-benzyl-alpha -D-lyxofuranosyl-(1-->5)-3-O-benzyl-1,3-O-isopropylidene-alpha -D-xylofuranose as the sole product in a good yield. The 6-O-acetyl group in the glycosyl donor, 6-O-acetyl-1,2-anhydro-3,4-di-O-brnzyl-alpha -D-glucopyranose did not influence the stereoselectivity of the ring-opening-coupling, reaction. (C) 2001 Published by Elsevier Science Ltd. All rights reserved.