6-O-(p-toluenesulfonyl)sucrose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-(p-toluenesulfonyl)sucrose
• 英文别名: 6-O-toluolsulfonyl-D-glucopyranosyl-beta-D-fructofuranoside；Tos(-6)Glc(a1-2b)Fruf；[(2R,3S,4S,5R,6R)-6-[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl 4-methylbenzenesulfonate
• 化学式: C₁₉H₂₈O₁₃S
• 分子量: 496.49
• InChiKey: LGAGORYAYVRUIR-ZSOARRGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  221
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  6-O-(p-toluenesulfonyl)sucrose 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 生成 β-D-fructofuranosyl 6-azido-6-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  [EN] A NEW CLASS OF SUCROSE ESTERS AND A METHOD FOR THEIR PREPARATION
  [FR] NOUVELLE CLASSE D'ESTERS DE SACCHAROSE ET PROCÉDÉ DE PRÉPARATION CORRESPONDANT

  摘要：

  本发明涉及一种新型蔗糖酯类化合物及其制备方法。

  公开号：

  WO2019043069A1
• 作为产物：
  描述：

  6-O-toluolsulfonyl-D-glucopyranose 、 蔗糖 在 Bacillus megaterium (SacB) 作用下， 以 aq. buffer 为溶剂， 反应 1.0h， 生成 6-O-(p-toluenesulfonyl)sucrose
  参考文献：
  名称：

  [EN] A NEW CLASS OF SUCROSE ESTERS AND A METHOD FOR THEIR PREPARATION
  [FR] NOUVELLE CLASSE D'ESTERS DE SACCHAROSE ET PROCÉDÉ DE PRÉPARATION CORRESPONDANT

  摘要：

  本发明涉及一种新型蔗糖酯类化合物及其制备方法。

  公开号：

  WO2019043069A1

文献信息

• Library of mild and economic protocols for the selective derivatization of sucrose under microwave irradiation
  作者：M. Teresa Barros、Krasimira T. Petrova、Paula Correia-da-Silva、Taterao M. Potewar

  DOI：10.1039/c1gc15228a

  日期：——

  The chemistry of sucrose is very challenging due to its eight hydroxyl groups, three of which are primary, with very similar reactivities, thus control of the chemoselectivity is a central issue. In this work, the selective formation of monounsaturated esters at the 6-position, by applying the Mitsunobu conditions for the selective esterification of sucrose, is reported. Also, the outcome of a number of mono-substitution reactions at positions 6 or 6′, and di-substitution reactions at positions 6 and 6′ have been explored. Mild and energy-efficient procedures, with short reaction times (5 to 10 min) using microwave irradiation have been developed, and the results compared with conventional procedures. In some cases, the use of microwave irradiation appeared to provide not only time saving but also improved selectivity.

  蔗糖的化学性质非常具有挑战性，因为它有八个羟基，其中三个是伯羟基，具有非常相似的反应活性，因此化学选择性的控制是一个中心问题。在这项工作中，报道了通过应用蔗糖选择性酯化的 Mitsunobu 条件，在 6 位选择性形成单不饱和酯。此外，还探讨了位置 6 或 6' 处的许多单取代反应以及位置 6 和 6' 处的双取代反应的结果。已经开发出使用微波辐射的温和且节能的程序，反应时间短（5至10分钟），并将结果与​​传统程序进行了比较。在某些情况下，使用微波辐射似乎不仅可以节省时间，还可以提高选择性。
• Direct regioselective 2-O-(p-toluenesulfonylation) of sucrose
  作者：Katsunori Teranishi

  DOI：10.1016/s0008-6215(02)00039-3

  日期：2002.4

  2-O-(p-Toluenesulfonyl)sucrose was regioselectively synthesized by direct p-toluenesulfonylation of sucrose using N-(p-toluenesulfonyl)imidazole in the presence of molecular sieves at 40degreesC. The reactivities of the sucrose hydroxy groups toward this sulfonylation increased in the order as follows: OH-2 much greater than OH-1' > OH-3' > OH-6 > OH-6'. These results were diametrically opposite to the expected sulfonylation with p-toluenesulfonyl chloride in pyridine. for which the reactivity increased in the order as follows: OH-6', OH-6 much greater than OH-1' > OH-2. The desired 2-O-(p-toluenesulfonyl)sucrose was readily isolated by simple open reversed-phase column chromatography. followed by recrystallization, thus overcoming the main difficulties associated with regioselectivity, efficiency, and isolation techniques for the practical preparation. (C) 2002 Elsevier Science Ltd. All rights reserved.
• [EN] A NEW CLASS OF SUCROSE ESTERS AND A METHOD FOR THEIR PREPARATION<br/>[FR] NOUVELLE CLASSE D'ESTERS DE SACCHAROSE ET PROCÉDÉ DE PRÉPARATION CORRESPONDANT
  申请人：UNIV WUERZBURG J MAXIMILIANS

  公开号：WO2019043069A1

  公开（公告）日：2019-03-07

  The present invention relates to a new class of sucrose esters and a method for their preparation.

  本发明涉及一种新型蔗糖酯类化合物及其制备方法。