methyl 3,6-di-O-benzoyl-α-D-glucopyranoside | 80245-05-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,6-di-O-benzoyl-α-D-glucopyranoside
• 英文别名: Methyl-3,6-di-O-benzoyl-α-D-glucopyranosid；[(2R,3R,4S,5R,6S)-4-benzoyloxy-3,5-dihydroxy-6-methoxyoxan-2-yl]methyl benzoate
• CAS: 80245-05-2
• 化学式: C₂₁H₂₂O₈
• 分子量: 402.401
• InChiKey: WCYRUJGIOQEIFC-NLJKLAEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  methyl 3, 6-di-O-benzoyl-α-D-mannopyranoside 在 硼氘化钠 、 4 A molecular sieve 、 sodium acetate 、 pyridinium chlorochromate 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 61.0h， 生成 methyl 3,6-di-O-benzoyl-α-D-glucopyranoside
  参考文献：
  名称：

  Klausener, Alexander; Runsink, Jan; Scharf, Hans-Dieter, Liebigs Annalen der Chemie, 1984, # 4, p. 783 - 790

  摘要：

  DOI：

文献信息

• Regioselective O-deacylation of fully acylated glycosides and 1,2-O-isopropylidenealdofuranose derivatives with hydrazine hydrate
  作者：Hoshiharu Ishido、Nobuo Sakairi、Masao Sekiya、Nobuo Nakazaki

  DOI：10.1016/s0008-6215(00)80525-x

  日期：1981.11

  partial O -deacylation of fully acylated methyl glycosides and some other glycosyl compounds (23 compounds) was found to be induced, to give, in good yields, products bearing one free hydroxyl group; the results obtained indicated that, among the primary and secondary O -acyl groups, the 2- O -acyl groups were, in general, the most labile toward the nucleophile (hydrazine). Hydrazinolysis of 1,2- O -

  摘要在1：4乙酸-吡啶中进行肼解后，在吡啶中，可诱导完全酰化的甲基糖苷和某些其他糖基化合物（23种化合物）的部分O-脱酰作用，从而以较高的收率得到含1种化合物的产物。游离羟基 所得结果表明，在伯和仲O-酰基中，2-O-酰基通常对亲核试剂（肼）最不稳定。另一方面，对1，2-O-异亚丙基戊二醛呋喃糖酰化物（3种化合物）进行水合肼解，以高收率得到相应的在其伯羟基上具有保护基的单酰基衍生物。讨论了可能与肼解的区域选择性有关的因素。
• Facile oxidative cleavage of benzylidene acetals using molecular oxygen catalyzed by N -hydroxyphthalimide/Co(OAc) 2
  作者：Yongsheng Chen、Peng George Wang

  DOI：10.1016/s0040-4039(01)00905-4

  日期：2001.7

  Benzylidene acetals derived from 1,2- and 1,3-diols undergo facile oxidative cleavage to give hydroxy benzoate esters with molecular oxygen in the presence of catalytic amount of N-hydroxyphthalimide/Co(OAc)2.

  在催化量的N-羟基邻苯二甲酰亚胺/ Co（OAc）2存在下，衍生自1,2-和1,3-二醇的亚苄基缩醛容易进行氧化裂解，从而与分子氧一起生成羟基苯甲酸酯。
• From methyl d-glucopyranoside to methyl d-allopyranoside via the Mitsunobu reaction
  作者：Mikhail Kim、Barbara Grzeszczyk、Aleksander Zamojski

  DOI：10.1016/s0008-6215(99)00160-3

  日期：1999.8

  Methyl β-d-glucopyranoside reacted with a 4-molar excess of the Mitsunobu reagents (triphenylphosphine–diethyl azodicarboxylate–benzoic acid) under Weinges et al. [Carbohydr. Res., 164 (1987) 453–458] conditions to furnish four differently benzoylated methyl β-d-allopyranosides in a very good overall yield. The same reaction applied to methyl α-d-glucopyranoside yielded allosides in a low yield and

  在Weinges等人的研究中，甲基β-d-吡喃葡萄糖苷与4摩尔过量的Mitsunobu试剂（三苯基膦-偶氮二羧酸二乙酯-苯甲酸）反应。[碳水化合物。Res。，164（1987）453–458]条件提供了四种不同的苯甲酰化的甲基β-d-吡喃果糖苷，总收率非常好。应用于甲基α-d-吡喃葡萄糖苷的相同反应以低收率产生了同素苷，并产生了其他九种糖产品。这些结果使我们深入了解了Mitsunobu酯化-转化反应的过程。
• A green and convenient method for regioselective mono and multiple benzoylation of diols and polyols
  作者：Xiaoling Zhang、Bo Ren、Jiantao Ge、Zhichao Pei、Hai Dong

  DOI：10.1016/j.tet.2015.12.074

  日期：2016.2

  An efficient method for regioselective benzoylation of diols and polyols was developed. The benzoylation is catalyzed by only 0.2 equiv of benzoate anion in acetonitrile with the addition of a stoichiometric amount of benzoic anhydride under very mild condition, leading to high yields. Compared with all other methods, this method shows particular advantage in regioselective multiple benzoylation of polyols, and in avoiding the use of any metal-based catalysts and any amine bases, which is more environment friendly. (C) 2015 Elsevier Ltd. All rights reserved.