methyl 2,3-di-O-acetyl-6-O-benzoyl-α-D-glucopyranoside | 29868-43-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-di-O-acetyl-6-O-benzoyl-α-D-glucopyranoside
• 英文别名: methyl-(O²,O³-diacetyl-O⁶-benzoyl-α-D-glucopyranoside)；Methyl-(O²,O³-diacetyl-O⁶-benzoyl-α-D-glucopyranosid)；I+/--D-Glucopyranoside, methyl, 2,3-diacetate 6-benzoate；[(2R,3R,4S,5R,6S)-4,5-diacetyloxy-3-hydroxy-6-methoxyoxan-2-yl]methyl benzoate
• CAS: 29868-43-7
• 化学式: C₁₈H₂₂O₉
• 分子量: 382.367
• InChiKey: CNGAZEBWIIDYHF-QFXBJFAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  methyl-4,6-O-benzylidene-2,3-diacetyl-α-D-glucopyranoside 生成 methyl 2,3-di-O-acetyl-6-O-benzoyl-α-D-glucopyranoside
  参考文献：
  名称：

  SATO, KEN-ICHI;JGARASHI, TETSUTARO;YANAGISAWA, YUKIO;KAWAUCHI, NOBUYA;HAS+, CHEM. LETT.,(1988) N 10, C. 1699-1702

  摘要：

  DOI：

文献信息

• Acylation of carbohydrates over Al2O3: preparation of partially and fully acylated carbohydrate derivatives and acetylated glycosyl chlorides
  作者：Pallavi Tiwari、Anup Kumar Misra

  DOI：10.1016/j.carres.2005.11.035

  日期：2006.2

  protocol does not require the addition of any base or activator. This methodology has been further extended to the selective acylation of carbohydrate diols and the one-pot preparation of acetylated glycosyl chlorides direct from free reducing sugars. The yields obtained in most of the cases are excellent.

  据报道，使用酰氯和固体支持剂Al2O3对碳水化合物衍生物进行选择性和全O酰化。该协议不需要添加任何碱或活化剂。该方法已经进一步扩展到碳水化合物二醇的选择性酰化和直接从游离还原糖直接制备一锅乙酰化糖基氯的方法。在大多数情况下所获得的产量是极好的。
• Facile cleavage of carbohydrate benzyl ethers and benzylidene acetals using the reagent under two-phase conditions
  作者：Matteo Adinolfi、Gaspare Barone、Luigi Guariniello、Alfonso Iadonisi

  DOI：10.1016/s0040-4039(99)01756-6

  日期：1999.11

  benzylidene acetal carbohydrate protecting groups can be selectively cleaved by reaction with sodium bromate/sodium dithionite in ethyl acetate/water. Under the mild (room temperature, short reaction time) conditions needed, a variety of other protecting functionalities such as acetyl, chloroacetyl, benzoyl, pivaloyl, tosyl, t-butyldimethylsilyl, trityl, and isopropylidene groups remain unaffected.

  苄基醚和亚苄基缩醛碳水化合物保护基团可以通过与溴酸钠/连二亚硫酸钠在乙酸乙酯/水中反应选择性地裂解。在所需的温和（室温，短反应时间）条件下，各种其他保护功能如乙酰基，氯乙酰基，苯甲酰基，新戊酰基，甲苯磺酰基，叔丁基二甲基甲硅烷基，三苯甲基和异亚丙基仍不受影响。
• Glycosylated Eumelanin Building Blocks by Thioglycosylation of 5,6-Diacetoxyindole with an Expedient Selenium-Based Dynamic-Mixture Methodology
  作者：Matteo Adinolfi、Marco d'Ischia、Alfonso Iadonisi、Loredana Leone、Alessandro Pezzella、Silvia Valerio

  DOI：10.1002/ejoc.201200299

  日期：2012.8

  A series of 3-thioglycosylated 5,6-diacetoxyindole derivatives, which are important tools for eumelanin research and application, were prepared through a practical and efficient approach exploiting a dynamic mixture of thioglycoside agents. The strategy is feasible for installing both mono- and disaccharide units and relies on the facile in situ conversion of glycosyl disulfides into the corresponding

  一系列 3-硫糖基化 5,6-二乙酰氧基吲哚衍生物是真黑素研究和应用的重要工具，通过利用硫糖苷试剂的动态混合物的实用和有效的方法制备。该策略对于安装单糖和二糖单元都是可行的，并且依赖于在二苯基二硒化物、N-溴代琥珀酰亚胺 (NBS) 和四丁基溴化铵 (TBAB) 存在下，糖基二硫化物易于原位转化为相应的、更具反应性的苯基硫化物）。
• Regioselective oxidative cleavage of benzylidene acetals: synthesis of highly functionalized chiral intermediates
  作者：Pon Minor Senthilkumar、Appu Aravind、Sundarababu Baskaran

  DOI：10.1016/j.tetlet.2006.12.078

  日期：2007.2

  A mild and efficient method for the regioselective oxidative cleavage of benzylidene acetals with KBrO3/Na2S2O4 under bi-phasic conditions (EtOAc/H2O), leading to highly functionalized chiral intermediates, is reported.

  报道了在两相条件下（EtOAc / H 2 O）用KBrO 3 / Na 2 S 2 O 4进行亚苄基乙缩醛的区域选择性氧化裂解的温和有效方法，导致高度官能化的手性中间体。
• Oxidative Cleavage of 4,6-<i>O</i>-Benzylidene Ring with t-Butyl Hydroperoxide and Copper(II) Chloride. Preparation of Methyl 4-<i>O</i>- and 6-<i>O</i>-Benzoylhexopyranoside Derivatives
  作者：Ken-ichi Sato、Tetsutaro Igarashi、Yukio Yanagisawa、Nobuya Kawauchi、Hironobu Hashimoto、Juji Yoshimura

  DOI：10.1246/cl.1988.1699

  日期：1988.10.5

  Copper(II) chloride and palladium(II) acetate were found to be highly effective catalysts for oxidative cleavage of O-benzylidene ring with t-butyl hydroperoxide. Using the former catalyst 4,6-O-benzylidenehexopyranoside derivatives were converted into the corresponding 4- and 6-benzoates in high yields. This reaction was also applicable for conversion of benzyl group into benzoyl one.

  发现氯化铜 (II) 和乙酸钯 (II) 是使用叔丁基氢过氧化物氧化裂解 O-亚苄基环的高效催化剂。使用前一种催化剂，4,6-O-亚苄基己基吡喃糖苷衍生物以高产率转化为相应的4-和6-苯甲酸酯。该反应也适用于将苄基转化为苯甲酰基。