methyl 2,3,4-tri-O-acetyl-6-O-tert-butyldimethylsilyl-α-D-glucopyranoside | 63734-11-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-acetyl-6-O-tert-butyldimethylsilyl-α-D-glucopyranoside
• 英文别名: Methyl 2,3,4-tri-O-acetyl-6-O-tert-butyldimethylsilyl-A-D-glucopyranoside；[(2R,3R,4S,5R,6S)-4,5-diacetyloxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-6-methoxyoxan-3-yl] acetate
• CAS: 63734-11-2
• 化学式: C₁₉H₃₄O₉Si
• 分子量: 434.559
• InChiKey: DZCGETIINZOISC-SFFUCWETSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.17
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-acetyl-6-O-tert-butyldimethylsilyl-α-D-glucopyranoside 以 乙醚 、 甲苯 为溶剂， 反应 13.0h， 生成 methyl 2,3,4-tri-O-acetyl-6-O-((E)-2-methoxycarbonylvinyl)-α-D-glucopyranoside
  参考文献：
  名称：

  A Facile, One‐Step Conversion of 6‐O‐Trityl and 6‐O‐TBDMS Monosaccharides into the Corresponding Formate Esters

  摘要：

  A convenient method has been developed for a facile and high-yield conversion of 6-O-tertbutyldimethylsilyl and 6-O-trityl protected monosaccharides to their formate esters, which may serve as useful intermediates for the replacement of the primary hydroxyl group of sugars by other functional groups.

  DOI：

  10.1080/07328300600859668
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 吡啶 作用下， 反应 24.0h， 生成 methyl 2,3,4-tri-O-acetyl-6-O-tert-butyldimethylsilyl-α-D-glucopyranoside
  参考文献：
  名称：

  A Facile, One‐Step Conversion of 6‐O‐Trityl and 6‐O‐TBDMS Monosaccharides into the Corresponding Formate Esters

  摘要：

  A convenient method has been developed for a facile and high-yield conversion of 6-O-tertbutyldimethylsilyl and 6-O-trityl protected monosaccharides to their formate esters, which may serve as useful intermediates for the replacement of the primary hydroxyl group of sugars by other functional groups.

  DOI：

  10.1080/07328300600859668

文献信息

• Amide/Iminium Zwitterionic Catalysts for (Trans)esterification: Application in Biodiesel Synthesis
  作者：Ying-Pong Lam、Xinyan Wang、Fei Tan、Wing-Hin Ng、Ying-Lung Steve Tse、Ying-Yeung Yeung

  DOI：10.1021/acscatal.9b01959

  日期：2019.9.6

  organocatalysts based on an amide anion/iminium cation charge pair has been developed. The zwitterions are easily prepared by reacting aziridines with aminopyridines. They are catalytically applicable to transesterifications and dehydrative esterifications. Mechanistic studies reveal that the amide anion and iminium cation work synergistically in activating the reaction partners, with the iminium cationic

  已经开发了一类基于酰胺阴离子/亚胺阳离子电荷对的两性离子有机催化剂。两性离子易于通过使氮丙啶与氨基吡啶反应来制备。它们催化地适用于酯交换和脱水酯化。机理研究表明，酰胺阴离子和亚胺阳离子在活化反应伙伴方面具有协同作用，亚胺阳离子部分通过非经典氢键与羰基底物相互作用。该反应可在温和条件下用于大规模合成生物柴油。
• Discriminating non-ylidic carbon-sulfur bond cleavages of sulfonium ylides for alkylation and arylation reactions
  作者：Jing Fang、Ting Li、Xiang Ma、Jiuchang Sun、Lei Cai、Qi Chen、Zhiwen Liao、Lingkui Meng、Jing Zeng、Qian Wan

  DOI：10.1016/j.cclet.2021.06.069

  日期：2022.1

  The disparate reaction pattern allowed the separate activation of non-ylidic S-alkyl and S-aryl bond. Under acidic conditions, sulfonium ylides serve as alkyl cation precursors which facilitate the alkylations. While under alkaline conditions, cleavage of non-ylidic S-aryl bond produces O-arylated compounds efficiently. The robustness of the protocols were established by the excellent compatibility of

  描述了一种在无过渡金属条件下参与烷基化和芳基化的锍叶立德。不同的反应模式允许单独激活非叶立基S-烷基和S-芳基键。在酸性条件下，锍叶立德用作促进烷基化的烷基阳离子前体。而在碱性条件下，非叶立基 S-芳基键的断裂可有效地产生O-芳基化化合物。协议的稳健性是由包括碳水化合物在内的各种底物的出色兼容性建立的。
• ZWITTERIONIC CATALYSTS FOR (TRANS)ESTERIFICATION: APPLICATION IN FLUOROINDOLE-DERIVATIVES AND BIODIESEL SYNTHESIS
  申请人：The Chinese University of Hong Kong

  公开号：US20210023539A1

  公开（公告）日：2021-01-28

  An amide/iminium zwitterion catalyst has a catalyst pocket size that promotes transesterification and dehydrative esterification. The amide/iminium zwitterions are easily prepared by reacting aziridines with aminopyridines. The reaction can be applied a wide variety of esterification processes including the large-scale synthesis of biodiesel. The amide/iminium zwitterions allow the avoidance of strongly basic or acidic condition and avoidance of metal contamination in the products. Reactions are carried out at ambient or only modestly elevated temperatures. The amide/iminium zwitterion catalyst is easily recycled and reactions proceed in high to quantitative yields.

  一种酰胺/亚胺兹维特离子催化剂具有促进酯交换和脱水酯化的催化剂口袋尺寸。酰胺/亚胺兹维特离子通过将环氮烷与氨基吡啶反应而容易制备。该反应可应用于各种酯化过程，包括生物柴油的大规模合成。酰胺/亚胺兹维特离子可避免强碱性或酸性条件，并避免产品中的金属污染。反应在常温或仅略微升温下进行。酰胺/亚胺兹维特离子催化剂易于回收，反应产率高且接近定量。
• Efficient Acetylation of Carbohydrates Promoted by Imidazole
  作者：Pallavi Tiwari、Rishi Kumar、Prakas R. Maulik、Anup Kumar Misra

  DOI：10.1002/ejoc.200500555

  日期：2005.10

  An efficient per-O-acetylation of carbohydrate derivatives and unprotected reducing sugars promoted by imidazole is reported. The reaction conditions have been successfully employed to acetylate carbohydrate derivatives containing acid-susceptible functional groups. In most of the cases the yields obtained were excellent. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

  据报道，由咪唑促进的碳水化合物衍生物和未受保护的还原糖的有效过-O-乙酰化。该反应条件已成功用于乙酰化含有酸敏感官能团的碳水化合物衍生物。在大多数情况下，获得的产率非常好。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• Fe2(SO4)3·xH2O-catalyzed per-O-acetylation of sugars compatible with acid-labile protecting groups adopted in carbohydrate chemistry
  作者：Lei Shi、Guisheng Zhang、Feng Pan

  DOI：10.1016/j.tet.2008.01.027

  日期：2008.3

  Fully acetylated saccharides are inexpensive and very useful starting materials for the synthesis of many naturally occurring glycosides, oligosaccharides, and glycoconjugates. Ferric sulfate hydrate (Fe2(SO4)3·xH2O) was found to be a valuable Lewis acid promoter in the per-O-acetylation reaction of saccharides with acetic anhydride in 100% of conversion rate and 88–99% yields. Interestingly, the procedure

  完全乙酰化的糖是便宜的，并且是用于合成许多天然存在的糖苷，寡糖和糖缀合物的非常有用的起始原料。硫酸铁水合物（铁2（SO 4）3 · X ^ h 2 O）被发现是在per-一个有价值的路易斯酸助ö糖与乙酸酐的乙酰化反应，转化率100％，产率88-99％。有趣的是，该方法与多种酸不稳定的保护基团（例如异亚丙基，亚苄基，三苯甲基和TBDMS基团）的存在完全兼容。在室温下，在2.0 mol％Fe 2（SO 4）3 · x H 2 O存在下，通过搅拌糖与少量过量的乙酸酐的混合物来简单地进行反应，并通过简单稀释即可获得纯产物。将反应混合物与二氯甲烷混合，并用Na 2 CO 3水溶液洗涤。