allyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside | 202600-40-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: allyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside
• 英文别名: [(2R,4aR,6R,7R,8R,8aS)-7-(1,3-dioxoisoindol-2-yl)-2-phenyl-6-prop-2-enoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] acetate
• CAS: 202600-40-6
• 化学式: C₂₆H₂₅NO₈
• 分子量: 479.486
• InChiKey: MEKVKGOSHDKMAY-NKCSVIPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  allyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 三氯化铝 、 硼烷-三甲胺络合物 、 4 A molecular sieve 、 lithium perchlorate 、 cesium fluoride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 74.5h， 生成 Acetic acid (2R,3R,4R,5S,6R)-2-allyloxy-6-benzyloxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Synthesis of Fucosyl Saccharides under Neutral Conditions in Solutions of Lithium Perchlorate in Dichloromethane

  摘要：

  Trisaccharides embodying the Fuc-alpha-(1-2)-Gal or the Fuc-alpha-(1-2)-Glc substructure can be built up under neutral conditions by glycosylation of selectively deprotected glycosyl acceptor disaccharides with 2,3,4-tri-O-benzyl fucosyl fluoride in 0.07 M solutions of LiClO4 in CH2Cl2. The glycosyl and the galactosyl trisaccharides, which are stereoisomers of the carbohydrate determinant of the human blood group H, are obtained in high yield and with complete alpha-selectivity. The glycosyl acceptor disaccharides with a deblocked 2-OH group in the saccharide unit are obtained by treatment of the respective 1,2-anhydro carbohydrates with glycosyl acceptors in 0.07 M LiClO4/CH2Cl2.

  DOI：

  10.1002/(sici)1521-3765(19980310)4:3<494::aid-chem494>3.0.co;2-8
• 作为产物：
  描述：

  allyl 3,4,6-tri-O-acetyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside 在 吡啶 、 盐酸 、 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 生成 allyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Lamberth, Clemens; Nagy, Jon O.; Kasper, Cornelia, Journal of Carbohydrate Chemistry, 1994, vol. 13, # 5, p. 819 - 824

  摘要：

  DOI：

文献信息

• A Novel and Efficient Deprotection of the Allyl Group at the Anomeric Oxygen of Carbohydrates
  作者：Biao Yu、Jianbo Zhang、Shoufu Lu、Yongzheng Hui

  DOI：10.1055/s-1998-1579

  日期：1998.1

  Perfluoroalkylation with perfluoroalkyl iodide under sodium dithionite and sodium bicarbonate in acetonitrile/water followed by elimination in the presence of zinc powder and ammonium chloride in ethanol was disclosed to be an extremely mild and efficient procedure for deprotection of the anomeric allyl group of carbohydrates.

  在乙腈/水体系中，通过二硫酸钠和碳酸氢钠与全氟烷基碘化物进行全氟烷基化反应，随后在乙醇中以锌粉和氯化铵为条件进行消除反应，这一过程被揭示为一种极为温和且高效的去保护碳水化合物异头位烯丙基的方法。
• Synthesis and NMR analysis of model compounds related to fucosylated chondroitin sulfates: GalNAc and Fuc(1 → 6)GalNAc derivatives
  作者：Dmitry Z. Vinnitskiy、Nadezhda E. Ustyuzhanina、Andrey S. Dmitrenok、Alexander S. Shashkov、Nikolay E. Nifantiev

  DOI：10.1016/j.carres.2016.11.015

  日期：2017.1

  3-O-benzoyl-2-deoxy-2-N-phthalimido-D-galactoside by 2-O-benzyl-3,4-di-O-chloracetyl-L-fucosyl trichloracetimidate in the presence of TMSOTf gave a 1:1 mixture of the corresponding alpha- and beta-isomeric disaccharides, while the use of structurally related fucosyl bromide donor with promotion by Bu4NBr led to the formation of desired alpha-isomeric disaccharide exclusively. Selective removal of orthogonal

  合成未取代的和6-O-α-L-岩藻糖基化的丙基2-乙酰氨基-2-脱氧-β-D-吡喃半乳糖苷及其选择性地被O-硫酸化（均在GalNAc和Fuc单元中）的衍生物，作为代表岩藻糖基化片段的模型化合物海参中的硫酸软骨素（FCS）。将过-O-乙酰化的2-脱氧-2-N-邻苯二甲酰亚胺基-D-吡喃葡萄糖用作制备所有含2-乙酰氨基-2-脱氧-D-吡喃半乳糖苷的产物的关键前体。2-O-苄基-3,4-二-O-氯乙酰基-L-岩藻糖基三氯乙酰亚氨酸酯在3-O-苯甲酰基-2-脱氧-2-N-邻苯二甲酰亚胺-D-半乳糖苷的6-O-糖基化反应中的尝试TMSOTf的存在产生了相应的α-异构体和β-异构体二糖的1：1混合物，而使用结构相关的岩藻糖基溴供体并通过Bu4NBr促进导致仅形成所需的α-异构二糖。选择性去除正交O-保护基允许随后在GalNAc和Fuc单元上进行O-硫酸化。进一步除去保护基团得到目标产物，通过1 H和13
• <i>N</i>-Bromosuccinimide-Mediated Conversion of Allyl Glycosides to Glycosyl Hemiacetals
  作者：Rajib Panchadhayee、Anup Kumar Misra

  DOI：10.1080/07328301003664887

  日期：2010.3.22

  A novel reaction condition has been developed for the hydrolysis of differentially functionalized allyl glycosides to their corresponding glycosyl hemiacetal derivatives in the presence of N-bromosuccinimide (NBS). The reaction condition is exceptionally fast, mild, and compatible with most of the functional groups used in the oligosaccharide synthesis, and yields were excellent.

  在N-溴代琥珀酰亚胺（NBS）存在下，已经开发出了一种新的反应条件，用于将不同功能化的烯丙基糖苷水解为它们相应的糖基半缩醛衍生物。反应条件异常快速，温和，并且与寡糖合成中使用的大多数官能团相容，并且收率非常好。
• Acetylated methyl glucopyranuronate trichloroacetimidate as a glycosyl donor for efficient synthesis of disaccharides
  作者：Sameh E Soliman、Rafik W Bassily、Ramadan I El-Sokkary、Mina A Nashed

  DOI：10.1016/s0008-6215(03)00317-3

  日期：2003.10

  Allyl (methyl 2,3,4-tri-O-acetyl-beta-D-glucopyranosyl uronate)-(1 --> 3)-4,6-O-benzylidene-2-deoxy-2-phthalimido-(3-D-glucopyranoside (4) and benzyl (methyl 2,3,4-tri-O-acetyl-beta-D-glucopyranosyl uronate)-(1 --> 3)-4,6-O-benzylidene-2-deoxy-2-phthalimido-beta-D-glucopyranoside (5) have been efficiently synthesized by coupling allyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-beta-D-glucopyranoside (2) or benzyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-alpha-D-glucopyranoside (3) with methyl (2,3,4-tri-O-acetyl-1-OtrichloroacetimidOyl)-alpha-D-glucopyranuronate (1), respectively, using trimethylsilyl triflate as promoter. (C) 2003 Elsevier Ltd. All rights reserved.