p-methoxyphenyl 3,4-di-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranoside | 395072-12-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl 3,4-di-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
• 英文别名: p-methoxyphenyl 3,4-di-O-benzoyl-2-deoxy-2-phthalimdo-β-D-glucopyranoside；[(2R,3S,4R,5R,6S)-4-benzoyloxy-5-(1,3-dioxoisoindol-2-yl)-2-(hydroxymethyl)-6-(4-methoxyphenoxy)oxan-3-yl] benzoate
• CAS: 395072-12-5
• 化学式: C₃₅H₂₉NO₁₀
• 分子量: 623.616
• InChiKey: RVRFOPGXJNZMFR-RMBAAUDXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  46
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  138
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl 3,4-di-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 、 乙酰氯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 p-methoxyphenyl 3,4-di-O-benzoyl-6-O-(3,4-di-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  A Synthetic Pentasaccharide with GTPase Activity

  摘要：

  [GRAPHICS]The design, synthesis, and preliminary evaluation of the first example of synthetic pentasaccharide (1) that shows marked rate enhancement and specificity for the hydrolysis of GTP to GDP and orthophosphate (OP) are reported. At the concentration ratios of GTP/1 = 3.6 and GTP/Mg2+ = 1 (pH 7.1, 50 degreesC), a rate enhancement of about 500-fold was obtained.

  DOI：

  10.1021/ol010257h
• 作为产物：
  描述：

  4-methoxyphenyl 2-deoxy-2-phthalimido-β-D-glucopyranoside 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 perchloric acid on silica gel 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成 p-methoxyphenyl 3,4-di-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  An efficient and recyclable catalyst for the cleavage of tert-butyldiphenylsilyl ethers

  摘要：

  An efficient, chemoselective, and environment-friendly method for the deprotection of tert-butyldiphenylsilyl ethers mediated by triflic acid supported on silica gel is reported. A wide range of tert-butyldiphenylsilyl ethers derived from carbohydrate and saponin residues can be smoothly cleaved in the presence of various types of other protecting groups in good to excellent yields in acetonitrile. This heterogeneous reaction does not require aqueous workup, and the supported catalyst can be readily recycled. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.02.021

文献信息

• 8-(Methyltosylaminoethynyl)-1-naphthyl (MTAEN) Glycosides: Potent Donors in Glycosides Synthesis
  作者：Si-Yu Zhou、Xin-Ping Hu、Hui-Juan Liu、Qing-Ju Zhang、Jin-Xi Liao、Yuan-Hong Tu、Jian-Song Sun

  DOI：10.1021/acs.orglett.1c04102

  日期：2022.1.21

  efficient glycosylation protocol has been established. The MTAEN glycosylation protocol exhibits the merits of shelf-stable donors, mild catalytic promotion conditions, considerably extended substrate scope encompassing both free alcohols, silylated alcohols, nucleobases, primary amides, and C-type nucleophile acceptors, and applicability to various one-pot strategies for highly efficient synthesis of oligosaccharides

  以 8-(methyltosylaminoethynyl)-1-naphthyl (MTAEN) 糖苷为供体，建立了一种新颖高效的糖基化方案。MTAEN 糖基化方案具有货架稳定供体、温和的催化促进条件、大大扩展底物范围（包括游离醇、甲硅烷基化醇、核碱基、伯酰胺和C型亲核受体）的优点，并适用于各种一锅策略用于高效合成寡糖，例如正交一锅法、单催化剂一锅法和受体反应性控制一锅法。
• Synthesis of 1,6-anhydro sugars catalyzed by silica supported perchloric acid
  作者：Yuexing Chun、Shiqiang Yan、Xiangpeng Li、Ning Ding、Wei Zhang、Peng Wang、Ming Li、Yingxia Li

  DOI：10.1016/j.tetlet.2011.09.055

  日期：2011.11

  A new and efficient method for the preparation of 1,6-anhydro sugars using silica supported perchloric acid as a catalyst is described. The catalyst is heterogeneous and 1,6-anhydro sugars could be formed within a few minutes with good yields.

  描述了使用二氧化硅负载的高氯酸作为催化剂制备1，6-脱水糖的新的有效方法。该催化剂是非均相的，并且可以在几分钟内以良好的产率形成1，6-脱水糖。
• An efficient method for the cleavage of <i>tert</i>-butyldiphenylsilyl ethers catalyzed by 1,3-dibromo-5,5-dimethylhydantoin
  作者：Zong Han

  DOI：10.1080/07328303.2022.2031206

  日期：2022.1.2

  Abstract An efficient method for the deprotection of tert-butyldiphenylsilyl (TBDPS) ethers using 1,3-dibromo-5,5-dimethylhydantoin (DBH) as catalyst and dimethyl sulfoxide (DMSO) as solvent has been established. This method is useful for many kinds of compounds, such as carbohydrates, steroids, benzyl alcohols and primary fatty alcohols. Substrates bearing acetates, benzoates, pivaloates, mesylates, and benzyl

  摘要 建立了以1,3-二溴-5,5-二甲基乙内酰脲(DBH)为催化剂、二甲基亚砜(DMSO)为溶剂的叔丁基二苯基甲硅烷基(TBDPS)醚脱保护的有效方法。该方法适用于多种化合物，例如碳水化合物、类固醇、苯甲醇和脂肪伯醇。带有乙酸盐、苯甲酸盐、新戊酸盐、甲磺酸盐和苄基醚和对甲氧基苄基醚的底物是相容的。
• One-Pot Synthesis of Glucosamine Oligosaccharides
  作者：Micha Fridman、Dmitry Solomon、Shay Yogev、Timor Baasov

  DOI：10.1021/ol017054d

  日期：2002.1.1

  2-amino-2-deoxy glucose by selective introduction of different N-protecting (NPhth and NHTroc) and anomeric leaving groups (ethylthio and phenylthio) enabled highly efficient oligosaccharide synthesis in a one-pot manner. One-pot sequential glycosylation of three and four units of 2-amino-2-deoxy glucose gave trisaccharides and tetrasaccharide in 50-81% yields.

  [反应：见正文]通过选择性引入不同的N-保护基（NPhth和NHTroc）和异头离去基团（乙硫基和苯硫基）来调节衍生自2-氨基-2-脱氧葡萄糖的糖基供体的反应性，可实现高效的寡糖合成一锅法。一锅顺序糖基化的三个和四个单元的2-氨基-2-脱氧葡萄糖依次产生三糖和四糖，收率为50-81％。
• An efficient and recyclable catalyst for the cleavage of tert-butyldiphenylsilyl ethers
  作者：Shiqiang Yan、Ning Ding、Wei Zhang、Peng Wang、Yingxia Li、Ming Li

  DOI：10.1016/j.carres.2012.02.021

  日期：2012.6

  An efficient, chemoselective, and environment-friendly method for the deprotection of tert-butyldiphenylsilyl ethers mediated by triflic acid supported on silica gel is reported. A wide range of tert-butyldiphenylsilyl ethers derived from carbohydrate and saponin residues can be smoothly cleaved in the presence of various types of other protecting groups in good to excellent yields in acetonitrile. This heterogeneous reaction does not require aqueous workup, and the supported catalyst can be readily recycled. (C) 2012 Elsevier Ltd. All rights reserved.