allyl 2-acetamido-6-O-benzoyl-3-O-benzyl-2-deoxy-β-D-glucopyranoside | 399036-09-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2-acetamido-6-O-benzoyl-3-O-benzyl-2-deoxy-β-D-glucopyranoside
• CAS: 399036-09-0
• 化学式: C₂₅H₂₉NO₇
• 分子量: 455.508
• InChiKey: BCBAOBJHQWMYLD-BBPVLXATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.22
• 重原子数：
  33.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  103.32
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  allyl 2-acetamido-6-O-benzoyl-3-O-benzyl-2-deoxy-β-D-glucopyranoside 在 sodium azide 、 18-冠醚-6 、 4 A molecular sieve 、 silver trifluoromethanesulfonate 、 臭氧 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 103.0h， 生成 (2S,3R,4S,5S,6R)-2-(((2R,3S,4R,5R,6R)-5-acetamido-6-(2-azidoethoxy)-2-((benzoyloxy)methyl)-4-(benzyloxy)tetrahydro-2H-pyran-3-yl)oxy)-4-acetoxy-6-((benzoyloxy)methyl)tetrahydro-2H-pyran-3,5-diyl dibenzoate
  参考文献：
  名称：

  Study of glycosylation with N-trichloroacetyl-d-glucosamine derivatives in the syntheses of the spacer-armed pentasaccharides sialyl lacto-N-neotetraose and sialyl lacto-N-tetraose, their fragments, and analogues

  摘要：

  The syntheses of 2-aminoethyl glycosides of the pentasaccharides Neu5Ac-alpha (2 --> 3)-Gal-beta (3(1 --> 4)-GlcNAc-beta (3(1 --> 3)-Gal-beta (1 --> 4)-Glc and Neu5Ac-alpha (2 --> 3)-Gal-beta (1 --> 3)-GlcNAc-beta (1 --> 3)-Gal-beta (1 --> 4)-Glc, their asialo di-, tri-, and tetrasaccharide fragments, and analogues included a systematic study of glycosylation with variously protected mono- and disaccharide donors derived from N-trichloroacetyl-D-glucosamine of galactose, lactose, and lactosamine glycosyl acceptors bearing benzoyl protection around the OH group to be glycosylated. Despite the. low reactivity of these acceptors, stereo specificity and good to excellent yields were obtained with NIS-TfOH-activated thioglycoside donors of such type, or with AgOTf-activated glycosyl bromides, while other promotors, as well as a trichloroacetimidate donor, were less effective, and a beta -acetate donor was inactive. In NIS-TfOH-promoted glycosylation with the thioglycosides, the use of TfOH in catalytic amount led to rapid formation of the corresponding oxazoline, but the quantity of TfOH necessary for further efficient coupling with an acceptor depended on the reactivity of the donor, varying from 0.07 equiv for a 3,6-di-O-benzylated monosaccharide derivative to 2.1 equiv for a peracetylated disaccharide one. In the glycosylation products, the N-trichloroacetyl group was easily converted into N-acetyl by alkaline hydrolysis followed by N-acetylation. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00213-0
• 作为产物：
  描述：

  烯丙基2-乙酰氨基-3-O-苄基-2-脱氧吡喃己糖苷 、 苯甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到allyl 2-acetamido-6-O-benzoyl-3-O-benzyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Study of glycosylation with N-trichloroacetyl-d-glucosamine derivatives in the syntheses of the spacer-armed pentasaccharides sialyl lacto-N-neotetraose and sialyl lacto-N-tetraose, their fragments, and analogues

  摘要：

  The syntheses of 2-aminoethyl glycosides of the pentasaccharides Neu5Ac-alpha (2 --> 3)-Gal-beta (3(1 --> 4)-GlcNAc-beta (3(1 --> 3)-Gal-beta (1 --> 4)-Glc and Neu5Ac-alpha (2 --> 3)-Gal-beta (1 --> 3)-GlcNAc-beta (1 --> 3)-Gal-beta (1 --> 4)-Glc, their asialo di-, tri-, and tetrasaccharide fragments, and analogues included a systematic study of glycosylation with variously protected mono- and disaccharide donors derived from N-trichloroacetyl-D-glucosamine of galactose, lactose, and lactosamine glycosyl acceptors bearing benzoyl protection around the OH group to be glycosylated. Despite the. low reactivity of these acceptors, stereo specificity and good to excellent yields were obtained with NIS-TfOH-activated thioglycoside donors of such type, or with AgOTf-activated glycosyl bromides, while other promotors, as well as a trichloroacetimidate donor, were less effective, and a beta -acetate donor was inactive. In NIS-TfOH-promoted glycosylation with the thioglycosides, the use of TfOH in catalytic amount led to rapid formation of the corresponding oxazoline, but the quantity of TfOH necessary for further efficient coupling with an acceptor depended on the reactivity of the donor, varying from 0.07 equiv for a 3,6-di-O-benzylated monosaccharide derivative to 2.1 equiv for a peracetylated disaccharide one. In the glycosylation products, the N-trichloroacetyl group was easily converted into N-acetyl by alkaline hydrolysis followed by N-acetylation. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00213-0

文献信息

• Synthesis of some 2-alkoxy glyco-[2,1-d]-2-oxazolines and evaluation of their glycosylation reactivity
  作者：Sergey S. Pertel、Leonid O. Kononov、Alexander I. Zinin、Vasily Ja. Chirva、Elena S. Kakayan

  DOI：10.1016/j.carres.2012.03.026

  日期：2012.7

  The synthesis of the title compounds using intramolecular nucleophilic substitution reactions in the molecules of the corresponding 2-alkoxycarbonylamino-2-deoxy glucosyl halides was studied. It was found that in contrast to the 2-alkyl (aryl) glyco-[2,1-d]-2-oxazolines, the synthesis of the target 2-alkoxy glyco-[2,1-d]-2-oxazolines was possible only in highly basic media. The synthesized 2-alkoxy

  研究了使用分子内亲核取代反应在相应的2-烷氧基羰基氨基-2-脱氧葡糖基卤化物的分子中合成标题化合物。发现与2-烷基（芳基）糖-[2,1-d] -2-恶唑啉相反，目标2-烷氧基糖-[2,1-d] -2-恶唑啉的合成为只有在高度基础的媒体中才有可能。合成的2-烷氧基恶唑啉衍生物证明是活性的糖基供体，并且在非常温和的条件下用于弱质子酸催化的立体选择性1,2-反式糖基化反应，从而防止了异构化和其他副反应。作为这种糖基化的结果，形成了含有氨基甲酸酯N-保护基的糖苷和寡糖衍生物。