1,3,6-tri-O-acetyl-2-azido-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranose | 68733-22-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,6-tri-O-acetyl-2-azido-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranose
• 英文别名: 1,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-azido-2-deoxy-β-D-glucopyranose；[(2R,3S,4R,5R,6S)-4,6-diacetyloxy-5-azido-3-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 68733-22-2
• 化学式: C₂₆H₃₅N₃O₁₇
• 分子量: 661.574
• InChiKey: XNCHAEIOCATQMJ-KBKHSNHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  46
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  226
• 氢给体数：
  0
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  1,3,6-tri-O-acetyl-2-azido-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranose 在 palladium on activated charcoal 氢气 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 Acetic acid (2S,3R,4R,5S,6R)-2-acetoxy-6-acetoxymethyl-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-3-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-4-yl ester
  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：

  Acetic acid (2R,3S,4R)-2-acetoxymethyl-5-azido-6-nitrooxy-3-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester 在 mercury(II) diacetate 、 lithium bromide 作用下， 以 乙腈 为溶剂， 反应 23.0h， 生成 1,3,6-tri-O-acetyl-2-azido-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranose
  参考文献：
  名称：

  Synthesis and anti-angiogenetic activity evaluation of N-(3-aryl acryloyl)aminosaccharide derivatives

  摘要：

  In order to find novel potent inhibitors for signal pathways of FGF/FGFR, nineteen N-(3-aryl acryloyl)aminosaccharide derivatives were designed and synthesized based on the binding sites of FGF and oligosaccharides of heparin. Their structures were confirmed by IR, H-1 NMR, C-13 NMR, MS and elemental analysis. The nineteen target compounds were evaluated for biological activity against HUVEC cell. In vitro assays showed that compound 10s (IC50 = 5.3 mu M) exhibited comparable inhibitory effects on endothelial cell growth with topotecan (IC50 = 2.7 mu M). Compound 10s (10 mu g/egg) also showed obvious anti-angiogenetic activity in the in vivo chicken chorio allantoic membrane (CAM) assay, and the potency was similar to topotecan (10 mu g/egg). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.08.022

文献信息

• Synthesis of 2-amino-2-deoxyglycoses and 2-amino-2-deoxyglycosides from
  申请人：Chembiomed Ltd.

  公开号：US04195174A1

  公开（公告）日：1980-03-25

  O-acetylated glycals react with ceric ammonium nitrate in the presence of sodium azide to provide, in good yield, O-acetylated 2-azido-2-deoxy glycosyl nitrates. These nitrates can be used to prepare 2-amino-2-deoxy sugars, such as D-galactosamine and lactosamine. The O-acetylated 2-azido-2-deoxy glycosyl nitrates can alternately be converted to O-acetylated 2-azido-2-deoxy glycosyl halides which are useful in the preparation of O-acetylated 2-azido-2-deoxy glycosides, which in turn can be reduced to 2-amino-2-deoxy glycosides. Of particular interest are the syntheses of 2-amino-2-deoxy glycosides which correspond to the terminal units of the antigenic determinant for the human A blood group. Attachment of these glycosides to a solid support provides immunoabsorbents which efficiently and preferentially absorb anti-A antibodies from blood plasma.

  O-乙酰化的糖醛与偏铈铵硝酸盐在存在硝酸钠的情况下反应，产生良好产率的O-乙酰化2-叠氮基-2-脱氧糖基硝酸盐。这些硝酸盐可用于制备2-氨基-2-脱氧糖类，如D-半乳糖胺和乳糖胺。O-乙酰化的2-叠氮基-2-脱氧糖基硝酸盐可被转化为O-乙酰化的2-叠氮基-2-脱氧糖基卤化物，这些卤化物在制备O-乙酰化的2-叠氮基-2-脱氧糖苷时很有用，而后者可以还原为2-氨基-2-脱氧糖苷。特别感兴趣的是合成对应于人类A血型抗原决定簇的2-氨基-2-脱氧糖苷。将这些糖苷连接到固定支持体上可提供有效地吸附血浆中的抗A抗体的免疫吸附剂。