methyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>3)-2-acetamido-6-O-benzyl-2-deoxy-β-D-glucopyranoside | 98807-92-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>3)-2-acetamido-6-O-benzyl-2-deoxy-β-D-glucopyranoside
• 英文别名: methyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside；Gal2Ac3Ac4Ac6Ac(b1-3)[Bn(-6)]b-GlcNAc1Me；[(2R,3S,4S,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-5-hydroxy-2-methoxy-6-(phenylmethoxymethyl)oxan-4-yl]oxy-3,4,5-triacetyloxyoxan-2-yl]methyl acetate
• CAS: 98807-92-2
• 化学式: C₃₀H₄₁NO₁₅
• 分子量: 655.653
• InChiKey: DDRZQJFVLJXAEN-XRAAFVHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  46
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  201
• 氢给体数：
  2
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  methyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>3)-2-acetamido-6-O-benzyl-2-deoxy-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以95%的产率得到
  参考文献：
  名称：

  Synthetic Analogs of the Lewis^b-Tetrasaccharide and their Binding to Griffonia Simplicifolia Lectin-Part I

  摘要：

  刘易斯B四糖特异性地结合到刺槐豆凝集素GS-IV上。为了获得更紧密结合的衍生物，我们合成了一系列这种四糖的类似物，并研究了它们与凝集素的结合。本文（系列中的第一部分，共两部分）描述了对半乳糖单元（b）在6位进行改变的类似物的合成及其结合研究。尽管这个位置在晶体结构中并不直接与蛋白质接触，但结合对这些取代非常敏感。

  DOI：

  10.1055/s-2003-40329
• 作为产物：
  描述：

  methyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>3)-2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 在 盐酸 、 3 A molecular sieve 、 sodium cyanoborohydride 作用下， 以 乙醚 为溶剂， 反应 0.25h， 以94%的产率得到methyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>3)-2-acetamido-6-O-benzyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of methyl O-(β-d-galactopyranosyl)-(1→3)-O-[α-l-fucopyranosyl-(1→4)]-2-acetamido-2-deoxy-6-O-sulfoβ -d-glucopyranoside sodium salt as a potential ligand for selectin molecules

  摘要：

  DOI：

  10.1016/0008-6215(94)00258-h

文献信息

• The synthesis of monodeoxy derivatives of lacto-N-biose I and N-acetyl-lactosamine to serve as substrates for the differentiation of α-l-fucosyl transferases
  作者：Deveshwari P. Khare、Ole Hindsgaul、Raymond U. Lemieux

  DOI：10.1016/0008-6215(85)85204-6

  日期：1985.2

  β- d -Gal- and β- d -GlcNAc-α- l -fucosyl transferases. It is suggested that the enzymes accept the substrates in near their most favorable conformations and that the binding involves both polar and nonpolar interactions with topographical features near the hydroxyl group which undergoes substitution. It appears that, depending on the transferase, the recognition may or may not include both the sugar

  摘要β-d -Gal-（1→3）-4-deoxy-β-d-GlcNAcOR和β-d -Gal-（1→4）-3-deoxy-β-d-GlcNAcOR的化学合成，其中报告了R =（CH2）8COOMe和Me。此外，2-deoxy-β-d-Gal-（1→3）-β-d-GlcNAcO（ ）8COOMe和2-deoxy-β-d-Gal-（1→4）-β-d-GlcNAcO（合成CH 2）8 COOMe。关于这些化合物作为β-d-Gal-和β-d-GlcNAc-α-1-岩藻糖基转移酶的受体的行为，报道了来自其他实验室的初步结果。建议这些酶以其最有利的构象接受底物，并且该结合涉及极性和非极性相互作用，并具有在被取代的羟基附近的形貌特征。似乎取决于转移酶，识别可以包括或可以不包括两个糖单元。
• How the Substituent at O-3 of <i>N</i>-Acetylglucosamine Impacts Glycosylation at O-4: A Comparative Study
  作者：Jenifer L. Hendel、Jo-Wen Wang、Trudy A. Jackson、Karolyn Hardmeier、Richelle De Los Santos、France-Isabelle Auzanneau

  DOI：10.1021/jo901616p

  日期：2009.11.6

  protecting groups, β-linked or α-linked d or l sugars at O-3 is presented, using a per-O-acetylated α-d-glucosyl trichloroacetimidate donor under activation by BF3·OEt2. The presence of either an acyl or carbonate protecting group at O-3 did not impact the reactivity at O-4 with all glycosylations proceeding successfully. On the other hand, the presence of peracetylated sugars at O-3 of N-acetylglucosamine

  的4-OH的相对反应性的评估Ñ乙酰氨基葡萄糖受体轴承简单的保护基团，β联或α联d或升糖在O-3被呈现，使用以每个ö -acetylatedα- d - BF 3 ·OEt 2活化下的三氯乙酰氨基葡萄糖葡萄糖供体。在O-3处存在酰基或碳酸酯保护基团不会影响O-4处的反应性，所有糖基化均会成功进行。另一方面，在N-乙酰基葡糖胺受体的O-3处过乙酰化的糖的存在确实影响了4-OH的反应性。α- d -Man，β- d的受体-Gal或O-3处的β- d -Glc立即反应。相比之下，带有β- 1- Fuc，α - 1 - Fuc或α- 1- Rha的受体缓慢地进行糖基化，并且从反应混合物中回收未反应的受体。对在葡糖胺残基的O-3处带有过乙酰化的β- d- Gal或β- 1 -Fuc的二糖受体和三糖产物进行的系统研究表明，对于这两个受体，在岩藻糖苷键周围必须进行构象重新定向有助于降低β-岩藻糖基化受体的反应性。受主轴承β联d
• Glycosylation of <i>N</i>-Acetylglucosamine:  Imidate Formation and Unexpected Conformation
  作者：Liang Liao、France-Isabelle Auzanneau

  DOI：10.1021/ol034669x

  日期：2003.7.1

  [GRAPHICS]Rhamnosylation in mild conditions of a disaccharide containing N-acetylglucosamine afforded the imidate 6 while at higher temperature and concentration of promoter trisaccharide 7 was isolated. The kinetic imidate 6 was independently rearranged in 50% yield to the thermodynamic trisaccharide 7. Comparative NMR studies of 7 in CDCl3 and DMSO-d(6) suggest the formation of a nonchair conformation in CDCl3. The structure of 7 was confirmed through the independent synthesis of the N-acetylacetamido trisaccharide 11.
• The Amide Group in <i>N</i>-Acetylglucosamine Glycosyl Acceptors Affects Glycosylation Outcome
  作者：Liang Liao、France-Isabelle Auzanneau

  DOI：10.1021/jo050707+

  日期：2005.8.1

  Glycosylation of a disaccharide containing N-acetylglucosamine with rhamnosyl and mannosyl trichloracetimidates under triethysilyl triflate catalysis led to the competitive formation of glycosyl imidates. While the rhamnosyl imidate could be rearranged to the thermodynamically favored trisaccharide, the mannosyl analogue was resistant to rearrangement. Glycosylation with perbenzylated thiorhamnosides activated with methyl triflate (MeOTf) gave the trisaccharide as well as the methyl imidate trisaccharide. The less reactive alpha-thioethyl donor led to a higher relative amount of methyl imidate trisaccharide to trisaccharide than the more reactive beta-thioglycoside. When using a more reactive thioethyl fucoside only the trisaccharide was obtained. Interestingly, the acceptor treated with MeOTf gave the N-methyl imidate that could be easily rhamnosylated and subsequently converted to the N-acetamido trisaccharide. This strategy to glycosylate O-4 of N-acetylglucosamine is under further investigation. Alternatively, bis-N-acetylation of the glucosamine prevented the formation of imidates and allowed the efficient synthesis of two Lewis A trisaccharide analogues.