methyl 6-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-β-D-galactopyranoside | 111462-66-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-β-D-galactopyranoside
• 英文别名: β-D-GlcpNAc-(1->6)-β-D-Galp-OMe；N-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methoxy]oxan-3-yl]acetamide
• CAS: 111462-66-9
• 化学式: C₁₅H₂₇NO₁₁
• 分子量: 397.379
• InChiKey: UXYSKKBVNODRDW-MUBICPRTSA-N

物化性质

• 沸点：
  747.5±60.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.6
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  187.4
• 氢给体数：
  7.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  (3aR)-2-甲基-5alpha-(乙酰氧基甲基)-6beta,7alpha-二乙酰氧基-3Aalpha,6,7,7Aalpha-四氢-5H-吡喃并[3,2-d]恶唑 在 palladium on activated charcoal 氢气 、 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 溶剂黄146 、 1,2-二氯乙烷 为溶剂， 25.0~72.0 ℃ 、345.0 kPa 条件下， 反应 102.0h， 生成 methyl 6-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-β-D-galactopyranoside
  参考文献：
  名称：

  合成粘蛋白片段。甲基6-O-（2-乙酰氨基-2-脱氧-β-D-Glycopyranosyl）-β-D-吡喃半乳糖苷，甲基3,4-二-O-（2-乙酰氨基-2-脱氧-β-D-Glycopyranosyl ）-β-D-吡喃半乳糖苷和甲基O-（2-乙酰氨基-2-脱氧-β-D-吡喃吡喃糖基）-（1å3）-O-β-D-D-吡喃半乳糖苷-（1å3）-O- （2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖基）-（1å3）-β-D-吡喃半乳糖苷

  摘要：

  甲基2,6-二-O-苄基-β-D-吡喃半乳糖苷与2-甲基-（3,4,6-三-O-乙酰基-1,2-二脱氧-α-D-吡喃吡喃）-[在对甲苯磺酸的存在下，在1,2-二氯乙烷中的2,1-d] -2-恶唑啉（1）提供了一种三糖衍生物，该衍生物经脱乙酰化后得到甲基3,4-二-O-（2 -乙酰氨基-2-脱氧-β-D-吡喃葡萄糖基）-2，6-二-O-苄基-bet aD-吡喃半乳糖苷（5）。5个苄基的氢解得到标题三糖（6）。甲基2,3-二-O-苄基-β-D-吡喃半乳糖苷与1的类似缩合反应可得到部分保护的二糖衍生物，在O-脱乙酰基反应后进行氢解，得到甲基6-O-（2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖基）-β-D-吡喃半乳糖苷（10）。3-O-（2-乙酰氨基-4,6-O-亚苄基-2-脱氧-β-D-吡喃吡喃糖基）-2,4的缩合，6-三-O-苄基-β-D-吡喃半乳糖苷与3-O-（2-乙酰氨基-3,4,6-三-

  DOI：

  10.1016/0008-6215(87)84004-1

文献信息

• Enzymic synthesis of di- and tri-saccharide glycosides, using glycosidases and β-d-galactoside 3-α-sialyl-transferase
  作者：Kurt G.I. Nilsson

  DOI：10.1016/0008-6215(89)84053-4

  日期：1989.6

  acceptor, beta-D-Galp-(1----3)-beta-D-GlcpNAc-OMe was formed in only slightly excess over teh analogous beta-(1----4)-linked glycoside. The use of beta-D-galactosidase and beta-D-galactoside 3-alpha-sialyltransferase in sequence provided a convenient route to the trisaccharide glycosides alpha-D-Neup5Ac-(2----3)-beta-D-Galp-(1----3)-alpha-D-GalpNAc-OEt, alpha-D-Neup5Ac-(2----3)-beta-D-Galp-(1----3)-beta-D-GalpNAc-OE

  通过使用糖苷酶作为催化剂，从适当的供体和受体糖苷中获得以下二糖苷的收率为10％至35％：α-D-Galp-（1 ---- 3）-alpha-D-GalpNAc-OEt（alpha -D-半乳糖苷酶），beta-D-Galp-（1 ---- 3）-alpha-D-GalpNAc-OEt和beta-D-Galp-（1 ---- 3）-beta-D-GalpNAc- OEtBr（β-D-半乳糖苷酶），β-D-GlcpNAc-（1 ---- 6）-β-D-Galp-OMe和β-D-GlcpNAc-（1 ---- 6）-alpha-D -Manp-OMe（β-N-乙酰氨基葡糖苷酶）。使用β-D-GlcpNAc-OEtSiMe3作为受体时，β-D-半乳糖苷酶几乎完全提供了β-D-Galp-（1 ---- 3）-β-D-GlcpNAc-OEtSiMe3，而使用β-D- GlcpNAc-OMe作为受体，形成的β-D-Galp-（1
• Stannylene Activation in Glycoside Synthesis: Regioselective Glycosidations at the Primary Position of Galactopyranosides Unprotected in the 2-, 3-, 4-, and 6-Positions
  作者：Per J. Garegg、Jean-Luc Maloisel、Stefan Oscarson

  DOI：10.1055/s-1995-3918

  日期：1995.4

  Stannylene activation with dibutyltin oxide of methyl D-galactopyranosides and of methyl β-D-glucopyranoside, respectively, followed by glycosidation with 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl bromide promoted by tetrabutylammonium iodide, or followed by glycosidation with ethyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside, or ethyl 2,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside, or ethyl 2,3,4,6-tetra-O-benzoyl-1-thio-α-D-mannopyranoside, the latter four glycosyl donors being promoted by dimethyl(methylthio)sulfonium trifluoromethanesulfonate (DMTST), led to regioselective glycosidation at the 6-OH of the stannylene glycosyl acceptors. This selectivity was not observed in the absence of stannylene activation.

  分别用二丁基氧化锡活化甲基 D-吡喃半乳糖苷和甲基 δ-D-吡喃葡萄糖苷，然后用 2,3,4,6- O-四苄基-δ-D-吡喃葡萄糖基溴化物在四丁基碘化铵的促进下进行糖化，或用乙基 2,3,4,6- O-四苯甲酰基-1-硫代-δ-D-吡喃葡萄糖苷进行糖化、或乙基 2,3,4,6-O-四乙酰基-2-脱氧-2-酞酰亚胺基-1-硫代-δ-D-吡喃葡萄糖苷，或乙基 2,3,4,6-O-四苯甲酰基-1-硫代-δ-D-吡喃甘露糖苷、在三氟甲磺酸二甲基（甲硫基）锍（DMTST）的促进下，后四种糖基供体在链烯糖基受体的 6-OH 处发生了区域选择性糖苷化反应。在没有锡烯活化的情况下，则观察不到这种选择性。
• Enzymic synthesis of HexNAc-containing disaccharide glycosides
  作者：Kurt G.I. Nilsson

  DOI：10.1016/0008-6215(90)84022-m

  日期：1990.9

  The following disaccharide glycosides were obtained from the appropriate donor and acceptor glycosides by employing glycosidases from the mollusc Chamelea gallina as catalysts: alpha-D-Galp-OMe (N-acetyl-alpha-D- galactosaminidase), beta-D-GalpNAc-(1----3)-beta-D-Galp-OMe, beta-D-GlcpNAc-(1----3)-beta-D-Galp-OMe, and beta-D-GlcpNAc-(1----6)-alpha-D-Manp-OMe (N-acetyl-beta-D-hexosaminidase). The regioselectivity of the N-acetyl-beta-D-hexosaminidase-catalysed reactions depended on the anomeric configuration of the acceptor. Thus, alpha-D-Galp-OMe gave beta-D-GlcpNAc- (1----6)-alpha-D-Galp-OMe almost exclusively, whereas beta-D-Galp-OMe gave beta-D-GlcpNAc-(1----3)-beta-D-Galp-OMe and beta-D-GlcpNAc-(1----6)-beta-D-Galp-OMe in almost equal amounts. The isolation of the products by chromatography was straightforward.