2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2-deoxy-2-acetamido-1,3,4-tri-O-acetyl-α-D-glucopyranose | 36954-63-9

• 物质功能分类: 生物化工 - 糖类化合物 - 双糖
• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2-deoxy-2-acetamido-1,3,4-tri-O-acetyl-α-D-glucopyranose
• 英文别名: 2-acetamido-1,3,6-tri-O-acetyl-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-glucopyranose；hepta-O-acetyl-N-acetyl-D-lactosamine；O¹,O³,O⁶-triacetyl-2-acetylamino-O⁴-(tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-α-D-glucopyranose；O¹,O³,O⁶-Triacetyl-2-acetylamino-O⁴-(tetra-O-acetyl-β-D-galactopyranosyl)-2-desoxy-α-D-glucopyranose；N-Acetyllactosamineheptaacetate；[(2R,3S,4R,5R,6R)-5-acetamido-4,6-diacetyloxy-3-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 36954-63-9
• 化学式: C₂₈H₃₉NO₁₈
• 分子量: 677.614
• InChiKey: XKTWMUHXXMTTHP-LMNUNGBOSA-N

物化性质

• 熔点：
  213-217°C
• 沸点：
  728.6±60.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  47
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  241
• 氢给体数：
  1
• 氢受体数：
  18

安全信息

• 危险品标志：
  Xi
• WGK Germany：
  3
• 海关编码：
  29400090

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2-deoxy-2-acetamido-1,3,4-tri-O-acetyl-α-D-glucopyranose 在 三氟甲磺酸三甲基硅酯 、 4-甲基苯磺酸吡啶 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 6.5h， 生成 benzyl 2-acetamido-3,4-di-O-acetyl-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Novel Synthetic Approaches to Manβ1-4GLCNAc and Lex Units from N-Acetyllactosamine

  摘要：

  Regioselective protection of N-acetyllactosamine with triphenylmethyl (trityl) and pivaloyl groups afforded the corresponding 3, 2', 4'-tri- and 2',4'-dihydroxyl derivatives in a few steps, respectively; these derivatives were used efficiently for the syntheses of the title compounds from N-acetyllactosamine in 46% (7 steps) and 19% (8 steps) overall yields, respectively.

  DOI：

  10.1080/07328309808002347
• 作为产物：
  描述：

  (+)-2-acetamido-1,3-di-O-acetyl-2-deoxy-α-D-glucopyranoside 在 吡啶 、 氯仿 、 乙酸酐 作用下， 生成 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2-deoxy-2-acetamido-1,3,4-tri-O-acetyl-α-D-glucopyranose
  参考文献：
  名称：

  Okuyama, Tohoku Journal of Experimental Medicine, 1958, vol. 68, p. 313,314

  摘要：

  DOI：

文献信息

• Galacto, Gluco, Manno<i>,</i> and Disaccharide-Based <i>C-</i>Glycosides of 2-Amino-2-deoxy Sugars
  作者：Laura Grant、Yan Liu、Kenneth E. Walsh、Daryl S. Walter、Timothy Gallagher

  DOI：10.1021/ol0269695

  日期：2002.12.1

  underwent facile C-Se homolysis to provide the corresponding anomeric radicals, which were trapped with alkenes to give C-glycosides. This provides a general entry to alpha-C-glycosides based on 2-amino-2-deoxy sugars that is also applicable to disaccharide variants.

  [反应：见正文]从易得的前体开始，通过一或两个步骤的方法制备衍生自GalNAc，GlcNAc和ManNAc的硒代糖苷。对异头硒化物进行轻松的C-Se均质分解，以提供相应的异头自由基，这些自由基被烯烃捕获，得到C-糖苷。这提供了基于2-氨基-2-脱氧糖的α-C-糖苷的一般入口，其也适用于二糖变体。
• Preparation of linear oligosaccharides by a simple monoprotective chemo-enzymatic approach
  作者：Marco Filice、Jose M. Palomo、Paolo Bonomi、Teodora Bavaro、Roberto Fernandez-Lafuente、Jose M. Guisan、Marco Terreni

  DOI：10.1016/j.tet.2008.07.026

  日期：2008.9

  acetylated glycosyl donor, the glycosylation reaction with these glycosyl acceptors leads to peracetylated oligosaccharides. These compounds can be directly used as intermediates for the synthesis of glycopeptides used as antitumoral vaccines and, at the end of the process, can be easily fully deprotected in only one step. Thus, these key building blocks have been successfully used in glycosylation reactions

  已经开发出一种在单糖合成中涉及乙酰酯作为独特保护基的单保护方法。从过乙酰化的单糖和糖开始，通过使用高效且选择性的化学酶促“一锅”策略（固定化脂肪酶催化的区域选择性水解，然后进行化学酰基转移），可以使用仅用乙酰酯保护的不同碳水化合物受体实现。如果结合使用乙酰化的糖基供体，则与这些糖基受体的糖基化反应导致过乙酰化的寡糖。这些化合物可直接用作合成用作抗肿瘤疫苗的糖肽的中间体，并且在该过程结束时，仅一步即可轻松将其完全脱保护。因此，这些关键的结构单元已成功用于糖基化反应中，可以有效地构建过乙酰化的二糖（例如生物学相关的乳糖胺），以克为单位。随后，与用作糖受体的3OH-四乙酰基-α-d-半乳糖进行糖基化反应，可以合成过乙酰化的乳-N-新-四糖抗原的N-三糖前体。将该策略扩展到3OH-二乙酰半乳糖，已经合成了与T肿瘤相关的碳水化合物抗原的一种过乙酰化的前体。
• General and Chemoselective N-Transacylation of Secondary Amides by Means of Perfluorinated Anhydrides
  作者：Paola Rota、Pietro Allevi、Raffaele Colombo、Maria L. Costa、Mario Anastasia

  DOI：10.1002/anie.200906055

  日期：2010.3.1

  A direct route: The N‐transacylation of secondary amides to their perfluorinated analogues with the possibility of subsequent conversion into a normal amide is reported (see scheme). This reaction occurs in the presence of a variety of functional groups that are labile to the hydrolysis conditions required by classical N‐transacylation.

  直接途径：报道了仲酰胺经N-酰化成全氟化类似物的可能性，随后可能转化为正酰胺（见方案）。该反应在多种官能团的存在下发生，这些官能团对经典的N-酰化反应所需的水解条件不利。
• A convenient synthesis of N-acetyllactosamine
  作者：Jocelyne Alais、Alain Veyrières

  DOI：10.1016/s0008-6215(00)80763-6

  日期：1981.6
• A chemoenzymatic approach towards moenomycin structural analogues
  作者：Gerhard Range、Ralf Krähmer、Peter Welzel、Dietrich Müller、Guido F. Herrmann、Udo Kragl、Christian Wandrey、Astrid Markus、Yveline van Heijenoort、Jean van Heijenoort

  DOI：10.1016/s0040-4020(96)01116-7

  日期：1997.2

  The trisaccharide moenomycin analogue 1c has been synthesized. One starting material was N-acetyllactosamine obtained by an enzyme-catalyzed transglycosylation. 1c differs from moenomycin degradation product 1a only in two positions of unit C. In contrast to 1a the synthetic 1c is antibiotically inactive. (C) 1997, Elsevier Science Ltd.