p-tolyl (2-acetamido-4,6-di-O-tert-butyldimethylsilyl-2,3-N,O-carbonyl-2-deoxy-α-D-galactopyranosyl)-(1->4)-2-acetamido-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-1-thio-α-D-galactopyranoside | 1242060-87-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-tolyl (2-acetamido-4,6-di-O-tert-butyldimethylsilyl-2,3-N,O-carbonyl-2-deoxy-α-D-galactopyranosyl)-(1->4)-2-acetamido-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-1-thio-α-D-galactopyranoside
• 英文别名: (3aR,4R,6R,7R,7aR)-7-[[(3aR,4R,6R,7R,7aR)-3-acetyl-7-[tert-butyl(dimethyl)silyl]oxy-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-oxo-4,6,7,7a-tetrahydro-3aH-pyrano[3,4-d][1,3]oxazol-4-yl]oxy]-3-acetyl-4-(4-methylphenyl)sulfanyl-6-(phenylmethoxymethyl)-4,6,7,7a-tetrahydro-3aH-pyrano[3,4-d][1,3]oxazol-2-one
• CAS: 1242060-87-2
• 化学式: C₄₄H₆₄N₂O₁₂SSi₂
• 分子量: 901.235
• InChiKey: BNLKMYYWRAXMNF-AELZGUPMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.02
• 重原子数：
  61
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  174
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  p-tolyl (2-acetamido-4,6-di-O-tert-butyldimethylsilyl-2,3-N,O-carbonyl-2-deoxy-α-D-galactopyranosyl)-(1->4)-2-acetamido-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-1-thio-α-D-galactopyranoside 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  A highly α-selective glycosylation for the convenient synthesis of repeating α-(1→4)-linked N-acetyl-galactosamine units

  摘要：

  The repeating GalpNAc-alpha-(1 -> 4)-GalpNAc unit is part of a series of essential structures that can be found in many important biomolecules such as the glycoproteins and the O-antigenic polysaccharides of clinically important bacterial strains. In this paper, we describe an exclusive alpha-selective glycosylation reaction, using a 4,6-di-O-tert-butyldimethylsilyl-N-acetyloxazolidinone-protected thioglycoside as the glycosyl donor, under pre-activation conditions, with only half amount of the promoter, providing the product GalpNAc-alpha-(1 -> 4)-GalpNAc in high isolated yield. This reaction can be also applied to increasing the length of the repeating structure, which is of significant use in further synthesis of branched or linear oligosaccharides. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.05.031
• 作为产物：
  描述：

  p-tolyl 2-acetamido-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-1-thio-α-D-galactopyranoside 、 在 2,4,6-三叔丁基嘧啶 作用下， 以 二氯甲烷 为溶剂， 以22.6 mg的产率得到p-tolyl (2-acetamido-4,6-di-O-tert-butyldimethylsilyl-2,3-N,O-carbonyl-2-deoxy-α-D-galactopyranosyl)-(1->4)-2-acetamido-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-1-thio-α-D-galactopyranoside
  参考文献：
  名称：

  A highly α-selective glycosylation for the convenient synthesis of repeating α-(1→4)-linked N-acetyl-galactosamine units

  摘要：

  The repeating GalpNAc-alpha-(1 -> 4)-GalpNAc unit is part of a series of essential structures that can be found in many important biomolecules such as the glycoproteins and the O-antigenic polysaccharides of clinically important bacterial strains. In this paper, we describe an exclusive alpha-selective glycosylation reaction, using a 4,6-di-O-tert-butyldimethylsilyl-N-acetyloxazolidinone-protected thioglycoside as the glycosyl donor, under pre-activation conditions, with only half amount of the promoter, providing the product GalpNAc-alpha-(1 -> 4)-GalpNAc in high isolated yield. This reaction can be also applied to increasing the length of the repeating structure, which is of significant use in further synthesis of branched or linear oligosaccharides. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.05.031

文献信息

• A highly α-selective glycosylation for the convenient synthesis of repeating α-(1→4)-linked N-acetyl-galactosamine units
  作者：Lin Yang、Xin-Shan Ye

  DOI：10.1016/j.carres.2010.05.031

  日期：2010.8

  The repeating GalpNAc-alpha-(1 -> 4)-GalpNAc unit is part of a series of essential structures that can be found in many important biomolecules such as the glycoproteins and the O-antigenic polysaccharides of clinically important bacterial strains. In this paper, we describe an exclusive alpha-selective glycosylation reaction, using a 4,6-di-O-tert-butyldimethylsilyl-N-acetyloxazolidinone-protected thioglycoside as the glycosyl donor, under pre-activation conditions, with only half amount of the promoter, providing the product GalpNAc-alpha-(1 -> 4)-GalpNAc in high isolated yield. This reaction can be also applied to increasing the length of the repeating structure, which is of significant use in further synthesis of branched or linear oligosaccharides. (C) 2010 Elsevier Ltd. All rights reserved.