2,6-di-O-acetyl-3,4-di-O-chloroacetyl-α-D-galactopyranosyl chloride | 251348-05-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,6-di-O-acetyl-3,4-di-O-chloroacetyl-α-D-galactopyranosyl chloride
• 英文别名: ClAc(-3)[ClAc(-4)]a-Gal1Cl2Ac6Ac；[(2R,3S,4S,5R,6R)-5-acetyloxy-2-(acetyloxymethyl)-6-chloro-4-(2-chloroacetyl)oxyoxan-3-yl] 2-chloroacetate
• CAS: 251348-05-7
• 化学式: C₁₄H₁₇Cl₃O₉
• 分子量: 435.643
• InChiKey: PALDLDUXHKIGNY-YGEXGZRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,6-di-O-acetyl-3,4-di-O-chloroacetyl-α-D-galactopyranosyl chloride 在 2,3,5-三甲基吡啶 、 4 A molecular sieve 、 silver trifluoromethanesulfonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 [(2R,3S,4S,5R,6S)-5-acetyloxy-2-(acetyloxymethyl)-4-(2-chloroacetyl)oxy-6-[(2R,3S,4R,5R,6S)-5-(1,3-dioxoisoindol-2-yl)-4-phenylmethoxy-2-(phenylmethoxymethyl)-6-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl]oxyoxan-3-yl] 2-chloroacetate
  参考文献：
  名称：

  Expedient synthesis of a series of N-acetyllactosamines

  摘要：

  A series of poly-N-acetyllactosamines representative of those found on complex N-glycans was synthesized for use in the kinetic characterization of recently cloned glycosyltransferases. The syntheses involved the iterative addition of a selectively protected N-acetyllactosaminyl donor to an octyl alpha-D-mannopyranosyl-1,6-beta-mannopyranoside acceptor, followed by deprotection. In addition, non-reducing galactosyl residues were removed with beta-galactosidase to furnish GlcNAc terminated compounds. In this manner tetra- to octasaccharides were efficiently produced. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00485-0
• 作为产物：
  描述：

  Acetic acid (3aS,4R,7R,7aS)-6-acetoxy-4-acetoxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester 在 吡啶 、 1,1-二氯甲醚 、 溶剂黄146 、 zinc(II) chloride 作用下， 反应 2.0h， 生成 2,6-di-O-acetyl-3,4-di-O-chloroacetyl-α-D-galactopyranosyl chloride
  参考文献：
  名称：

  Expedient synthesis of a series of N-acetyllactosamines

  摘要：

  A series of poly-N-acetyllactosamines representative of those found on complex N-glycans was synthesized for use in the kinetic characterization of recently cloned glycosyltransferases. The syntheses involved the iterative addition of a selectively protected N-acetyllactosaminyl donor to an octyl alpha-D-mannopyranosyl-1,6-beta-mannopyranoside acceptor, followed by deprotection. In addition, non-reducing galactosyl residues were removed with beta-galactosidase to furnish GlcNAc terminated compounds. In this manner tetra- to octasaccharides were efficiently produced. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00485-0

文献信息

• Efficient synthesis of lactosaminylated core-2 O-glycans
  作者：Anup Kumar Misra、Minoru Fukuda、Ole Hindsgaul

  DOI：10.1016/s0960-894x(01)00550-9

  日期：2001.10

  A series of lactosaminylated oligosaccharides found in mucin type O-glycans was synthesized using a generalized block strategy. The synthesis involved the addition of a protected lactosamine donor to a partially protected T-disaccharide derivative. The nonreducing galactose residues of the deblocked oligosaccharide products could be removed by beta -galactosidase from jack bean to produce the corresponding GlcNAc terminated compounds. A series of tri- to hexasaccharides was thus efficiently produced. (C) 2001 Elsevier Science Ltd. All rights reserved.