[(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 | 251348-06-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(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
• CAS: 251348-06-8
• 化学式: C₄₄H₄₃Cl₅N₂O₁₆
• 分子量: 1033.09
• InChiKey: VYMOIZIZMHFISD-JSUDYGOLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  67
• 可旋转键数：
  23
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  222
• 氢给体数：
  1
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  [(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 、 [(2R,3R,4S,5S,6S)-3,4,5-Tris-benzyloxy-6-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-octyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-yl]-methanol 在 三乙基硅基三氟甲磺酸酯 作用下， 以62%的产率得到[(2R,3S,4S,5R,6S)-5-acetyloxy-2-(acetyloxymethyl)-4-(2-chloroacetyl)oxy-6-[(2R,3S,4R,5R,6R)-5-(1,3-dioxoisoindol-2-yl)-6-[[(2R,3R,4S,5S,6S)-6-[[(2R,3R,4S,5S,6R)-6-octoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy]-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy]-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-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：

  2-(三甲基硅烷基)乙基beta-吡喃半乳糖苷 在 吡啶 、 2,3,5-三甲基吡啶 、 1,1-二氯甲醚 、 4 A molecular sieve 、 camphor-10-sulfonic acid 、 silver trifluoromethanesulfonate 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 、 zinc(II) chloride 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 26.0h， 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

文献信息

• Expedient synthesis of a series of N-acetyllactosamines
  作者：J.C. McAuliffe、M. Fukuda、O. Hindsgaul

  DOI：10.1016/s0960-894x(99)00485-0

  日期：1999.10

  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.