(2R,3S,4R,5R,6S)-5-Azido-4-benzyloxy-2-benzyloxymethyl-6-((2S,3S,4S,5R,6R)-2,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-ol | 246866-05-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4R,5R,6S)-5-Azido-4-benzyloxy-2-benzyloxymethyl-6-((2S,3S,4S,5R,6R)-2,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-ol
• 英文别名: (2R,3S,4R,5R,6S)-5-azido-4-phenylmethoxy-2-(phenylmethoxymethyl)-6-[(2S,3S,4S,5R,6R)-2,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]oxyoxan-3-ol
• CAS: 246866-05-7
• 化学式: C₅₄H₅₇N₃O₁₀
• 分子量: 908.061
• InChiKey: YSSGXVXZBWMLGG-PKTHEOBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  67
• 可旋转键数：
  23
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R,5R,6S)-5-Azido-4-benzyloxy-2-benzyloxymethyl-6-((2S,3S,4S,5R,6R)-2,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-ol 、 methyl (2S,4S,5R,6R)-5-acetamido-4-acetyloxy-2-[(2R,3S,4S,5R,6S)-3,5-diacetyloxy-2-(phenylmethoxymethyl)-6-(2,2,2-trichloroethanimidoyl)oxyoxan-4-yl]oxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate 在 三氟甲磺酸三甲基硅酯 、 MS 4 Angstroem 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到methyl (2S,4S,5R,6R)-5-acetamido-4-acetyloxy-2-[(2S,3R,4S,5S,6R)-3,5-diacetyloxy-2-[(2R,3S,4R,5R,6S)-5-azido-4-phenylmethoxy-2-(phenylmethoxymethyl)-6-[(2S,3S,4S,5R,6R)-2,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-6-(phenylmethoxymethyl)oxan-4-yl]oxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
  参考文献：
  名称：

  Syntheses of α-dystroglycan derived sialylated glycosyl amino acids carrying a novel mannosyl serine/threonine linkage

  摘要：

  An efficient access to the Fmoc protected glycosyl amino acids 20a-d which correspond to the unique sequence NeuNAc-alpha-(2,3)-Gal-beta-(1,4)-GlcNAc-beta-(1,2)-Man-alpha-Ser/Thr recently found in laminin-binding protein alpha-dystroglycan, is described. Tetrasaccharide donor 18 was constructed from monosaccharide blocks 2, 3, 8 and 9 and coupled with Ser/Thr derivatives 19a-d. Resultant glycosyl amino acid 20d was completely deprotected into 1a. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01361-1
• 作为产物：
  描述：

  benzyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside 在 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 MS 3 Angstroem 、 triflic azide 、 乙二胺 作用下， 以 二氯甲烷 、 乙腈 、 正丁醇 为溶剂， 生成 (2R,3S,4R,5R,6S)-5-Azido-4-benzyloxy-2-benzyloxymethyl-6-((2S,3S,4S,5R,6R)-2,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-ol
  参考文献：
  名称：

  Syntheses of α-dystroglycan derived sialylated glycosyl amino acids carrying a novel mannosyl serine/threonine linkage

  摘要：

  An efficient access to the Fmoc protected glycosyl amino acids 20a-d which correspond to the unique sequence NeuNAc-alpha-(2,3)-Gal-beta-(1,4)-GlcNAc-beta-(1,2)-Man-alpha-Ser/Thr recently found in laminin-binding protein alpha-dystroglycan, is described. Tetrasaccharide donor 18 was constructed from monosaccharide blocks 2, 3, 8 and 9 and coupled with Ser/Thr derivatives 19a-d. Resultant glycosyl amino acid 20d was completely deprotected into 1a. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01361-1

文献信息

• Syntheses of α-dystroglycan derived sialylated glycosyl amino acids carrying a novel mannosyl serine/threonine linkage
  作者：Joachim Seifert、Tomoya Ogawa、Yukishige Ito

  DOI：10.1016/s0040-4039(99)01361-1

  日期：1999.9

  An efficient access to the Fmoc protected glycosyl amino acids 20a-d which correspond to the unique sequence NeuNAc-alpha-(2,3)-Gal-beta-(1,4)-GlcNAc-beta-(1,2)-Man-alpha-Ser/Thr recently found in laminin-binding protein alpha-dystroglycan, is described. Tetrasaccharide donor 18 was constructed from monosaccharide blocks 2, 3, 8 and 9 and coupled with Ser/Thr derivatives 19a-d. Resultant glycosyl amino acid 20d was completely deprotected into 1a. (C) 1999 Elsevier Science Ltd. All rights reserved.