Acetic acid (2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-((2S,3S,4S,5R,6R)-2,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester | 246866-00-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-((2S,3S,4S,5R,6R)-2,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester
• 英文别名: [(2R,3S,4R,5R,6S)-5-(1,3-dioxoisoindol-2-yl)-4-phenylmethoxy-2-(phenylmethoxymethyl)-6-[(2S,3S,4S,5R,6R)-2,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]oxyoxan-3-yl] acetate
• CAS: 246866-00-2
• 化学式: C₆₄H₆₃NO₁₃
• 分子量: 1054.2
• InChiKey: ZFWKNODVYKUBGZ-PTFZYDTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  78
• 可旋转键数：
  25
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  147
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-((2S,3S,4S,5R,6R)-2,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester 在 乙二胺 作用下， 以 正丁醇 为溶剂， 生成 (2R,3S,4R,5R,6S)-5-Amino-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
• 作为产物：
  描述：

  benzyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside 、 ethyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 MS 3 Angstroem 作用下， 以 乙腈 为溶剂， 以95%的产率得到Acetic acid (2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-((2S,3S,4S,5R,6R)-2,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester
  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