[(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[(2R,3S,4R,5R,6S)-5-(1,3-dioxoisoindol-2-yl)-4-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-2-(phenylmethoxymethyl)-6-phenylsulfanyloxan-3-yl]oxyoxan-2-yl]methyl 2,2-dimethylpropanoate | 191331-62-1

• 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)-3,4,5-triacetyloxy-6-[(2R,3S,4R,5R,6S)-5-(1,3-dioxoisoindol-2-yl)-4-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-2-(phenylmethoxymethyl)-6-phenylsulfanyloxan-3-yl]oxyoxan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 191331-62-1
• 化学式: C₇₁H₇₇NO₁₉S
• 分子量: 1280.45
• InChiKey: QDCYPHDDZFUNBF-LPQYGGSOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  92
• 可旋转键数：
  30
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  251
• 氢给体数：
  0
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[(2R,3S,4R,5R,6S)-5-(1,3-dioxoisoindol-2-yl)-4-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-2-(phenylmethoxymethyl)-6-phenylsulfanyloxan-3-yl]oxyoxan-2-yl]methyl 2,2-dimethylpropanoate 在 camphor-10-sulfonic acid 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 [(3aS,4R,6S,7R,7aR)-6-[(2R,3S,4R,5R,6S)-5-(1,3-dioxoisoindol-2-yl)-4-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-2-(phenylmethoxymethyl)-6-phenylsulfanyloxan-3-yl]oxy-7-hydroxy-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]methyl 2,2-dimethylpropanoate
  参考文献：
  名称：

  First total synthesis of sialylated and sulfated Lewisx mucin Core 2 structures as potential tumor associated antigens

  摘要：

  Two branched Core 2 structures, (3-O-SO3Na)Gal beta 1-->4(Fuc alpha 1-->3)GlcNAc beta 1-->6(NeuAc alpha 2-->3Gal beta 1-->3)GalNAc alpha OMe (1) and its positional isomer NeuAc alpha 2-->3Gal beta 1-->4(Fuc alpha 1-->3)GlcNAc beta 1--> 6(3-OSO3Na-Gal beta 1-->3)GalNAc alpha OMe (2), were chemically synthesized for the first time as potential tumor associated antigens. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00975-8
• 作为产物：
  描述：

  phenyl 6-O-benzyl-2-deoxy-2-phthalimido-1-thio-1-deoxy-β-D-glucopyranoside 在 四丁基溴化铵 、 silver trifluoromethanesulfonate 、 tin(ll) chloride 、 copper(ll) bromide 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 20.0h， 生成 [(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[(2R,3S,4R,5R,6S)-5-(1,3-dioxoisoindol-2-yl)-4-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-2-(phenylmethoxymethyl)-6-phenylsulfanyloxan-3-yl]oxyoxan-2-yl]methyl 2,2-dimethylpropanoate
  参考文献：
  名称：

  Synthesis of sulfo and sialyl LewisX analogs with a mannose at the reducing end

  摘要：

  Stereoselective syntheses of 3-O-sulfo and 3-O-sialyl Lewis(X) analogs 1 and 2 were accomplished. Compound 1 showed greater inhibitory activity than the natural ligand sialyl Lewis(X) against P and L-selectin.

  DOI：

  10.1016/s0960-894x(97)00181-9