[(2S,4'S,4aS,5R,5'R,6'R,7S,8R,8aS)-5'-acetamido-4'-acetyloxy-5-(acetyloxymethyl)-7-ethylsulfanyl-3-oxo-6'-[(1S,2R)-1,2,3-triacetyloxypropyl]spiro[5,7,8,8a-tetrahydro-4aH-pyrano[3,4-b][1,4]dioxine-2,2'-oxane]-8-yl] benzoate | 215028-96-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2S,4'S,4aS,5R,5'R,6'R,7S,8R,8aS)-5'-acetamido-4'-acetyloxy-5-(acetyloxymethyl)-7-ethylsulfanyl-3-oxo-6'-[(1S,2R)-1,2,3-triacetyloxypropyl]spiro[5,7,8,8a-tetrahydro-4aH-pyrano[3,4-b][1,4]dioxine-2,2'-oxane]-8-yl] benzoate
• CAS: 215028-96-9
• 化学式: C₃₆H₄₅NO₁₈S
• 分子量: 811.815
• InChiKey: WMLKMKTYEMQLDQ-KUVYDHCQSA-N

物化性质

• 沸点：
  861.006±65.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.395±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  56
• 可旋转键数：
  20
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  266
• 氢给体数：
  1
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  [(2S,4'S,4aS,5R,5'R,6'R,7S,8R,8aS)-5'-acetamido-4'-acetyloxy-5-(acetyloxymethyl)-7-ethylsulfanyl-3-oxo-6'-[(1S,2R)-1,2,3-triacetyloxypropyl]spiro[5,7,8,8a-tetrahydro-4aH-pyrano[3,4-b][1,4]dioxine-2,2'-oxane]-8-yl] benzoate 、 methyl (2R,4S,5R,6R)-5-acetamido-4-acetyloxy-2-[[(2R,3R,4R,5R,6S)-5-azido-6-[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-oxo-3-phenylmethoxypropoxy]-3,4-dihydroxyoxan-2-yl]methoxy]-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 0.08h， 以53%的产率得到methyl (2R,4S,5R,6R)-2-[[(2R,3R,4R,5R,6S)-4-[(2S,4'S,4aS,5R,5'R,6'R,7R,8R,8aS)-5'-acetamido-4'-acetyloxy-5-(acetyloxymethyl)-8-benzoyloxy-3-oxo-6'-[(1S,2R)-1,2,3-triacetyloxypropyl]spiro[5,7,8,8a-tetrahydro-4aH-pyrano[3,4-b][1,4]dioxine-2,2'-oxane]-7-yl]oxy-5-azido-6-[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-oxo-3-phenylmethoxypropoxy]-3-hydroxyoxan-2-yl]methoxy]-5-acetamido-4-acetyloxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
  参考文献：
  名称：

  A Broadly Applicable Method for the Efficient Synthesis of α-O-Linked Glycopeptides and Clustered Sialic Acid Residues

  摘要：

  The total syntheses of complex sialylated cell-surface antigens have been accomplished. The target systems include 2.3-STF, STn, 2,6-STF, and glycophorin antigens. In addition,an alpha-O-linked serine glycoside of an entire Lewis blood group (Y) antigen has been assembled.

  DOI：

  10.1021/ja9833265
• 作为产物：
  描述：

  N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester 在 4-二甲氨基吡啶 、 二叔丁基过氧化物 、 四丁基氟化铵 、 silver trifluoromethanesulfonate 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 45.0h， 生成 [(2S,4'S,4aS,5R,5'R,6'R,7S,8R,8aS)-5'-acetamido-4'-acetyloxy-5-(acetyloxymethyl)-7-ethylsulfanyl-3-oxo-6'-[(1S,2R)-1,2,3-triacetyloxypropyl]spiro[5,7,8,8a-tetrahydro-4aH-pyrano[3,4-b][1,4]dioxine-2,2'-oxane]-8-yl] benzoate
  参考文献：
  名称：

  A Broadly Applicable Method for the Efficient Synthesis of α-O-Linked Glycopeptides and Clustered Sialic Acid Residues

  摘要：

  The total syntheses of complex sialylated cell-surface antigens have been accomplished. The target systems include 2.3-STF, STn, 2,6-STF, and glycophorin antigens. In addition,an alpha-O-linked serine glycoside of an entire Lewis blood group (Y) antigen has been assembled.

  DOI：

  10.1021/ja9833265