prop-2-enyl (2S,3R)-3-[(2S,3R,4R,5R,6R)-4-[(2S,4'S,4aS,5R,5'R,6'R,7R,8R,8aS)-5'-acetamido-3-oxo-4',8-bis(phenylmethoxy)-5-(phenylmethoxymethyl)-6'-[(1S,2R)-1,2,3-tris(phenylmethoxy)propyl]spiro[5,7,8,8a-tetrahydro-4aH-pyrano[3,4-b][1,4]dioxine-2,2'-oxane]-7-yl]oxy-3-azido-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)butanoate | 227286-37-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: prop-2-enyl (2S,3R)-3-[(2S,3R,4R,5R,6R)-4-[(2S,4'S,4aS,5R,5'R,6'R,7R,8R,8aS)-5'-acetamido-3-oxo-4',8-bis(phenylmethoxy)-5-(phenylmethoxymethyl)-6'-[(1S,2R)-1,2,3-tris(phenylmethoxy)propyl]spiro[5,7,8,8a-tetrahydro-4aH-pyrano[3,4-b][1,4]dioxine-2,2'-oxane]-7-yl]oxy-3-azido-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)butanoate
• CAS: 227286-37-5
• 化学式: C₈₇H₉₃N₅O₂₁
• 分子量: 1544.72
• InChiKey: GMPQOZKONRJYSS-URBACINWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.2
• 重原子数：
  113
• 可旋转键数：
  38
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  286
• 氢给体数：
  4
• 氢受体数：
  23

反应信息

• 作为反应物：
  描述：

  苯甲醛二甲缩醛 、 prop-2-enyl (2S,3R)-3-[(2S,3R,4R,5R,6R)-4-[(2S,4'S,4aS,5R,5'R,6'R,7R,8R,8aS)-5'-acetamido-3-oxo-4',8-bis(phenylmethoxy)-5-(phenylmethoxymethyl)-6'-[(1S,2R)-1,2,3-tris(phenylmethoxy)propyl]spiro[5,7,8,8a-tetrahydro-4aH-pyrano[3,4-b][1,4]dioxine-2,2'-oxane]-7-yl]oxy-3-azido-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)butanoate 在 对甲苯磺酸 作用下， 以 乙腈 为溶剂， 反应 0.25h， 以86%的产率得到N-(9-fluorenylmethoxycarbonyl)-O-[(5-acetamido-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->3)-(2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl-...]...
  参考文献：
  名称：

  带有连续唾液酸-T抗原的人糖蛋白AM的糖肽的固相合成。

  摘要：

  使用在弱酸不稳定的树脂上高效糖基化的氨基酸结构单元，可以完成带有连续唾液酸-T抗原的人糖蛋白AM的N端糖五肽的Fmoc固相合成。将苄基化的糖肽用TFA中的TMSOTf-硫代茴香醚处理，然后用NaHCO 3水溶液处理，以良好的产率提供脱保护的糖肽。

  DOI：

  10.1016/s0008-6215(00)00235-4
• 作为产物：
  描述：

  prop-2-enyl (2S,3R)-3-[(2S,3R,4R,5R,6R)-4-[(2S,4'S,4aS,5R,5'R,6'R,7R,8R,8aS)-5'-acetamido-3-oxo-4',8-bis(phenylmethoxy)-5-(phenylmethoxymethyl)-6'-[(1S,2R)-1,2,3-tris(phenylmethoxy)propyl]spiro[5,7,8,8a-tetrahydro-4aH-pyrano[3,4-b][1,4]dioxine-2,2'-oxane]-7-yl]oxy-3-azido-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-hydroxyoxan-2-yl]oxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)butanoate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到prop-2-enyl (2S,3R)-3-[(2S,3R,4R,5R,6R)-4-[(2S,4'S,4aS,5R,5'R,6'R,7R,8R,8aS)-5'-acetamido-3-oxo-4',8-bis(phenylmethoxy)-5-(phenylmethoxymethyl)-6'-[(1S,2R)-1,2,3-tris(phenylmethoxy)propyl]spiro[5,7,8,8a-tetrahydro-4aH-pyrano[3,4-b][1,4]dioxine-2,2'-oxane]-7-yl]oxy-3-azido-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)butanoate
  参考文献：
  名称：

  The first total synthesis of the core class II disialylated hexasaccharide as a building block for glycopeptide synthesis

  摘要：

  The first total synthesis of the protected core class II sialylated glycosyl-Thr hexasaccharide (3), utilizing suitably protected building blocks 4, 5, 7 and 8 was accomplished. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00605-x

文献信息

• Solid-phase synthesis of the glycopeptide of human glycophorin AM bearing the consecutive sialyl-T antigen
  作者：Sumie Ando、Yuko Nakahara、Yukishige Ito、Tomoya Ogawa、Yoshiaki Nakahara

  DOI：10.1016/s0008-6215(00)00235-4

  日期：2000.12

  Fmoc solid-phase synthesis of the N-terminal glycopentapeptide of human glycophorin AM, bearing the consecutive sialyl-T antigen, was accomplished using glycosylated amino acid building blocks on a weakly acid-labile resin with high efficiency. The benzylated glycopeptide was treated with TMSOTf-thioanisole in TFA and then with aq NaHCO3 to afford the deprotected glycopeptide in good yield.

  使用在弱酸不稳定的树脂上高效糖基化的氨基酸结构单元，可以完成带有连续唾液酸-T抗原的人糖蛋白AM的N端糖五肽的Fmoc固相合成。将苄基化的糖肽用TFA中的TMSOTf-硫代茴香醚处理，然后用NaHCO 3水溶液处理，以良好的产率提供脱保护的糖肽。
• The first total synthesis of the core class II disialylated hexasaccharide as a building block for glycopeptide synthesis
  作者：Latika Singh、Yuko Nakahara、Yukishige Ito、Yoshiaki Nakahara

  DOI：10.1016/s0040-4039(99)00605-x

  日期：1999.5

  The first total synthesis of the protected core class II sialylated glycosyl-Thr hexasaccharide (3), utilizing suitably protected building blocks 4, 5, 7 and 8 was accomplished. (C) 1999 Elsevier Science Ltd. All rights reserved.