N-((2S,4S,4a'S,5R,5'R,6R,7'S,8'R,8a'S)-4,8'-bis(benzyloxy)-5'-((benzyloxy)methyl)-7'-(4-methoxyphenoxy)-3'-oxo-6-((1S,2R)-1,2,3-tris(benzyloxy)propyl)octahydro-3'H,5'H-spiro[pyran-2,2'-pyrano[3,4-b][1,4]dioxin]-5-yl)acetamide | 159922-53-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-((2S,4S,4a'S,5R,5'R,6R,7'S,8'R,8a'S)-4,8'-bis(benzyloxy)-5'-((benzyloxy)methyl)-7'-(4-methoxyphenoxy)-3'-oxo-6-((1S,2R)-1,2,3-tris(benzyloxy)propyl)octahydro-3'H,5'H-spiro[pyran-2,2'-pyrano[3,4-b][1,4]dioxin]-5-yl)acetamide
• CAS: 159922-53-9
• 化学式: C₆₆H₆₉NO₁₄
• 分子量: 1100.27
• InChiKey: LDZFBGJCGVEDJH-MZWQRGSBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.87
• 重原子数：
  81.0
• 可旋转键数：
  26.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  156.93
• 氢给体数：
  1.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  N-((2S,4S,4a'S,5R,5'R,6R,7'S,8'R,8a'S)-4,8'-bis(benzyloxy)-5'-((benzyloxy)methyl)-7'-(4-methoxyphenoxy)-3'-oxo-6-((1S,2R)-1,2,3-tris(benzyloxy)propyl)octahydro-3'H,5'H-spiro[pyran-2,2'-pyrano[3,4-b][1,4]dioxin]-5-yl)acetamide 在 ammonium cerium(IV) nitrate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 水 、 甲苯 、 乙腈 为溶剂， 生成 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-α,β-D-galactopyranosyl trichloroacetimidate-(1b->4a)-lactone
  参考文献：
  名称：

  Total synthesis of B-chain of human α2HS glycoprotein

  摘要：

  B-chain of human alpha 2HS glycoprotein 1, a cystein-containing heptacosapeptide carrying a trisaccharide (sialyl T) side chain, was synthesized for the first time by the solid-phase method utilizing a glycosyl serine building block 11 with benzyl protecting groups. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01718-8
• 作为产物：
  描述：

  4-甲氧苯基2,6-二-O-苄基-3,4-O-异亚丙基-β-D-吡喃半乳糖苷 在 偶氮二异丁腈 、 mercury salt 、 三苯基氢化锡 、 水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 8.0h， 生成 N-((2S,4S,4a'S,5R,5'R,6R,7'S,8'R,8a'S)-4,8'-bis(benzyloxy)-5'-((benzyloxy)methyl)-7'-(4-methoxyphenoxy)-3'-oxo-6-((1S,2R)-1,2,3-tris(benzyloxy)propyl)octahydro-3'H,5'H-spiro[pyran-2,2'-pyrano[3,4-b][1,4]dioxin]-5-yl)acetamide
  参考文献：
  名称：

  Synthesis of human M blood group antigenic glycopeptide

  摘要：

  A first total synthesis of N-terminal glycoheptapeptide of human glycophorin AM was accomplished by solution phase peptide condensation utilizing the tetrasaccharide-linked amino acid building blocks designed for Fmoc strategy.

  DOI：

  10.1016/s0040-4039(00)76897-3

文献信息

• Solid-phase synthesis of the B-chain of human α2HS glycoprotein
  作者：Yoshiaki Nakahara、Yuko Nakahara、Yukishige Ito、Tomoya Ogawa

  DOI：10.1016/s0008-6215(98)00142-6

  日期：1998.7

  The B-chain of human alpha 2HS glycoprotein 1, a heptacosapeptide carrying a trisaccharide (sialyl T) side chain, was synthesized. Prior to the Fmoc-based solid-phase synthesis of the glycopeptide, the benzyl-protected glycosyl serine building block 6 was prepared via beta-stereoselective glycosylation of the 2-azido-2-deoxygalactosyl serine 11 with the sialyl galactosyl trichloroacetimidate 9. An automated peptide synthesizer was efficiently used for the elongation of the entire peptide chain except for the coupling with 6. The synthesized glycopeptide was cleaved from the resin by the TFA method. The resultant mixture of the benzylated glycopeptides was treated with TMSOTf-thioanisole in TFA and then with aq NaHCO3 and 1,4-dithiothreitol to give 1. (C) 1998 Elsevier Science Ltd. All rights reserved.