(S)-3-[(2S,3R,4R,5R,6R)-3-Azido-6-(tert-butyl-dimethyl-silanyloxymethyl)-4,5-dihydroxy-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid allyl ester | 197630-87-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-3-[(2S,3R,4R,5R,6R)-3-Azido-6-(tert-butyl-dimethyl-silanyloxymethyl)-4,5-dihydroxy-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid allyl ester
• CAS: 197630-87-8
• 化学式: C₃₃H₄₄N₄O₉Si
• 分子量: 668.819
• InChiKey: PDYUPDNPQFJDGQ-VOZJJELXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.79
• 重原子数：
  47.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  181.54
• 氢给体数：
  3.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (S)-3-[(2S,3R,4R,5R,6R)-3-Azido-6-(tert-butyl-dimethyl-silanyloxymethyl)-4,5-dihydroxy-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid allyl ester 、 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 在 三氟化硼乙醚 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 以7%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-nanulopyranosylonic acid]-(2->3)-(2,6-di-O-benzyl-α-D-galactopyranosyl)-(1->3)-2-azido-6-O-tert-butyldimethylsilyl-2-deoxy-α-D-galactopyranos...
  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：

  allyl N-(9-fluorenylmethoxycarbonyl)-[O-(2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-(1[*]3)]-L-serine 在 咪唑 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 (S)-3-[(2S,3R,4R,5R,6R)-3-Azido-6-(tert-butyl-dimethyl-silanyloxymethyl)-4,5-dihydroxy-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid allyl ester
  参考文献：
  名称：

  Solid-phase synthesis of the B-chain of human α2HS glycoprotein

  摘要：

  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.

  DOI：

  10.1016/s0008-6215(98)00142-6