N-(9-fluorenylmethoxycarbonyl)-O-[2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl-(1->3)-2-azido-2-deoxy-α-D-galactopyranosyl]-L-threonine allyl ester | 931104-00-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(9-fluorenylmethoxycarbonyl)-O-[2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl-(1->3)-2-azido-2-deoxy-α-D-galactopyranosyl]-L-threonine allyl ester
• 英文别名: prop-2-enyl (2S,3R)-3-[(2S,3R,4R,5R,6R)-3-azido-5-hydroxy-6-(hydroxymethyl)-4-[(2R,3R,4R,5S,6R)-4-phenylmethoxy-6-(phenylmethoxymethyl)-3-[(2,2,2-trichloroacetyl)amino]-5-[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxan-2-yl]oxyoxan-2-yl]oxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)butanoate
• CAS: 931104-00-6
• 化学式: C₈₄H₈₈Cl₃N₅O₁₉
• 分子量: 1578.0
• InChiKey: FJSTXXIFMANOBB-POJSPFOESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.1
• 重原子数：
  111
• 可旋转键数：
  38
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  259
• 氢给体数：
  4
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  N-[(2R,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((4aR,6S,7R,8S,8aS)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-2-fluoro-tetrahydro-pyran-3-yl]-2,2,2-trichloro-acetamide 、 N-(9-fluorenylmethoxycarbonyl)-O-[2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl-(1->3)-2-azido-2-deoxy-α-D-galactopyranosyl]-L-threonine allyl ester 在 二氯二茂锆 silver perchlorate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以71%的产率得到N-[(2R,3R,4R,5S,6R)-5-[[(4aR,6S,7R,8S,8aS)-2-phenyl-7,8-bis(phenylmethoxy)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-2-[[(2R,3R,4R,5R,6S)-5-azido-6-[(2R,3S)-3-[[9H-fluoren-9-ylmethoxy(hydroxy)methylidene]amino]-4-oxo-4-prop-2-enoxybutan-2-yl]oxy-3-hydroxy-4-[(2R,3R,4R,5S,6R)-4-phenylmethoxy-6-(phenylmethoxymethyl)-3-[(2,2,2-trichloro-1-hydroxyethylidene)amino]-5-[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxan-2-yl]oxyoxan-2-yl]methoxy]-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl]-2,2,2-trichloroethanimidic acid
  参考文献：
  名称：

  Synthesis of biantennary LacNAc-linked O-glycan (core 4) and glycopeptide thioester by benzyl protection strategy: rapid zinc reduction of GlcNTCA to GlcNAc by microwave irradiation

  摘要：

  A synthetic method for the core 4 O-glycan-linked Ser and Thr was developed. Highly stereoselective 3-O- and 6-O-glycosylation was achieved by using two distinctively protected N-trichloroacetyllactosaminyl fluorides (3 and 12). Microwave-assisted Zn reduction rapidly and efficiently converted N-trichloroacetylglucosamine (GlcNTCA) to N-acetylglucosamine (GlcNAc). In order to demonstrate the usefulness of the protected core 4 O-glycan a segment (Gly(34)-Gly(58)) of emmprin (extracellular matrix metalloproteinase inducer), a cancer metastasis-related glycoprotein, was synthesized by the solid-phase method, utilizing the pentasaccharyl Thr (2) to introduce an O-glycan in place of the native N-glycan at Asn(44). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.12.088
• 作为产物：
  描述：

  N-(9-fluorenylmethoxycarbonyl)-O-[2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl]-L-threonine allyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到N-(9-fluorenylmethoxycarbonyl)-O-[2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl-(1->3)-2-azido-2-deoxy-α-D-galactopyranosyl]-L-threonine allyl ester
  参考文献：
  名称：

  Synthesis of biantennary LacNAc-linked O-glycan (core 4) and glycopeptide thioester by benzyl protection strategy: rapid zinc reduction of GlcNTCA to GlcNAc by microwave irradiation

  摘要：

  A synthetic method for the core 4 O-glycan-linked Ser and Thr was developed. Highly stereoselective 3-O- and 6-O-glycosylation was achieved by using two distinctively protected N-trichloroacetyllactosaminyl fluorides (3 and 12). Microwave-assisted Zn reduction rapidly and efficiently converted N-trichloroacetylglucosamine (GlcNTCA) to N-acetylglucosamine (GlcNAc). In order to demonstrate the usefulness of the protected core 4 O-glycan a segment (Gly(34)-Gly(58)) of emmprin (extracellular matrix metalloproteinase inducer), a cancer metastasis-related glycoprotein, was synthesized by the solid-phase method, utilizing the pentasaccharyl Thr (2) to introduce an O-glycan in place of the native N-glycan at Asn(44). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.12.088