3,6-di-O-benzyl-4-O-(3',6'-di-O-allyl-2',4'-di-O-benzyl-D-mannopyranosyl)-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride | 174060-48-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,6-di-O-benzyl-4-O-(3',6'-di-O-allyl-2',4'-di-O-benzyl-D-mannopyranosyl)-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride
• 英文别名: 2-[(2S,3R,4R,5S,6R)-5-[(2S,3S,4S,5R,6R)-3,5-bis(phenylmethoxy)-4-prop-2-enoxy-6-(prop-2-enoxymethyl)oxan-2-yl]oxy-2-fluoro-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl]isoindole-1,3-dione
• CAS: 174060-48-1
• 化学式: C₅₄H₅₆FNO₁₁
• 分子量: 914.037
• InChiKey: VDQRPVSLIYWHCT-IUXAPPFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  67
• 可旋转键数：
  23
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  120
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide 、 3,6-di-O-benzyl-4-O-(3',6'-di-O-allyl-2',4'-di-O-benzyl-D-mannopyranosyl)-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride 在 二氯二茂铪 、 4 A molecular sieve 、 silver perchlorate 作用下， 生成 3,6-di-O-benzyl-4-O-[3',6'-di-O-benzyl-4'-O-(3'',6''-di-O-allyl-2'',4''-di-O-benzyl-D-mannopyranosyl)-2'-deoxy-2'-phthalimido-β-D-glucopyranosyl]-2-deoxy-2-phthalimido-β-D-glucopyranosyl azido
  参考文献：
  名称：

  Solid-phase synthesis of CD52 glycopeptide and an efficient route to Asn-core pentasaccharide conjugate

  摘要：

  The intact peptide sequence (18) as well as its glycoform carrying an N-linked core pentasaccharide (I) of CD52 antigen were prepared by means of solid-phase synthesis employing Fmoc-amino acids and benzyl-protected oligo saccharide-asparagine conjugate (3) as building blocks. It was concluded that the pentasaccharide structure had little influence on further peptide elongation in solid-phase synthesis and the benzylated pentasaccharide moiety was sufficiently stable to the 95% TFA acidic conditions used to release glycopeptide from the supporting resin. The paper also describes an efficient route leading to asparagine-core pentasaccharide conjugate (3) which was prepared in seven steps for an overall yield of 23% from monosaccharide units 5, 6, 7 and 8. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00126-0
• 作为产物：
  描述：

  3,6-di-O-allyl-2,4-di-O-benzyl-D-mannopyranose 在 tetrakis(pentafluorophenyl)boric acid 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 1.2h， 生成 3,6-di-O-benzyl-4-O-(3',6'-di-O-allyl-2',4'-di-O-benzyl-D-mannopyranosyl)-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride
  参考文献：
  名称：

  6-Nitro-2-benzothiazolyl α-Mannoside: 构建 β-Man(1→4)GlcN 键的高效甘露糖供体及其在 N-聚糖五糖核心合成中的应用

  摘要：

  已经建立了存在于 N-连接聚糖中的 β-Man(1→4)GlcN 键的高效简明合成。葡萄糖胺衍生物的 4-OH 基团的直接 β-甘露糖基化...

  DOI：

  10.1246/bcsj.79.479

文献信息

• Efficient and Concise Synthesis of βMan1–4GlcN Linkage of Pentasaccharide Core by Using 6-Nitro-2-benzothiazolyl α-Mannoside
  作者：Hiroki Mandai、Teruaki Mukaiyama

  DOI：10.1246/cl.2005.702

  日期：2005.5

  Efficient and concise synthesis of βMan1–4GlcN of pentasaccharide core is established; direct β-mannosylations of 4-OH group of 2-deoxy-2-phthaloyl and 2-azide-2-deoxy glucose derivatives by using 6-nitro-2-benzothiazolyl α-mannoside proceeded smoothly to afford the desired β-mannosides in high yields.

  利用 6-硝基-2-苯并噻唑基 α-甘露糖苷对 2-脱氧-2-邻苯二甲酰和 2-叠氮-2-脱氧葡萄糖衍生物的 4-OH基团进行直接 β-甘露糖苷化，顺利合成了五糖核心的 βMan1-4GlcN ，并获得了高产率的所需 β-甘露糖苷。