2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-β-D-glucopyranosyl fluoride | 149300-00-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-β-D-glucopyranosyl fluoride
• CAS: 149300-00-5
• 化学式: C₆₁H₆₃FO₁₀
• 分子量: 975.164
• InChiKey: OZAZEKZMSIQRJB-QHXLLDNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.15
• 重原子数：
  72.0
• 可旋转键数：
  25.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  92.3
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-((2R,4aS,6R,7R,8R,8aS)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[2,3-b][1,4]dioxin-6-yloxy)-tetrahydro-pyran-3-ol 、 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-β-D-glucopyranosyl fluoride 在 三氟甲磺酸酐 、 4 A molecular sieve 作用下， 以 乙醚 为溶剂， 反应 50.0h， 以58%的产率得到O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->4)-O-(2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->4)-O-(2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside
  参考文献：
  名称：

  All-α-d-linked tetra- and penta-saccharide substructures of Trestatin A by block syntheses with triflic anhydride as promoter

  摘要：

  The perbenzylated maltosyl and maltotriosyl fluorides 6 and 16 were treated with 2,3,2',3',6'-penta-O-benzyl-4,6-O-benzylidene-alpha,alpha-trehalose (7) using triflic anhydride as a promoter to give all-alpha-D-linked tetra- and penta-saccharides which were finally deblocked to the free oligosaccharides 4-O-alpha-maltosyl- 9 and 4-O-alpha-maltotriosyl-alpha,alpha-trehaloses 18. The H-1 NMR spectra of some of the compounds were fully analyzed by 1D TOCSY and ROESY experiments.

  DOI：

  10.1016/0008-6215(93)80028-d
• 作为产物：
  描述：

  2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-α-D-glucopyranosyl chloride 在 silver fluoride 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以69%的产率得到2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-β-D-glucopyranosyl fluoride
  参考文献：
  名称：

  All-α-d-linked tetra- and penta-saccharide substructures of Trestatin A by block syntheses with triflic anhydride as promoter

  摘要：

  The perbenzylated maltosyl and maltotriosyl fluorides 6 and 16 were treated with 2,3,2',3',6'-penta-O-benzyl-4,6-O-benzylidene-alpha,alpha-trehalose (7) using triflic anhydride as a promoter to give all-alpha-D-linked tetra- and penta-saccharides which were finally deblocked to the free oligosaccharides 4-O-alpha-maltosyl- 9 and 4-O-alpha-maltotriosyl-alpha,alpha-trehaloses 18. The H-1 NMR spectra of some of the compounds were fully analyzed by 1D TOCSY and ROESY experiments.

  DOI：

  10.1016/0008-6215(93)80028-d

文献信息

• Chemical synthesis and NMR spectra of a protected branched-tetrasaccharide thioglycoside, a useful intermediate for the synthesis of branched oligosaccharides
  作者：Mohammed Saddik Motawia、Carl Erik Olsen、Birger Lindberg Møller、Jan Marcussen

  DOI：10.1016/0008-6215(94)90006-x

  日期：1994.1

  6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl- alpha-D-glucopyranosyl) -alpha,beta-D-glucopyranosyl trichloroacetimidate (9), which was effectively used as the glycosyl donor in the condensation reaction with compound 4, using trimethylsilyl triflate as catalyst, to obtain the branched tetrasaccharides phenyl O-[2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranosyl)- (1-->4)]-O-(2,3,6-tri-O-benzyl-alpha-D-glucopyranosyl)-(1-->6)-O-(2

  过O-乙酰化的1,6-脱水麦芽糖（3）的酸催化硫酚反应生成苯基2,3-二-O-乙酰基-4-O-（2,3,4,6-四-O-乙酰基-α -D-吡喃葡萄糖基）-1-硫代β-D-吡喃葡萄糖苷（4）的定量产率。苯基4-O-α-D-吡喃葡糖基-1-硫代-β-D-吡喃葡糖苷（5）是通过使用三甲基甲硅烷基三氟甲磺酸酯作为催化剂，通过酸催化麦芽糖八乙酸酯（2）的硫酚基化而得到的。5的标准苄基化反应生成苯基2,3-二-O-苄基-4-O-（2,3,4,6-四-O-苄基-α-D-吡喃葡萄糖基）-1-硫代-β-D-葡萄糖苷（6），在丙酮水溶液中用N-溴琥珀酰亚胺处理后，得到2,3,6-三-O-苄基-4-O-（2,3,4,6-四-O-苄基-α- D-吡喃葡萄糖基）-D-吡喃葡萄糖（8）。在无水碳酸钾存在下，用三氯乙腈处理化合物8，得到2,3，完整的NMR解释为10。研究了支链四糖合成的替代方法。苯基硫代糖苷5的化学合