4'-acetamido-2,3,4,6,1',3',6'-hepta-O-acetyl-4'-deoxysucrose | 111829-06-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4'-acetamido-2,3,4,6,1',3',6'-hepta-O-acetyl-4'-deoxysucrose
• CAS: 111829-06-2
• 化学式: C₂₈H₃₉NO₁₈
• 分子量: 677.614
• InChiKey: RWYOXZUFIDEPSL-SAXBRCJISA-N

反应信息

• 作为产物：
  描述：

  乙酸酐 、 (2R,3R,4S,5S,6R)-2-((2S,3S,4S,5S)-4-Amino-3-hydroxy-2,5-bis-hydroxymethyl-tetrahydro-furan-2-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 以 吡啶 为溶剂， 反应 16.0h， 生成 4'-acetamido-2,3,4,6,1',3',6'-hepta-O-acetyl-4'-deoxysucrose
  参考文献：
  名称：

  Ring-opening reactions of sucrose epoxides: Synthesis of 4′-derivatives of sucrose

  摘要：

  The 2,1''-O-isopropylidene derivative (1) of 3-O-acetyl-4,6-O-isopropylidene-.alpha.-D-glucopyranosyl 6-O-acetyl-3,4-anhydro-.beta.-D-lyxo-hexulofuranoside and 2,3,4-tri-O-acetyl-6-O-trityl-.alpha.-D-glucopyranosyl 3,4-anhydro-1,6-di-O-trityl-.beta.-D-lyxo-hexulofuranoside have been synthesised and 1 has been converted into 2,3,4,6-tetra-O-acetyl-.alpha.-D-glucopyranosyl 1,6-di-O-acetyl-3,4-anhydro-.beta.-D-lyxo-hexulofuranoside (2). The SN2 reactions of 2 with azide and chloride nucleophiles gave the corresponding 2,3,4,6-tetra-O-acetyl-.alpha.-D-glucopyranosyl 1,3,6-tri-O-acetyl-4-azido-4-deoxy-.beta.-D-fructofuranoside (6) and 2,3,4,6-tetra-O-acetyl-.alpha.-D-glucopyranosyl 1,3,6-tri-O-acetyl-4-chloro-4-deoxy-.beta.-D-fructofuranoside (8), respectively. The azide 6 was catalytically hydrogenated and the resulting amine was isolated as 2,3,4,6-tetra-O-acetyl-.alpha.-D-glucopyranosyl 4-acetamido-1,3,6-tri-O-acetyl-4-deoxy-.beta.-D-fructofuranoside. Treatment of 5 with hydrogen bromide in glacial acetic acid followed by conventional acetylation gave 2,3,4,6-tetra-O-acetyl-.alpha.-D-glucopyranosyl 1,3,6-tri-O-acetyl-4-bromo-4-deoxy-.beta.-D-fructofuranoside. Similar SN2 reactions with 2,3,4,6-tetra-O-acetyl-.alpha.-D-glucopyranosyl 1,6-di-O-acetyl-3,4-anhydro-.beta.-D-ribo-hexulofuranoside (12) resulted in a number of 4''-derivatives of .alpha.-D-glucopyranosyl .beta.-D-sorbofuranoside. The regiospecific nucleophilic substitution at position 4'' in 2 and 12 has been explained on the basis of steric and polar factors.

  DOI：

  10.1016/0008-6215(87)80215-x