4-O-(4-O-acetyl-2,3,6-trideoxy-2-iodo-α-L-arabino-hexopyranosyl)-1,5-anhydro-3-O-benzyl-2,6-dideoxy-L-lyxo-hex-1-enitol | 136933-31-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-O-(4-O-acetyl-2,3,6-trideoxy-2-iodo-α-L-arabino-hexopyranosyl)-1,5-anhydro-3-O-benzyl-2,6-dideoxy-L-lyxo-hex-1-enitol
• 英文别名: [(2S,3R,5R,6S)-5-iodo-2-methyl-6-[[(2S,3R,4S)-2-methyl-4-phenylmethoxy-3,4-dihydro-2H-pyran-3-yl]oxy]oxan-3-yl] acetate
• CAS: 136933-31-8
• 化学式: C₂₁H₂₇IO₆
• 分子量: 502.346
• InChiKey: QLLUZXVAXHDEBH-PYGYSWEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  benzyl 3-azido-2,3,6-trideoxy-α-L-threo-hex-2-enopyranoside 、 4-O-(4-O-acetyl-2,3,6-trideoxy-2-iodo-α-L-arabino-hexopyranosyl)-1,5-anhydro-3-O-benzyl-2,6-dideoxy-L-lyxo-hex-1-enitol 在 N-碘代丁二酰亚胺 、 4 A molecular sieve 作用下， 以 乙腈 为溶剂， 反应 168.0h， 以27%的产率得到benzyl 4-O-<(4-O-acetyl-2,3,6-trideoxy-2-iodo-α-L-arabino-hexopyranosyl)-3-O-benzyl-2,6-dideoxy-2-iodo-α-L-talo-hexopyranosyl>-3-azido-2,3,6-trideoxy-α-L-threo-hex-2-enopyranoside
  参考文献：
  名称：

  Approaches to the C-B-A trisaccharide of dihydroaclacinomycin by extending the chain from either side

  摘要：

  Selective benzylation of L-fucal (1) under phase-transfer conditions gave the 3- and 4-monoethers 2 and 3, respectively. Two routes, the "tail" or the "head" addition are presented, both leading to the target molecule 9, a mimic of the C-B-A trisaccharide component of dihydroaclacinomycin. Addition of glycals 2 and 3 respectively, to the acetylated glycal (7) of amicetose used as glycosyl donor gave the disaccharide glycals 6 and 8. Alternatively, glucosylation of the 4-acetate (4) of 2 with the benzyl hex-2-enopyranoside derivative 10 gave the disaccharide derivative 11. In the first case, the final glycosylation step involves the addition of 10 to disaccharide glycal 8. In the second procedure, the disaccharide alcohol 12 is obtained by O-deacetylation of 11, and serves as the glycosyl acceptor for glycal derivative 7 to give the C-B-a precursor trisaccharide derivative.

  DOI：

  10.1016/0008-6215(92)84182-r
• 作为产物：
  描述：

  L-fucal 在 氢氧化钾 、 N-碘代丁二酰亚胺 、 4 A molecular sieve 、 四丁基溴化铵 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 48.0h， 生成 4-O-(4-O-acetyl-2,3,6-trideoxy-2-iodo-α-L-arabino-hexopyranosyl)-1,5-anhydro-3-O-benzyl-2,6-dideoxy-L-lyxo-hex-1-enitol
  参考文献：
  名称：

  Approaches to the C-B-A trisaccharide of dihydroaclacinomycin by extending the chain from either side

  摘要：

  Selective benzylation of L-fucal (1) under phase-transfer conditions gave the 3- and 4-monoethers 2 and 3, respectively. Two routes, the "tail" or the "head" addition are presented, both leading to the target molecule 9, a mimic of the C-B-A trisaccharide component of dihydroaclacinomycin. Addition of glycals 2 and 3 respectively, to the acetylated glycal (7) of amicetose used as glycosyl donor gave the disaccharide glycals 6 and 8. Alternatively, glucosylation of the 4-acetate (4) of 2 with the benzyl hex-2-enopyranoside derivative 10 gave the disaccharide derivative 11. In the first case, the final glycosylation step involves the addition of 10 to disaccharide glycal 8. In the second procedure, the disaccharide alcohol 12 is obtained by O-deacetylation of 11, and serves as the glycosyl acceptor for glycal derivative 7 to give the C-B-a precursor trisaccharide derivative.

  DOI：

  10.1016/0008-6215(92)84182-r