3-aminopropyl 6-deoxy-2-O-<3-O-<2-O-methyl-(4-O-methyl-α-L-rhamnopyranosyl)-α-L-fucopyranosyl>-α-L-rhamnopyranosyl>-α-L-talopyranoside | 148404-60-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-aminopropyl 6-deoxy-2-O-<3-O-<2-O-methyl-(4-O-methyl-α-L-rhamnopyranosyl)-α-L-fucopyranosyl>-α-L-rhamnopyranosyl>-α-L-talopyranoside
• 英文别名: 3NP-Mmrfrt；(2S,3S,4R,5R,6R)-6-(3-aminopropoxy)-5-[(2S,3R,4R,5S,6S)-4-[(2S,3S,4R,5S,6S)-5-[(2S,3R,4S,5R,6S)-3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl]oxy-4-hydroxy-3-methoxy-6-methyloxan-2-yl]oxy-3,5-dihydroxy-6-methyloxan-2-yl]oxy-2-methyloxane-3,4-diol
• CAS: 148404-60-8
• 化学式: C₂₉H₅₃NO₁₇
• 分子量: 687.736
• InChiKey: DMCKJTFEHYELGM-DDOBRSFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.3
• 重原子数：
  47
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  260
• 氢给体数：
  8
• 氢受体数：
  18

反应信息

• 作为产物：
  描述：

  在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 水 、 异丙醇 为溶剂， 反应 48.0h， 生成 3-aminopropyl 6-deoxy-2-O-<3-O-<2-O-methyl-(4-O-methyl-α-L-rhamnopyranosyl)-α-L-fucopyranosyl>-α-L-rhamnopyranosyl>-α-L-talopyranoside
  参考文献：
  名称：

  Iodonium ion-assisted synthesis of a haptenic tetrasaccharide fragment corresponding to the inner cell-wall glycopeptidolipid of Mycobacterium avium serotype 4

  摘要：

  Condensation of ethyl 2,4-di-O-benzoyl-1-thio-alpha-L-rhamnopyranoside with ethyl 3-O-benzyl-4-O-chloroacetyl-2-O-methyl-1-thio-beta-L-fucopyranoside in the presence of iodonium di-sym-collidine perchlorate afforded exclusively ethyl 2,4-di-O-benzoyl-3-O-(3-O-benzyl-4-O-chloroacetyl-2-O-methyl-alpha-L-fucopyranosyl)-1-thio-alpha-L-rhamnopyranoside. This disaccharide derivative was extended at C-1 with 3-benzyloxycarbonylaminopropyl 6-deoxy-3,4-O-isopropylidene-alpha-L-talopyranoside, using N-iodosuccinimide and triflic acid as the catalyst, to furnish 3-benzyloxycarbonylaminopropyl 6-deoxy-2-O[2,4-di-O-benzoyl-3-O-(3-O-benzyl-4-O-chloroacetyl-2-O-methyl-alpha-L-fucopyranosyl)-alpha-L-rhamnopyranosyl]-3,4-0-isopropylidene-alpha-L-talopyranoside (20). Selective removal of the chloroacetyl group from 20, followed by condensation with ethyl 2,3-di-O-benzoyl-4-O-methyl-1-thio-alpha-L-rhamnopyranoside in the presence of the same thiophilic promoter, yielded a fully protected tetrasaccharide derivative. Deprotection of the latter gave the target compound 3-aminopropyl 6-deoxy-2-O-{3-O-[2-O-methyl-(4-O-methyl-alpha-L-rhamnopyranosyl)-alpha-L-fucopyranosyl]-alpha-L-rhamnopyranosyl}alpha-L-talopyranoside (1).

  DOI：

  10.1016/0008-6215(93)80102-k

文献信息

• Iodonium ion-assisted synthesis of a haptenic tetrasaccharide fragment corresponding to the inner cell-wall glycopeptidolipid of Mycobacterium avium serotype 4
  作者：Helene M. Zuurmond、Gerrit H. Veeneman、Gijs A. van der Marel、Jacques H. van Boom

  DOI：10.1016/0008-6215(93)80102-k

  日期：1993.3

  Condensation of ethyl 2,4-di-O-benzoyl-1-thio-alpha-L-rhamnopyranoside with ethyl 3-O-benzyl-4-O-chloroacetyl-2-O-methyl-1-thio-beta-L-fucopyranoside in the presence of iodonium di-sym-collidine perchlorate afforded exclusively ethyl 2,4-di-O-benzoyl-3-O-(3-O-benzyl-4-O-chloroacetyl-2-O-methyl-alpha-L-fucopyranosyl)-1-thio-alpha-L-rhamnopyranoside. This disaccharide derivative was extended at C-1 with 3-benzyloxycarbonylaminopropyl 6-deoxy-3,4-O-isopropylidene-alpha-L-talopyranoside, using N-iodosuccinimide and triflic acid as the catalyst, to furnish 3-benzyloxycarbonylaminopropyl 6-deoxy-2-O[2,4-di-O-benzoyl-3-O-(3-O-benzyl-4-O-chloroacetyl-2-O-methyl-alpha-L-fucopyranosyl)-alpha-L-rhamnopyranosyl]-3,4-0-isopropylidene-alpha-L-talopyranoside (20). Selective removal of the chloroacetyl group from 20, followed by condensation with ethyl 2,3-di-O-benzoyl-4-O-methyl-1-thio-alpha-L-rhamnopyranoside in the presence of the same thiophilic promoter, yielded a fully protected tetrasaccharide derivative. Deprotection of the latter gave the target compound 3-aminopropyl 6-deoxy-2-O-3-O-[2-O-methyl-(4-O-methyl-alpha-L-rhamnopyranosyl)-alpha-L-fucopyranosyl]-alpha-L-rhamnopyranosyl}alpha-L-talopyranoside (1).