3-benzyloxycarbonylaminopropyl 2,3,4-tri-O-benzoyl-α-L-rhamnopyranoside | 148404-64-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-benzyloxycarbonylaminopropyl 2,3,4-tri-O-benzoyl-α-L-rhamnopyranoside
• CAS: 148404-64-2
• 化学式: C₃₈H₃₇NO₁₀
• 分子量: 667.712
• InChiKey: UNIAYLDLWZUHMF-IBEVXSELSA-N

物化性质

• 沸点：
  798.0±60.0 °C(predicted)
• 密度：
  1.31±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.74
• 重原子数：
  49.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  135.69
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  3-benzyloxycarbonylaminopropyl 2,3,4-tri-O-benzoyl-α-L-rhamnopyranoside 在 potassium tert-butylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 [3-((2R,3R,4R,5R,6S)-3,4,5-Trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-propyl]-carbamic acid benzyl ester
  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
• 作为产物：
  描述：

  3-(苄氧羰基氨基)-1-丙醇 、 ethyl 2,3,4-tri-O-benzoyl-1-thio-α-L-rhamnopyranoside 在 三氟甲磺酸 N-碘代丁二酰亚胺 、 4 A molecular sieve 作用下， 以 乙醚 、 1,2-二氯乙烷 为溶剂， 反应 0.25h， 以81%的产率得到3-benzyloxycarbonylaminopropyl 2,3,4-tri-O-benzoyl-α-L-rhamnopyranoside
  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