ethyl 3-O-benzyl-4-O-chloroacetyl-2-O-methyl-1-thio-β-L-fucopyranoside | 143570-50-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 3-O-benzyl-4-O-chloroacetyl-2-O-methyl-1-thio-β-L-fucopyranoside
• 英文别名: [(2S,3R,4R,5S,6R)-6-ethylsulfanyl-5-methoxy-2-methyl-4-phenylmethoxyoxan-3-yl] 2-chloroacetate
• CAS: 143570-50-7
• 化学式: C₁₈H₂₅ClO₅S
• 分子量: 388.913
• InChiKey: FGOUIFGIXVLQBN-ARYPMIFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.24
• 重原子数：
  25.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl 3-O-benzyl-4-O-chloroacetyl-2-O-methyl-1-thio-β-L-fucopyranoside 在 三氟甲磺酸 N-碘代丁二酰亚胺 、 iodonium(di-γ-collidine) perchlorate 、 4 A molecular sieve 作用下， 以 乙醚 、 1,2-二氯乙烷 为溶剂， 反应 0.42h， 生成 3-benzyloxycarbonylaminopropyl 6-deoxy-2-O-<2,4-di-O-benzoyl-3-O-(3-O-benzyl-4-O-chloroacetyl-2-O-methyl-α-L-fucopyranosyl)-α-L-rhamnopyranosyl>-3,4-O-isopropylidene-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
• 作为产物：
  描述：

  S-ethyl 3,4-O-isopropylidene-2-O-methyl-1-thio-β-D-fucopyranoside 在 二正丁基氧化锡 、 碳酸氢钠 、 溶剂黄146 、 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 39.0h， 生成 ethyl 3-O-benzyl-4-O-chloroacetyl-2-O-methyl-1-thio-β-L-fucopyranoside
  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 glycosylation of alkyl (aryl) 1-thio-glycosides: regulation of stereoselectivity and reactivity
  作者：Helene M. Zuurmond、Susanne C. van der Laan、Gijs A. van der Marel、Jacques H. van Boom

  DOI：10.1016/0008-6215(91)84036-e

  日期：1991.8