phenyl 4-O-benzyl-2-O-methyl-1-thio-α-L-rhamnopyranoside | 146399-75-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 4-O-benzyl-2-O-methyl-1-thio-α-L-rhamnopyranoside
• 英文别名: (2S,3R,4R,5R,6S)-5-methoxy-2-methyl-3-phenylmethoxy-6-phenylsulfanyloxan-4-ol
• CAS: 146399-75-9
• 化学式: C₂₀H₂₄O₄S
• 分子量: 360.474
• InChiKey: JMOKRHVNDSGVHL-AXBXVSCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  73.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  phenyl 4-O-benzyl-2-O-methyl-1-thio-α-L-rhamnopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 iodonium(di-γ-collidine) perchlorate 、 4 A molecular sieve 、 MS 4 Angstroem 作用下， 以 乙醚 、 1,2-二氯乙烷 为溶剂， 反应 3.25h， 生成 4-<2-(benzyloxycarbonylamino)ethyl>phenyl 2,4-di-O-methyl-3-O-<4-O-benzyl-2-O-methyl-3-O-(4-O-acetyl-3-O-(p-methoxybenzyl)-2-O-methyl-α-L-fucopyranosyl)-α-L-rhamnopyranosyl>-α-L-rhamnopyranoside
  参考文献：
  名称：

  Iodonium ion assisted synthesis of a common inner core trisaccharide fragment corresponding to the cell-wall phenolic glycolipid of Mycobacterium kansasii

  摘要：

  The spacer containing trimer 4-(aminoethyl)phenyl 2,4-di-O-Me-3-O-[2-O-methyl-3-O-(4-O-acetyl-2-O-methyl-alpha-L-fucopyranosyl)-alpha-L-rhamnopyranosyl]-alpha-L-rhamnopyranoside (2) was prepared by stepwise extension of 4-[2-(benzyloxycarbonyl-amino)ethyl]phenyl 2,4-di-O-methyl-alpha-L-rhamnopyranoside (19) with property protected ethyl thioglycosides of L-rhamnose 8 and L-fucose 12 or 16 using iodonium ions as promotors. The resulting trimers 22 or 23 were deblocked in two steps to give homogeneous 2. Alternatively, fully protected trimer 22 was assembled by iodonium ion assisted condensation of the phenyl 1-thio-alpha-L-rhamnopyranoside 29 with 12 followed by extension of dimer 31 with 19.

  DOI：

  10.1016/s0040-4020(01)89043-8
• 作为产物：
  描述：

  phenyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside 在 sodium hydroxide 、 四丁基碘化铵 、 potassium hydride 作用下， 以 二氯甲烷 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 117.25h， 生成 phenyl 4-O-benzyl-2-O-methyl-1-thio-α-L-rhamnopyranoside
  参考文献：
  名称：

  Iodonium ion assisted synthesis of a common inner core trisaccharide fragment corresponding to the cell-wall phenolic glycolipid of Mycobacterium kansasii

  摘要：

  The spacer containing trimer 4-(aminoethyl)phenyl 2,4-di-O-Me-3-O-[2-O-methyl-3-O-(4-O-acetyl-2-O-methyl-alpha-L-fucopyranosyl)-alpha-L-rhamnopyranosyl]-alpha-L-rhamnopyranoside (2) was prepared by stepwise extension of 4-[2-(benzyloxycarbonyl-amino)ethyl]phenyl 2,4-di-O-methyl-alpha-L-rhamnopyranoside (19) with property protected ethyl thioglycosides of L-rhamnose 8 and L-fucose 12 or 16 using iodonium ions as promotors. The resulting trimers 22 or 23 were deblocked in two steps to give homogeneous 2. Alternatively, fully protected trimer 22 was assembled by iodonium ion assisted condensation of the phenyl 1-thio-alpha-L-rhamnopyranoside 29 with 12 followed by extension of dimer 31 with 19.

  DOI：

  10.1016/s0040-4020(01)89043-8

文献信息

• Iodonium ion assisted synthesis of a common inner core trisaccharide fragment corresponding to the cell-wall phenolic glycolipid of Mycobacterium kansasii
  作者：Korien Zegelaar-Jaarsveld、Gijs A. van der Marel、Jacues H. van Boom

  DOI：10.1016/s0040-4020(01)89043-8

  日期：——

  The spacer containing trimer 4-(aminoethyl)phenyl 2,4-di-O-Me-3-O-[2-O-methyl-3-O-(4-O-acetyl-2-O-methyl-alpha-L-fucopyranosyl)-alpha-L-rhamnopyranosyl]-alpha-L-rhamnopyranoside (2) was prepared by stepwise extension of 4-[2-(benzyloxycarbonyl-amino)ethyl]phenyl 2,4-di-O-methyl-alpha-L-rhamnopyranoside (19) with property protected ethyl thioglycosides of L-rhamnose 8 and L-fucose 12 or 16 using iodonium ions as promotors. The resulting trimers 22 or 23 were deblocked in two steps to give homogeneous 2. Alternatively, fully protected trimer 22 was assembled by iodonium ion assisted condensation of the phenyl 1-thio-alpha-L-rhamnopyranoside 29 with 12 followed by extension of dimer 31 with 19.