4-<2-(benzyloxycarbonylamino)ethyl>phenyl 2,4-di-O-methyl-3-O-<4-O-benzyl-2-O-methyl-3-O-(4-O-acetyl-2-O-methyl-α-L-fucopyranosyl)α-L-rhamnopyranosyl>-α-L-rhamnopyranoside | 146399-72-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-<2-(benzyloxycarbonylamino)ethyl>phenyl 2,4-di-O-methyl-3-O-<4-O-benzyl-2-O-methyl-3-O-(4-O-acetyl-2-O-methyl-α-L-fucopyranosyl)α-L-rhamnopyranosyl>-α-L-rhamnopyranoside
• 英文别名: Zyhyzenxihjkqi-ssrodrshsa-；[(2S,3S,4R,5S,6S)-6-[(2S,3R,4R,5S,6S)-2-[(2S,3S,4R,5R,6S)-3,5-dimethoxy-2-methyl-6-[4-[2-(phenylmethoxycarbonylamino)ethyl]phenoxy]oxan-4-yl]oxy-3-methoxy-6-methyl-5-phenylmethoxyoxan-4-yl]oxy-4-hydroxy-5-methoxy-2-methyloxan-3-yl] acetate
• CAS: 146399-72-6
• 化学式: C₄₇H₆₃NO₁₆
• 分子量: 898.014
• InChiKey: ZYHYZENXIHJKQI-SSRODRSHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  64
• 可旋转键数：
  21
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  186
• 氢给体数：
  2
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  4-<2-(benzyloxycarbonylamino)ethyl>phenyl 2,4-di-O-methyl-3-O-<4-O-benzyl-2-O-methyl-3-O-(4-O-acetyl-2-O-methyl-α-L-fucopyranosyl)α-L-rhamnopyranosyl>-α-L-rhamnopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 水 、 溶剂黄146 、 异丙醇 为溶剂， 反应 18.0h， 以60 mg的产率得到4-(aminoethyl)phenyl 2,4-di-O-methyl-3-O-<2-O-methyl-3-O-(4-O-acetyl-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：

  4-<2-(benzyloxycarbonylamino)ethyl>phenyl 2,4-di-O-methyl-α-L-rhamnopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 MS 4 Angstroem 、 potassium tert-butylate 作用下， 以 甲醇 、 乙醚 、 溶剂黄146 、 1,2-二氯乙烷 为溶剂， 反应 26.25h， 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-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

文献信息

• Iodonium ion-assisted synthesis of tetrameric fragments corresponding to the cell wall phenolic glycolipids of Mycobacterium kansasii serovars II and IV
  作者：Korien Zegelaar-Jaarsveld、Howard I. Duynstee、Gijs A. van der Marel、Jacques H. van Boom

  DOI：10.1016/0040-4020(96)00034-8

  日期：1996.3

  The spacer-containing tetramers 3 and 4, derivatives of the phenolic glycolipids of Mycobacterium kansasii serovars II and IV were prepared by iodonium ion-mediated mannosylation of trimeric acceptor 4-[2-(benzyloxycarbonylamino)ethyl]phenyl (2) with ethyl 1-thio-d-mannopyranoside donors 7, 13, and 24. In addition, the glycosylating properties of donors 7, 13, 24, 29–31, each containing a different

  含间隔基的四聚体3和4，堪萨斯分枝杆菌血清型II和IV的酚糖脂衍生物是通过碘离子介导的三聚体受体4- [2-（苄氧基羰基氨基）乙基]苯基（2）与1-乙基的甘露糖基化反应制得的。硫代d-D-吡喃甘露糖苷供体7，13，和24。此外，供体的糖基化特性7，13，24，29-31，每个包含一个不同的保护基团在2位，通过用模型受体执行缩合检查18（L）和其对映体18（d）。
• Iodonium ion-assisted synthesis of a tetrameric fragment corresponding to the cell wall phenolic glycolipids of Mycobacterium kansasii serovar I
  作者：Korien Zegelaar-Jaarsveld、Sander A.W. Smits、Nicole C.R. van Straten、Gijs A. van der Marel、Jacques H. van Boom

  DOI：10.1016/0040-4020(96)00035-x

  日期：1996.3

  Two procedures are described towards the assembly of the tyramine spacer-containing tetramer 5, a derivative of the phenolic glycolipid of Mycobacterium kansasii serovar I. First, iodonium ion-mediated glycosylation of trimeric acceptor 2a with D-rhamnopyranoside donor 10 gave fully protected tetramer 17. Selective removal of the chloroacetyl group of 17, subsequent deoxygenation and removal of the protective groups, led to target 5. The potential occurrence of double stereodifferentiation (DSD) was examined by condensation of L-fucopyranoside model acceptor 14 with both the enantiomeric rhamnopyranoside donors 10 and 13. The second procedure involves elongation of trimeric acceptor 2b with 6-deoxy-D-glucopyranoside 28. Desulfurisation of the resulting tetrameric fragment 36 followed by hydrogenation of 37 gave 38, the phenylacetyl (PhAc) of which was enzymatically removed to yield target tetramer 5.