ethyl 3-O-(p-methoxybenzyl)-2-O-methyl-1-thio-β-L-fucopyranoside | 146399-62-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 3-O-(p-methoxybenzyl)-2-O-methyl-1-thio-β-L-fucopyranoside
• 英文别名: (2S,3R,4R,5S,6R)-6-ethylsulfanyl-5-methoxy-4-[(4-methoxyphenyl)methoxy]-2-methyloxan-3-ol
• CAS: 146399-62-4
• 化学式: C₁₇H₂₆O₅S
• 分子量: 342.456
• InChiKey: JBZQVZMAWDQWBE-PAZMTAOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  82.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 3-O-(p-methoxybenzyl)-2-O-methyl-1-thio-β-L-fucopyranoside 在 4-二甲氨基吡啶 、 4 Angstroem MS 、 四丁基溴化铵 、 一水合肼 、 copper(ll) bromide 作用下， 以 吡啶 、 丙醇 、 二氯甲烷 为溶剂， 反应 106.0h， 生成 [(2S,3R,4R,5S,6R)-6-[[(2R,3S,4R,5R,6R)-5-acetamido-3-[(2S,3R,4R,5S,6R)-3-azido-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-4,6-bis(phenylmethoxy)oxan-2-yl]methoxy]-5-methoxy-4-[(4-methoxyphenyl)methoxy]-2-methyloxan-3-yl] acetate
  参考文献：
  名称：

  Synthesis of lipooligosaccharides related to nodulation factors ofRhizobium sp. NGR234

  摘要：

  Trisaccharide analogs of natural nodulation factors from Rhizobium sp. NGR234, namely, 2-acetamido-2-deoxy-4-O-(2-deoxy-2-hexadecanamido-beta-D-glucopyranosyl)-6-O- (2-O-methyl-alpha-L-fucopyranosyl)-D-glucopyranose and its derivatives containing a 4-O-acetyl or a 3-O-sulfo group at the L-fucose residue, were synthesized. The oligosaccharides synthesized were shown to possess biological activity.

  DOI：

  10.1007/bf02495661
• 作为产物：
  描述：

  ethyl 1-thio-β-L-fucopyranoside 在 氢氧化钾 、 四乙基溴化铵 、 二正丁基氧化锡 、 对甲苯磺酸 、 三氟乙酸 作用下， 以 氯仿 、 二甲基亚砜 为溶剂， 反应 24.75h， 生成 ethyl 3-O-(p-methoxybenzyl)-2-O-methyl-1-thio-β-L-fucopyranoside
  参考文献：
  名称：

  Synthesis of lipooligosaccharides related to nodulation factors ofRhizobium sp. NGR234

  摘要：

  Trisaccharide analogs of natural nodulation factors from Rhizobium sp. NGR234, namely, 2-acetamido-2-deoxy-4-O-(2-deoxy-2-hexadecanamido-beta-D-glucopyranosyl)-6-O- (2-O-methyl-alpha-L-fucopyranosyl)-D-glucopyranose and its derivatives containing a 4-O-acetyl or a 3-O-sulfo group at the L-fucose residue, were synthesized. The oligosaccharides synthesized were shown to possess biological activity.

  DOI：

  10.1007/bf02495661

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.
• Synthesis of lipooligosaccharides related to nodulation factors ofRhizobium sp. NGR234
  作者：A. I. Zinin、V. I. Torgov、V. N. Shibaev、A. S. Shashkov、W. J. Broughton

  DOI：10.1007/bf02495661

  日期：1998.3

  Trisaccharide analogs of natural nodulation factors from Rhizobium sp. NGR234, namely, 2-acetamido-2-deoxy-4-O-(2-deoxy-2-hexadecanamido-beta-D-glucopyranosyl)-6-O- (2-O-methyl-alpha-L-fucopyranosyl)-D-glucopyranose and its derivatives containing a 4-O-acetyl or a 3-O-sulfo group at the L-fucose residue, were synthesized. The oligosaccharides synthesized were shown to possess biological activity.