(2R,3R,4S,5S,6S)-5-Benzyloxy-6-methyl-4-((2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2,3-diol | 144174-57-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,5S,6S)-5-Benzyloxy-6-methyl-4-((2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2,3-diol
• CAS: 144174-57-2
• 化学式: C₂₂H₃₄O₉
• 分子量: 442.507
• InChiKey: VKIINSPYZRSRKN-YPLSSQAVSA-N

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (2R,3R,4S,5S,6S)-5-Benzyloxy-6-methyl-4-((2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2,3-diol 在 吡啶 作用下， 以90%的产率得到Acetic acid (2S,3R,4R,5S,6S)-2-acetoxy-5-benzyloxy-6-methyl-4-((2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Synthesis of methyl 3--[3--(2,3,4-tri--methyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl]-α-L-rhamnopyranoside : The outer trisaccharide unit of a unique glycopeptidolipid

  摘要：

  The combination of sugars present in Mycobacterium xenopi glycopeptidolipid (GPL X-1) has been characterised as O-(2,3,4-tri-O-methyl-alpha-L-rhamnopyranosyl)-(1-3)-O-(alpha-L-rhamnopyranosyl)-(1-3)-O-(alpha-L-rhamnopyranosyl)-(1-3)-6-deoxy-L-glucose. Two synthetic routes (A and B) towards the outer trisaccharide segment (2) have been designed. Route A involved the condensation of the aglycone (7) with 2,3,4-tri-O-acetyl-alpha-L-rhamnopyranosyl bromide (13) to afford which was sequentially deacetylated, methylated, deallylated and reacetylated to afford 12. Condensation of 12 with 16 in the presence of borontrifluoride etherate was unsuccessful. In route B, the disaccharide 21 was synthesised by the coupling reaction between 16 and 18 in the presence of borontrifluoride-etherate followed by deallylation. Alternatively, the disaccharide triacetate (22) was first prepared and routine modifications on it led to the formation of 21. Final condensation of 21 with the trichloroacetimidate (29) followed by sequential deacetylation, methylation and debenzylation afforded the trisaccharide (2).

  DOI：

  10.1016/s0040-4020(01)80018-1
• 作为产物：
  描述：

  allyl 2-O-allyl-4-O-benzyl-3-O-(2,3,4-tri-O-methyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside 在 Wilkinson's catalyst 三乙烯二胺 、 mercury dichloride 、 mercury(II) oxide 作用下， 生成 (2R,3R,4S,5S,6S)-5-Benzyloxy-6-methyl-4-((2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2,3-diol
  参考文献：
  名称：

  Synthesis of methyl 3--[3--(2,3,4-tri--methyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl]-α-L-rhamnopyranoside : The outer trisaccharide unit of a unique glycopeptidolipid

  摘要：

  The combination of sugars present in Mycobacterium xenopi glycopeptidolipid (GPL X-1) has been characterised as O-(2,3,4-tri-O-methyl-alpha-L-rhamnopyranosyl)-(1-3)-O-(alpha-L-rhamnopyranosyl)-(1-3)-O-(alpha-L-rhamnopyranosyl)-(1-3)-6-deoxy-L-glucose. Two synthetic routes (A and B) towards the outer trisaccharide segment (2) have been designed. Route A involved the condensation of the aglycone (7) with 2,3,4-tri-O-acetyl-alpha-L-rhamnopyranosyl bromide (13) to afford which was sequentially deacetylated, methylated, deallylated and reacetylated to afford 12. Condensation of 12 with 16 in the presence of borontrifluoride etherate was unsuccessful. In route B, the disaccharide 21 was synthesised by the coupling reaction between 16 and 18 in the presence of borontrifluoride-etherate followed by deallylation. Alternatively, the disaccharide triacetate (22) was first prepared and routine modifications on it led to the formation of 21. Final condensation of 21 with the trichloroacetimidate (29) followed by sequential deacetylation, methylation and debenzylation afforded the trisaccharide (2).

  DOI：

  10.1016/s0040-4020(01)80018-1