allyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-α-D-glucopyranoside | 590367-98-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-α-D-glucopyranoside
• CAS: 590367-98-9
• 化学式: C₇₇H₆₈O₂₄
• 分子量: 1377.37
• InChiKey: RAOLJXPUAUVFHQ-PYZLAZBSSA-N

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 allyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-α-D-glucopyranoside 在 吡啶 作用下， 以97%的产率得到allyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-glucopyranosyl-(1->3)-4,6-di-O-acetyl-2-O-benzoyl-α-D-glucopyranoside
  参考文献：
  名称：

  Total Synthesis of the Antiallergic Naphtho-α-pyrone Tetraglucoside, Cassiaside C₂, Isolated from Cassia Seeds

  摘要：

  Toralactone 9-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside (1, cassiaside C-2) isolated from Cassia obtusifolia L. and showing strong antiallergic activity, was concisely synthesized employing glycosyl trifluoroacetimidates as glycosylation agents. The unique naphtho-alpha-pyrone structure of toralactone (5) was constructed by condensation of orsellinate 8 with pyrone 9 in the presence of LDA as developed by Staunton and co-workers. The naphthol of toralactone showed minimal reactivity as an acceptor and was screened with various glycosyl donors. It is finally concluded that sacrifice of an excess amount of the trifluoroacetimidate or trichloroacetimidate donors (6f/6g, 6.0 equiv) in the presence of a catalytic amount of TMSOTf (0.05 and 0.3 equiv, respectively) afforded excellent yields of the coupling product, which was otherwise only a minor product under a variety of conditions examined.

  DOI：

  10.1021/jo034223u
• 作为产物：
  描述：

  allyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside 在 溶剂黄146 作用下， 反应 10.0h， 以78%的产率得到allyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-α-D-glucopyranoside
  参考文献：
  名称：

  Total Synthesis of the Antiallergic Naphtho-α-pyrone Tetraglucoside, Cassiaside C₂, Isolated from Cassia Seeds

  摘要：

  Toralactone 9-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside (1, cassiaside C-2) isolated from Cassia obtusifolia L. and showing strong antiallergic activity, was concisely synthesized employing glycosyl trifluoroacetimidates as glycosylation agents. The unique naphtho-alpha-pyrone structure of toralactone (5) was constructed by condensation of orsellinate 8 with pyrone 9 in the presence of LDA as developed by Staunton and co-workers. The naphthol of toralactone showed minimal reactivity as an acceptor and was screened with various glycosyl donors. It is finally concluded that sacrifice of an excess amount of the trifluoroacetimidate or trichloroacetimidate donors (6f/6g, 6.0 equiv) in the presence of a catalytic amount of TMSOTf (0.05 and 0.3 equiv, respectively) afforded excellent yields of the coupling product, which was otherwise only a minor product under a variety of conditions examined.

  DOI：

  10.1021/jo034223u