6-O-acetyl-2,3,4-tri-O-benzoyl-D-glucopyranosyl trichloroacetimidate | 485807-57-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 6-O-acetyl-2,3,4-tri-O-benzoyl-D-glucopyranosyl trichloroacetimidate
• 英文别名: Bz(-2)[Bz(-3)][Bz(-4)]Glc6Ac-O-C(NH)CCl3；[(2R,3R,4S,5R)-2-(acetyloxymethyl)-4,5-dibenzoyloxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl] benzoate
• CAS: 485807-57-6
• 化学式: C₃₁H₂₆Cl₃NO₁₀
• 分子量: 678.907
• InChiKey: LMPRSGVCSGTWDZ-TVPGJJFGSA-N

物化性质

• 沸点：
  701.3±70.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  45
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  148
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  6-O-acetyl-2,3,4-tri-O-benzoyl-D-glucopyranosyl trichloroacetimidate 在 盐酸 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 49.0h， 生成 toralactone 9-O-yl 6-O-acetyl-2,3,4-tri-O-benzoyl-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-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：

  2,3,4-tri-O-benzoyl-6-O-acetyl-α-D-glucopyranosyl bromide 在 potassium carbonate 、 silver carbonate 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 0.67h， 生成 6-O-acetyl-2,3,4-tri-O-benzoyl-D-glucopyranosyl trichloroacetimidate
  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

文献信息

• Synthesis of 3-aminopropyl β-(1 → 6)-d-glucotetraoside and its biotinylated derivative
  作者：Dmitry V. Yashunsky、Alexander A. Karelin、Yury E. Tsvetkov、Nikolay E. Nifantiev

  DOI：10.1016/j.carres.2017.11.001

  日期：2018.1

  3-Aminopropyl β-(1 → 6)-d-glucotetraoside has been synthesized from 3-benzyloxycarbonylaminopropanol and 6-O-acetyl-2,3,4-tri-O-benzoyl-d-glucopyranosyl trichloroacetimidate by successive attachment of one monosaccharide unit in total yield of 22%. Free aminopropyl glycoside was converted into a biotin derivative that can be used for controlled immobilization of the oligosaccharide on streptavidin-coated

  由3-苄氧基羰基氨基丙醇和6-O-乙酰基-2,3,4-三-O-苯甲酰基-d-吡喃葡萄糖基三氯乙亚氨酸酯合成3-氨基丙基β-（1→6）-d-葡萄糖四糖苷总产量的22％。游离的氨基丙基糖苷被转化为生物素衍生物，可用于寡糖在链霉亲和素包被的ELISA板上的可控固定和追踪碳水化合物结合分子。
• Synthesis of 3-aminopropyl glycosides of branched β-(1→3)-glucooligosaccharides
  作者：D. V. Yashunsky、Yu. E. Tsvetkov、N. E. Nifantiev

  DOI：10.1007/s11172-015-1249-z

  日期：2015.12

  The synthesis of branched β-(1→3)-glucooligosaccharides bearing a β-d-glucose residue at position 6 of one of the monosaccharides of the linear chain at a different distances from the reducing end was described.

  描述了在距还原端不同距离的直链单糖之一的第 6 位带有 β-d-葡萄糖残基的支链 β-(1→3)-葡萄糖寡糖的合成。
• Synthesis and Biological Evaluation of Cyanogenic Glycosides
  作者：Dmitry V. Yashunsky、Ekaterina V. Kulakovskaya、Tatiana V. Kulakovskaya、Olga S. Zhukova、Mikhail V. Kiselevskiy、Nikolay E. Nifantiev

  DOI：10.1080/07328303.2015.1105249

  日期：2015.10.13

  An efficient procedure for the synthesis of cyanogenic glycosides with different carbohydrate units was developed. Amygdalin (3), prunasin (1), sambunigrin (2), and neoamygdalin (21) were prepared according to the elaborated method, and biological tests, including antifungal, antibacterial, and cytotoxic activities, were performed.