3-(tetra-O-benzoyl-α-D-glucopyranosyl)-1-propene | 98854-01-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(tetra-O-benzoyl-α-D-glucopyranosyl)-1-propene
• 英文别名: 3-(2',3',4',6'-tetra-O-benzoyl-α-D-glucopyranosyl)-1-propene；perbenzoylated α-C-allyl glucopyranoside；[(2R,3R,4R,5S,6R)-3,4,5-tribenzoyloxy-6-prop-2-enyloxan-2-yl]methyl benzoate
• CAS: 98854-01-4
• 化学式: C₃₇H₃₂O₉
• 分子量: 620.656
• InChiKey: FYLASGCMQNMGIZ-IZDBAANZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  46
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3-(tetra-O-benzoyl-α-D-glucopyranosyl)-1-propene 以100%的产率得到
  参考文献：
  名称：

  GRACIA, GARCIA MARTIN MARIA DE;HORTON, DEREK, CARBOHYDR. RES., 191,(1989) N, C. 223-229

  摘要：

  DOI：
• 作为产物：
  描述：

  Α-D-五苯甲酸酰吡喃葡萄糖 以43%的产率得到
  参考文献：
  名称：

  GRACIA, GARCIA MARTIN MARIA DE;HORTON, DEREK, CARBOHYDR. RES., 191,(1989) N, C. 223-229

  摘要：

  DOI：

文献信息

• Stereoselective synthesis of α- C-allyl-glycopyranosides
  作者：Athanassios Giannis、Konrad Sandhoff

  DOI：10.1016/s0040-4039(00)98529-0

  日期：——

  A simplified procedure for the synthesis of C-glycosides has been developed. Fully or partially acetylated glycopyranoses are reacted, in a single step, with allyltrimethylsilane in the presence of a Lewis acid. This method also offers the advantage that stereoselectivity can be induced by using appropriate solvents.

  已经开发了用于合成C-糖苷的简化程序。在路易斯酸的存在下，将完全或部分乙酰化的吡喃葡萄糖在一个步骤中与烯丙基三甲基硅烷反应。该方法还具有可以通过使用适当的溶剂来诱导立体选择性的优点。
• Preparative synthesis of C-(α-d-glucopyranosyl)-alkenes and -alkadienes: Diels-alder reaction
  作者：Maria de Gracia Garcia Martin、Derek Horton

  DOI：10.1016/0008-6215(89)85066-9

  日期：1989.8

  The reaction of 2,3,4,6-tetra-O-benzyl-1-O-(p-nitrobenzoyl)-alpha-D-glucopyranose with (E)-penta-2,4-dienyltrimethylsilane and boron trifluoride etherate in acetonitrile afforded stereoselectively (E)-5-(tetra-O-benzyl-alpha-D-glucopyranosyl)-1,3-pentadiene in good yield. The readily available penta-O-benzoyl-alpha-D-glucopyranose reacted with allyltrimethylsilane in the presence of boron trifluoride

  2,3,4,6-四-O-苄基-1-O-（对硝基苯甲酰基）-α-D-吡喃葡萄糖与（E）-戊-2,4-二烯基三甲基硅烷和三氟化硼醚化物在乙腈中的反应以良好的收率得到立体选择性地（E）-5-（四-O-苄基-α-D-吡喃葡萄糖基）-1,3-戊二烯。在乙腈中，在三氟化硼醚化物的存在下，易于获得的五-O-苯甲酰基-α-D-吡喃葡萄糖与烯丙基三甲基硅烷反应，生成3-（四-O-苯甲酰基-α-D-吡喃葡萄糖基）-1-丙烯及其β异构体的产率分别为60％和2.3％。将马来酸酐的Diels-Alder环加成成二烯1可以高收率得到加成物顺式，顺式3-（四-O-苄基-α-D-吡喃葡萄糖基甲基）环己基-4-烯-1,2-二羧酸酐。
• Studies on the Stereoselective Synthesis of <i>C</i>-Allyl Glycosides
  作者：Glenn J. McGarvey、Christopher A. LeClair、Bahar A. Schmidtmann

  DOI：10.1021/ol801710s

  日期：2008.11.6

  An investigation was carried out to explore the use of sulfoxide donors as common precursors to stereoisomeric C-glycoconjugates of glycoprotein and glycolipid tumor antigens. A study focusing on the effects of reaction conditions and substrate structure on the stereoselectivity of allylation was carried out. Although conditions were realized to selectively afford alpha-allylation products in good to excellent yields, the search for conditions favoring beta-selectivity proved less successful.
• Enzymatic Synthesis of a Selective Inhibitor for α-Glucosidases: α-Acarviosinyl-(1→9)-3-α-<scp>d</scp>-glucopyranosylpropen
  作者：Young-Su Lee、Myoung-Hee Lee、Hee-Seob Lee、Seung-Jae Lee、Young-Wan Kim、Ran Zhang、Stephen G. Withers、Kwan Soo Kim、Sung-Joon Lee、Kwan-Hwa Park

  DOI：10.1021/jf703655k

  日期：2008.7.1

  Here, we describe the enzymatic synthesis of novel inhibitors using acarviosine-glucose, as a donor and 3-alpha-D-glucopyranosylpropen (alpha GP) as an acceptor. Maltogenic amylase from Thermus sp. (ThMA) catalyzed the transglycosylation of the acarviosine moiety to alpha GP. The two major reaction products were isolated using chromatographies. Structural analyses revealed that acarviosine was transferred to either C-7 or C-9 of the alpha GP, which correspond to C-4 and C-6 of glucose. Both inhibited rat intestine (x-glucosidase competitively but displayed a mixed-type inhibition mode against human pancreatic alpha-amylase. The alpha-acarviosinyl-(1 -> 7)-3-alpha-D-glucopyranosylpropen showed weaker inhibition potency than acarbose against both alpha-glycosidases. In contrast, the alpha-acarviosinyl-(1 -> 9)-3-alpha-D-glucopyranosylpropen exhibited a 3.0-fold improved inhibition potency against rat intestine a-glucosidase with 0.3-fold inhibition potency against human pancreatic a-amylase relative to acarbose. In conclusion, alpha-acarviosinyl-(1 -> 9)-3-alpha-D-glucopyranosylpropen is a novel alpha-glucosidase-selective inhibitor with 10-fold enhanced selectivity toward alpha-glucosidase over alpha-amylase relative to acarbose, and it could be applied as a potent hypoglycemic agent.