Phenyl-O-(α-D-glucopyranosyl)-(1->4)-(α-D-glucopyranosyl)-(1->4)-D-glucopyranosid | 39026-60-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Phenyl-O-(α-D-glucopyranosyl)-(1->4)-(α-D-glucopyranosyl)-(1->4)-D-glucopyranosid
• 英文别名: Glc(a1-4)Glc(a1-4)Glc(a)-O-Ph；(2R,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-6-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-phenoxyoxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 39026-60-3
• 化学式: C₂₄H₃₆O₁₆
• 分子量: 580.54
• InChiKey: QWNCOASHVFFDRG-XFNLHOCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.2
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  258
• 氢给体数：
  10
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  Phenyl-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-D-glucopyranosid 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 Phenyl-O-(α-D-glucopyranosyl)-(1->4)-(α-D-glucopyranosyl)-(1->4)-D-glucopyranosid 、 Phenyl-O-(α-D-glucopyranosyl)-(1->4)-(α-D-glucopyranosyl)-(1->4)-D-glucopyranosid
  参考文献：
  名称：

  α-葡萄糖苷酶抑制剂，2.合成的麦芽三糖的合成

  摘要：

  已经开发出两种合成路线用于生产4”-氨基-4”，6”-二脱氧麦芽三糖衍生物5，即阿卡波糖的O-保护的末端三糖单元。4'-未保护的麦芽糖衍生物3与4-azido-4,6-dideoxyglucose 1的三氯乙二酸酯2进行糖苷化反应，产生α-和β-连接的三糖4和9，它们被转化为O-保护的氨基糖5和10。另外，苯基麦芽三糖苷15成为4″，6″-未保护的衍生物19。通过选择性脱氧和叠氮化物的引入从中获得4和5。

  DOI：

  10.1002/jlac.198319831106

文献信息

• Optimized synthesis of specific sizes of maltodextrin glycosides by the coupling reactions of Bacillus macerans cyclomaltodextrin glucanyltransferase
  作者：Seung-Heon Yoon、John F. Robyt

  DOI：10.1016/j.carres.2005.11.014

  日期：2006.2

  Bacillus macerans cyclomaltodextrin glucanyltransferase (CGTase, EC 2.4.1.19), in reaction with cyclomaltohexaose and methyl alpha-D-glucopyranoside, methyl beta-D-glucopyranoside, phenyl alpha-D-glucopyranoside, and phenyl beta-D-glucopyranoside gave four kinds of maltodextrin glycosides. The reactions were optimized by using different ratios of the individual D-glucopyranosides to cyclomaltohexaose, from 0.5 to 5.0, to obtain the maximum molar percent yields of products, which were from 68.3% to 78.6%, depending on the particular D-glucopyranoside, and also to obtain different maltodextrin chain lengths. The lower ratios of 0.5-1.0 gave a wide range of sizes from d.p. 2-17 and higher. As the molar ratio was increased from 1.0 to 3.0, the larger sizes, d.p. 9-17, decreased, and the small and intermediate sizes, d.p. 2-8, increased; as the molar ratios were increased further from 3.0 to 5.0, the large sizes completely disappeared, the intermediate sizes, d.p. 4-8, decreased, and the small sizes, d.p. 2 and 3 became predominant. A comparison is made with the synthesis of maltodextrins by the reaction of CGTase with different molar ratios Of D-glucose to cyclomaltohexaose. (c) 2005 Elsevier Ltd. All rights reserved.
• α-Glucosidasen-Inhibitoren, 2. Synthese von modifizierten Maltotriosen
  作者：Klaus Laesecke、Richard R. Schmidt

  DOI：10.1002/jlac.198319831106

  日期：1983.11.15

  6″-didesoxymaltotriosederivats 5, der O-geschützten terminalen Trisaccharideinheit der Acarbose, wurden zwei Synthesewege entwickelt. Glycosidierung des 4′-ungeschützten Maltosederivats 3 mit dem Trichloracetimidat 2 der 4-Azido-4,6-didesoxyglucose 1 lieferte die α- bzw. β-verknüpften Trisaccharide 4 und 9, die in die O-geschützten Aminozucker 5 und 10 übergeführt werden. Außerdem wurde aus dem Phenylmaltotriosid

  已经开发出两种合成路线用于生产4”-氨基-4”，6”-二脱氧麦芽三糖衍生物5，即阿卡波糖的O-保护的末端三糖单元。4'-未保护的麦芽糖衍生物3与4-azido-4,6-dideoxyglucose 1的三氯乙二酸酯2进行糖苷化反应，产生α-和β-连接的三糖4和9，它们被转化为O-保护的氨基糖5和10。另外，苯基麦芽三糖苷15成为4″，6″-未保护的衍生物19。通过选择性脱氧和叠氮化物的引入从中获得4和5。