(E)-4-Oxobut-2-enyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside | 131474-50-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子
• 英文名称: (E)-4-Oxobut-2-enyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[(E)-4-oxobut-2-enoxy]oxan-2-yl]methyl acetate
• CAS: 131474-50-5
• 化学式: C₁₈H₂₄O₁₁
• 分子量: 416.382
• InChiKey: KALRHFLYJHAGHS-JEFIQMRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.16
• 重原子数：
  29.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  140.73
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (E)-4-Oxobut-2-enyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside 在 吡啶 、 sodium azide 、 sodium methylate 、 sodium cyanoborohydride 作用下， 以 乙醇 、 水 、 溶剂黄146 、 丙酮 为溶剂， 反应 11.67h， 生成 Methyl 4-S-(3-azido-4-α-maltosyloxybutyl)-6-deoxy-4-thio-α-D-xylo-hex-5-enopyranoside
  参考文献：
  名称：

  Photolabile, spacer-modified oligosaccharides for probing malto-oligosaccharide binding sites in proteins

  摘要：

  O-Deacylation and S-deacylation of the diastereomers of 2-azido-4-S-benzoyl-4-mercaptobutyl 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranoside (9) with methanolic sodium methoxide and coupling of the resulting thiol to methyl 3,4-anhydro-6-deoxy-beta-L-arabino-hex-5-enopyranoside (2) gave the corresponding diastereomers of the spacer-modified disaccharide methyl 4-S-(3-azido-4-alpha-D-glucopyranosyloxybutyl)-6-deoxy-4-thio-alph a-D-xylo-hex-5-enopyranoside (10). Glucosylation of the diastereomers of 10 with alpha-cyclo-dextrin-CGTase and treatment of the products with beta-amylase gave the diastereomers of the spacer-modified oligosaccharides methyl 4-S-(3-azido-4-alpha-maltosyloxybutyl)-6-deoxy-4-thio-alpha-D-xylo -hex-5-enopyranosides (11) and 4-S-(3-azido-4-alpha-maltotriosyloxybutyl)-6-deoxy-4-thio-alpha-D- hex-5-enopyranosides (12). The diastereomers of 10 each had a good affinity for pancreatic alpha-amylase and the maltose-binding protein from E. coli. The affinities of the diastereomers of 11 and 12 were higher by at least one order of magnitude.

  DOI：

  10.1016/0008-6215(90)80131-l
• 作为产物：
  描述：

  allyl-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside 在 氧气 、 臭氧 作用下， 以 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 1.25h， 生成 (E)-4-Oxobut-2-enyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside
  参考文献：
  名称：

  Photolabile, spacer-modified oligosaccharides for probing malto-oligosaccharide binding sites in proteins

  摘要：

  O-Deacylation and S-deacylation of the diastereomers of 2-azido-4-S-benzoyl-4-mercaptobutyl 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranoside (9) with methanolic sodium methoxide and coupling of the resulting thiol to methyl 3,4-anhydro-6-deoxy-beta-L-arabino-hex-5-enopyranoside (2) gave the corresponding diastereomers of the spacer-modified disaccharide methyl 4-S-(3-azido-4-alpha-D-glucopyranosyloxybutyl)-6-deoxy-4-thio-alph a-D-xylo-hex-5-enopyranoside (10). Glucosylation of the diastereomers of 10 with alpha-cyclo-dextrin-CGTase and treatment of the products with beta-amylase gave the diastereomers of the spacer-modified oligosaccharides methyl 4-S-(3-azido-4-alpha-maltosyloxybutyl)-6-deoxy-4-thio-alpha-D-xylo -hex-5-enopyranosides (11) and 4-S-(3-azido-4-alpha-maltotriosyloxybutyl)-6-deoxy-4-thio-alpha-D- hex-5-enopyranosides (12). The diastereomers of 10 each had a good affinity for pancreatic alpha-amylase and the maltose-binding protein from E. coli. The affinities of the diastereomers of 11 and 12 were higher by at least one order of magnitude.

  DOI：

  10.1016/0008-6215(90)80131-l

文献信息

• LEHMANN, JOCHEN;ZISER, LOTHAR, CARBOHYDR. RES., 205,(1990) C. 93-103
  作者：LEHMANN, JOCHEN、ZISER, LOTHAR

  DOI：——

  日期：——