1,2,3,4-tetra-O-levulinoyl-α-D-xylopyranose | 343254-30-8

• 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: 1,2,3,4-tetra-O-levulinoyl-α-D-xylopyranose
• 英文别名: [(3R,4S,5R,6R)-4,5,6-tris(4-oxopentanoyloxy)oxan-3-yl] 4-oxopentanoate
• CAS: 343254-30-8
• 化学式: C₂₅H₃₄O₁₃
• 分子量: 542.537
• InChiKey: KIIWREMPPGWCOI-XUVDGOIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  38
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  183
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetra-O-levulinoyl-α-D-xylopyranose 在 4 Angstroem MS 、 silver trifluoromethanesulfonate 、 四氯化钛 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 4.0h， 生成 N-benzyloxycarbonyl-O-(2,3,4-tri-O-levulinoyl-β-D-xylopyranosyl)-L-serine benzyl ester
  参考文献：
  名称：

  Synthesis of Phosphorylated and Sulfated Glycosyl Serines in the Linkage Region of the Glycosaminoglycans

  摘要：

  We synthesized novel acidic glycans having acidic groups located in the linkage region of the glycosaminoglcans (GAGs). The targeted compounds, beta -D-Xyl(2P)-Ser (1), beta -D-Gal(+/- 6S)-(1 -->4)-beta- D-Xyl(2P)-Ser (3 and 2), beta -D-Gal(+/- 6S)-(1 -->3)-beta -D-Gal-(1 -->4)-beta -D-Xyl(2P)-Ser (5 and 4), and beta -D-Gal- (1 -->3)-beta -D-Gal(6S)-(1 -->4)-beta -D-Xyl(2P)-Ser (6) contain phosphate and/or sulfate at the specified positions. Some of them (3,5, and 6) are the first synthesized examples of natural-type glycoconjugates that simultaneously possess phosphate and sulfate as well as carboxylic acid.

  DOI：

  10.1021/jo001540h
• 作为产物：
  描述：

  D-吡喃木糖 、 乙酰丙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 1,2-二氯乙烷 为溶剂， 以86%的产率得到1,2,3,4-tetra-O-levulinoyl-α-D-xylopyranose
  参考文献：
  名称：

  Synthesis of Phosphorylated and Sulfated Glycosyl Serines in the Linkage Region of the Glycosaminoglycans

  摘要：

  We synthesized novel acidic glycans having acidic groups located in the linkage region of the glycosaminoglcans (GAGs). The targeted compounds, beta -D-Xyl(2P)-Ser (1), beta -D-Gal(+/- 6S)-(1 -->4)-beta- D-Xyl(2P)-Ser (3 and 2), beta -D-Gal(+/- 6S)-(1 -->3)-beta -D-Gal-(1 -->4)-beta -D-Xyl(2P)-Ser (5 and 4), and beta -D-Gal- (1 -->3)-beta -D-Gal(6S)-(1 -->4)-beta -D-Xyl(2P)-Ser (6) contain phosphate and/or sulfate at the specified positions. Some of them (3,5, and 6) are the first synthesized examples of natural-type glycoconjugates that simultaneously possess phosphate and sulfate as well as carboxylic acid.

  DOI：

  10.1021/jo001540h

文献信息

• Synthesis of Phosphorylated and Sulfated Glycosyl Serines in the Linkage Region of the Glycosaminoglycans
  作者：Jun-ichi Tamura、Junko Nishihara

  DOI：10.1021/jo001540h

  日期：2001.5.1

  We synthesized novel acidic glycans having acidic groups located in the linkage region of the glycosaminoglcans (GAGs). The targeted compounds, beta -D-Xyl(2P)-Ser (1), beta -D-Gal(+/- 6S)-(1 -->4)-beta- D-Xyl(2P)-Ser (3 and 2), beta -D-Gal(+/- 6S)-(1 -->3)-beta -D-Gal-(1 -->4)-beta -D-Xyl(2P)-Ser (5 and 4), and beta -D-Gal- (1 -->3)-beta -D-Gal(6S)-(1 -->4)-beta -D-Xyl(2P)-Ser (6) contain phosphate and/or sulfate at the specified positions. Some of them (3,5, and 6) are the first synthesized examples of natural-type glycoconjugates that simultaneously possess phosphate and sulfate as well as carboxylic acid.