N-benzyloxycarbonyl-O-(4-O-chloroacetyl-β-D-xylopyranosyl)-L-serine benzyl ester | 244022-39-7

• 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: N-benzyloxycarbonyl-O-(4-O-chloroacetyl-β-D-xylopyranosyl)-L-serine benzyl ester
• 英文别名: benzyl (2S)-3-[(2R,3R,4R,5R)-5-(2-chloroacetyl)oxy-3,4-dihydroxyoxan-2-yl]oxy-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 244022-39-7
• 化学式: C₂₅H₂₈ClNO₁₀
• 分子量: 537.951
• InChiKey: RZYHGVWRJKRINS-AGLCIYDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  37
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  150
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N-benzyloxycarbonyl-O-(4-O-chloroacetyl-β-D-xylopyranosyl)-L-serine benzyl ester 在 palladium on activated charcoal 四氮唑 、 氢气 、 溶剂黄146 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 97.5h， 生成 O-(2-O-phosphono-β-D-xylopyranosyl)-L-serine trisodium salt
  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 在 吡啶 、 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 乙酸肼 、 二正丁基氧化锡 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 9.5h， 生成 N-benzyloxycarbonyl-O-(4-O-chloroacetyl-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

文献信息

• Stereoselective syntheses of phosphorylated and sulfated glycosyl serines in glycosaminoglycan for biological probes
  作者：Jun-ichi Tamura、Junko Nishihara

  DOI：10.1016/s0960-894x(99)00300-5

  日期：1999.7

  Phosphorylated glycosyl serines of glycosaminoglycan with/without sulfate: beta-D-Xyl(2P)-Ser (1) and beta-D-Gal(+/-6S)-(1-->4)-beta-D-Xyl(2P)-Ser (2, 3) were suitably designed for biological probes. These oligosaccharides were synthesized in a stereocontrolled manner. (C) 1999 Elsevier Science Ltd. All rights reserved.
• 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.