N-benzyloxycarbonyl-O-{O-[(2,3,4-tri-O-4-methylbenzoyl)-β-D-galactopyranosyl]-(1->3)-O-(2-O-acetyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1->4)-(3-O-acetyl-2-O-dibenzyloxyphosphinyl-β-D-xylopyranosyl)}-L-serine benzyl ester | 343254-50-2

• 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-{O-[(2,3,4-tri-O-4-methylbenzoyl)-β-D-galactopyranosyl]-(1->3)-O-(2-O-acetyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1->4)-(3-O-acetyl-2-O-dibenzyloxyphosphinyl-β-D-xylopyranosyl)}-L-serine benzyl ester
• 英文别名: [(2R,3S,4S,5R,6S)-6-[[(2S,4aR,6S,7R,8S,8aS)-7-acetyloxy-6-[(3R,4S,5R,6R)-4-acetyloxy-5-bis(phenylmethoxy)phosphoryloxy-6-[(2S)-3-oxo-3-phenylmethoxy-2-(phenylmethoxycarbonylamino)propoxy]oxan-3-yl]oxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]-2-(hydroxymethyl)-4,5-bis[(4-methylbenzoyl)oxy]oxan-3-yl] 4-methylbenzoate
• CAS: 343254-50-2
• 化学式: C₈₄H₈₆NO₂₇P
• 分子量: 1572.57
• InChiKey: QHANGUPNRXLLMT-PJDPZWMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.8
• 重原子数：
  113
• 可旋转键数：
  38
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  335
• 氢给体数：
  2
• 氢受体数：
  27

反应信息

• 作为反应物：
  描述：

  N-benzyloxycarbonyl-O-{O-[(2,3,4-tri-O-4-methylbenzoyl)-β-D-galactopyranosyl]-(1->3)-O-(2-O-acetyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1->4)-(3-O-acetyl-2-O-dibenzyloxyphosphinyl-β-D-xylopyranosyl)}-L-serine benzyl ester 在 palladium on activated charcoal 氢气 、 溶剂黄146 、 三乙胺 、 AG₅₀₀W-X₈ (Na⁺) 作用下， 以 甲醇 、 水 为溶剂， 反应 124.5h， 以49%的产率得到O-[O-β-D-galactopyranosyl-(1->3)-O-β-D-galactopyranosyl-(1->4)-(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：

  在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 以12.3 mg的产率得到N-benzyloxycarbonyl-O-{O-[(2,3,4-tri-O-4-methylbenzoyl-α-D-galactopyranosyl)-(1->3)-O-(2-O-acetyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1->4)-(3-O-acetyl-2-O-dibenzyloxyphosphinyl-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