O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-2-O-acetyl-6-O-tert-butyldiphenylsilyl-4-O-(4-methylbenzoyl)-D-galactopyranosyl trichloroacetimidate | 343254-46-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-2-O-acetyl-6-O-tert-butyldiphenylsilyl-4-O-(4-methylbenzoyl)-D-galactopyranosyl trichloroacetimidate
• CAS: 343254-46-6
• 化学式: C₄₈H₅₆Cl₃NO₁₇Si
• 分子量: 1053.41
• InChiKey: OVKCAEXCLMIGSI-VTYCQTCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.59
• 重原子数：
  70.0
• 可旋转键数：
  16.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  227.8
• 氢给体数：
  1.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  N-benzyloxycarbonyl-O-(3-O-acetyl-2-O-dibenzyloxyphosphinyl-β-D-xylopyranosyl)-L-serine benzyl ester 、 O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-2-O-acetyl-6-O-tert-butyldiphenylsilyl-4-O-(4-methylbenzoyl)-D-galactopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 、 MS AW₃₀₀ 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以23%的产率得到N-benzyloxycarbonyl-O-{O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->3)-O-[2-O-acetyl-6-O-tert-butyldiphenylsilyl-4-O-(4-methylbenzoyl)-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
• 作为产物：
  描述：

  4-methoxyphenyl 2-O-acetyl-3-O-allyl-6-O-tert-butyldiphenylsilyl-β-D-galactopyranoside 在 (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate 4-二甲氨基吡啶 、 ammonium cerium(IV) nitrate 、 三氟甲磺酸三甲基硅酯 、 MS AW₃₀₀ 、 氢气 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 5.91h， 生成 O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-2-O-acetyl-6-O-tert-butyldiphenylsilyl-4-O-(4-methylbenzoyl)-D-galactopyranosyl trichloroacetimidate
  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