2,3,4-tri-O-acetyl-6-deoxy-6-fluoro-α-D-galactopyranosyl 1-phosphate dibenzyl ester | 153448-94-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4-tri-O-acetyl-6-deoxy-6-fluoro-α-D-galactopyranosyl 1-phosphate dibenzyl ester
• CAS: 153448-94-3
• 化学式: C₂₆H₃₀FO₁₁P
• 分子量: 568.49
• InChiKey: DRLPKGPVOSZATK-RSFKBIFASA-N

物化性质

• 沸点：
  622.7±55.0 °C(predicted)
• 密度：
  1.33±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.03
• 重原子数：
  39.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  132.89
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-acetyl-6-deoxy-6-fluoro-α-D-galactopyranosyl 1-phosphate dibenzyl ester 在 palladium on activated charcoal 氢气 作用下， 生成 uridine 5'-(6-deoxy-6-fluoro-α-D-galactopyranosyl) diphosphate diammonium salt
  参考文献：
  名称：

  Synthesis of UDP-6-deoxy- and -6-fluoro-D-galactoses and their enzymatic glycosyl transfer to mono- and biantennary carbohydrate chains

  摘要：

  Glycosylation with chemicallY prepared UDP-6-deoxy-D-galactose and its 6-fluoro analog using bovine (1-4)-beta-D-galactosyltransferase was demonstrated to be effective enough for practical purpose. A biantennary pentasaccharide having two 6'-deoxylactosamine residues was synthesized.

  DOI：

  10.1016/0040-4039(93)85060-a
• 作为产物：
  描述：

  (2S,3R,4R,5S,6R)-2-((2S,3R,4S,5S,6R)-3,4-Bis-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 在 正丁基锂 、 乙酸肼 作用下， 生成 2,3,4-tri-O-acetyl-6-deoxy-6-fluoro-α-D-galactopyranosyl 1-phosphate dibenzyl ester
  参考文献：
  名称：

  Synthesis of UDP-6-deoxy- and -6-fluoro-D-galactoses and their enzymatic glycosyl transfer to mono- and biantennary carbohydrate chains

  摘要：

  Glycosylation with chemicallY prepared UDP-6-deoxy-D-galactose and its 6-fluoro analog using bovine (1-4)-beta-D-galactosyltransferase was demonstrated to be effective enough for practical purpose. A biantennary pentasaccharide having two 6'-deoxylactosamine residues was synthesized.

  DOI：

  10.1016/0040-4039(93)85060-a

文献信息

• Enzymic transfer of 6-modified d-galactosyl residues: synthesis of biantennary penta- and hepta-saccharides having two 6-deoxy-d-galactose residues at the nonreducing end and evaluation of 6-deoxy-d-galactosyl transfer to glycoprotein using bovine β-(1 → 4)-galactosyltransferase and UDP-6-deoxy-d-galactose
  作者：Yasuhiro Kajihara、Tsuyoshi Endo、Hiroyuki Ogasawara、Hisashi Kodama、Hironobu Hashimoto

  DOI：10.1016/0008-6215(94)00369-q

  日期：1995.4

  UDP-6-Deoxy-D-galactose and UDP-6-deoxy-6-fluoro-D-galactose were synthesized and their transfer to 2-acetamido-2-deoxy-D-glucose (N-acetyl-D-glucosamine) by beta-(1 --> 4)galactosyltransferase was examined. The transfer rates of 6-deoxy-D-galactose and 6-deoxy-6-fluoro-D-galactose were 1.3 and 0.2% of that of D-galactosyl transfer, respectively. The 2-acetamido-4-O-(6-deoxy-beta-D-galactopyranosyl)-2-deoxy-D-glucopyranose (6'-deoxy-N-acetyllactosamine) and methyl 2-acetamido-4-O-(6-deoxy-6-fluoro-beta-D-galactopyranosyl)-2-deoxy-D-glucopyranoside (6'-deoxy-6'-fluoro-N-acetyllactosamine) were synthesized enzymatically in 30 and 59% yields, respectively. Further, 6-deoxy-D-galactose could be completely transferred to N-linked type biantennary oligosaccharides having two N-acetyl-D-glucosaminyl residues at the nonreducing end to give the corresponding penta- and hepta-saccharides in 55 and 57% yields, respectively. An assay of 6-deoxy-D-galactosyl transfer using asialo agalacto alpha(1)-acid glycoprotein as an acceptor suggested that 6-deoxy-D-galactose was transferred to about 30% of the N-acetyl-D-glucosaminyl residues in the N-linked oligosaccharides of the glycoprotein.