phenyl 4,6-O-di(tert-butyl)silylidene-1,2-dideoxy-3-O-levulinoyl-2-trichloroacetamido-1-thio-β-D-glucopyranoside | 1158796-90-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: phenyl 4,6-O-di(tert-butyl)silylidene-1,2-dideoxy-3-O-levulinoyl-2-trichloroacetamido-1-thio-β-D-glucopyranoside
• 英文别名: [(4aR,6S,7R,8R,8aS)-2,2-ditert-butyl-6-phenylsulfanyl-7-[(2,2,2-trichloroacetyl)amino]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-8-yl] 4-oxopentanoate
• CAS: 1158796-90-7
• 化学式: C₂₇H₃₈Cl₃NO₇SSi
• 分子量: 655.112
• InChiKey: CACDARLIBDQDRU-KNQBKSORSA-N

物化性质

• 沸点：
  685.7±55.0 °C(predicted)
• 密度：
  1.29±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  126
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  phenyl 4,6-O-di(tert-butyl)silylidene-1,2-dideoxy-3-O-levulinoyl-2-trichloroacetamido-1-thio-β-D-glucopyranoside 、 methyl (phenyl 2,3-di-O-benzoyl-1-thio-β-D-glucopyranosid)uronate 在 三氟甲磺酸酐 、 二苯基亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以70%的产率得到methyl (phenyl 2,3-di-O-benzoyl-4-[4,6-O-di-tert-butylsilylidene-3-O-levulinoyl-2-N-trichloroacetamido-β-D-glucopyranosyl]-1-thio-β-D-glucopyranosyl uronate)
  参考文献：
  名称：

  Synthesis of Hyaluronic Acid Oligomers using Chemoselective and One-Pot Strategies

  摘要：

  An efficient synthetic strategy toward a hyaluronic acid (HA) tri-, penta-, and heptamer having a glucosamine-reducing end is reported. The synthesis is based on a glucuronate ester thioglycoside and a trifluoro-N-phenylimidate glucosamine building block. The HA-fragments are synthesized using an S-phenyl GlcN-GluA building block through a combination of chemoselective and one-pot condensation strategies.

  DOI：

  10.1021/jo9003713
• 作为产物：
  描述：

  phenyl 4,6-O-di(tert-butyl)silylidene-1,2-dideoxy-2-trichloroacetamido-1-thio-β-D-glucopyranoside 、 乙酰丙酸 在 4-二甲氨基吡啶 、 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到phenyl 4,6-O-di(tert-butyl)silylidene-1,2-dideoxy-3-O-levulinoyl-2-trichloroacetamido-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Hyaluronic Acid Oligomers using Chemoselective and One-Pot Strategies

  摘要：

  An efficient synthetic strategy toward a hyaluronic acid (HA) tri-, penta-, and heptamer having a glucosamine-reducing end is reported. The synthesis is based on a glucuronate ester thioglycoside and a trifluoro-N-phenylimidate glucosamine building block. The HA-fragments are synthesized using an S-phenyl GlcN-GluA building block through a combination of chemoselective and one-pot condensation strategies.

  DOI：

  10.1021/jo9003713

文献信息

• Synthesis of Hyaluronic Acid Oligomers using Chemoselective and One-Pot Strategies
  作者：Jasper Dinkelaar、Henrik Gold、Herman S. Overkleeft、Jeroen D. C. Codée、Gijsbert A. van der Marel

  DOI：10.1021/jo9003713

  日期：2009.6.5

  An efficient synthetic strategy toward a hyaluronic acid (HA) tri-, penta-, and heptamer having a glucosamine-reducing end is reported. The synthesis is based on a glucuronate ester thioglycoside and a trifluoro-N-phenylimidate glucosamine building block. The HA-fragments are synthesized using an S-phenyl GlcN-GluA building block through a combination of chemoselective and one-pot condensation strategies.