{(2S,3R,4R,5S,6R)-2-[tert-Butyl-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-decyloxy)-phenyl-silanyloxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-carbamic acid 2,2,2-trichloro-ethyl ester | 807355-17-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: {(2S,3R,4R,5S,6R)-2-[tert-Butyl-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-decyloxy)-phenyl-silanyloxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-carbamic acid 2,2,2-trichloro-ethyl ester
• CAS: 807355-17-5
• 化学式: C₂₉H₃₁Cl₃F₁₇NO₈Si
• 分子量: 978.984
• InChiKey: ULKWUKQCJOTEJD-DQWQIEKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.47
• 重原子数：
  59.0
• 可旋转键数：
  16.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  126.71
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  苯甲醛二甲缩醛 、 {(2S,3R,4R,5S,6R)-2-[tert-Butyl-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-decyloxy)-phenyl-silanyloxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-carbamic acid 2,2,2-trichloro-ethyl ester 在 camphor-10-sulfonic acid 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以0.885 g的产率得到{(2R,4aR,6S,7R,8R,8aS)-6-[tert-Butyl-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-decyloxy)-phenyl-silanyloxy]-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-carbamic acid 2,2,2-trichloro-ethyl ester
  参考文献：
  名称：

  Synthesis of the Lewis a Trisaccharide Based on an Anomeric Silyl Fluorous Tag

  摘要：

  The synthesis of the trisaccharide Lewis a was performed using an anomeric fluorous silyl protective group. This methodology allowed us to fully characterize each product (NMR, MS) and monitor each synthetic step (TLC). Although the product purifications could be performed by fluorous-solid-phase extraction (F-SPE) technology, standard chromatography could be used to effect purification if necessary. Trichloroethoxy carbonyl (Troc) protection of the amino group of the glucosamine moiety was found essential to allow protecting group manipulation of the fluorous protected sugar.

  DOI：

  10.1021/ol048474g
• 作为产物：
  描述：

  Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-[tert-butyl-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-decyloxy)-phenyl-silanyloxy]-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 {(2S,3R,4R,5S,6R)-2-[tert-Butyl-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-decyloxy)-phenyl-silanyloxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-carbamic acid 2,2,2-trichloro-ethyl ester
  参考文献：
  名称：

  Synthesis of the Lewis a Trisaccharide Based on an Anomeric Silyl Fluorous Tag

  摘要：

  The synthesis of the trisaccharide Lewis a was performed using an anomeric fluorous silyl protective group. This methodology allowed us to fully characterize each product (NMR, MS) and monitor each synthetic step (TLC). Although the product purifications could be performed by fluorous-solid-phase extraction (F-SPE) technology, standard chromatography could be used to effect purification if necessary. Trichloroethoxy carbonyl (Troc) protection of the amino group of the glucosamine moiety was found essential to allow protecting group manipulation of the fluorous protected sugar.

  DOI：

  10.1021/ol048474g