4-nitrophenyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1-> 4)-2-acetamido-6-O-tert-butyldiphenylsilyl-2-deoxy-1-thio-β-D-glucopyranoside | 249552-07-6

• 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: 4-nitrophenyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1-> 4)-2-acetamido-6-O-tert-butyldiphenylsilyl-2-deoxy-1-thio-β-D-glucopyranoside
• 英文别名: [(2R,3S,4S,5R,6S)-3,4,5-tribenzoyloxy-6-[(2R,3S,4R,5R,6S)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-5-(1,3-dioxoisoindol-2-yl)-4-hydroxy-6-(4-nitrophenyl)sulfanyloxan-3-yl]oxyoxan-2-yl]methyl benzoate
• CAS: 249552-07-6
• 化学式: C₇₀H₆₂N₂O₁₇SSi
• 分子量: 1263.42
• InChiKey: RIJNMPJPXRAHAA-ANMIHUJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.66
• 重原子数：
  91
• 可旋转键数：
  24
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  271
• 氢给体数：
  1
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  苯基-2,3,4-三-O-苄基-1-硫代-β-L-岩藻吡喃糖苷 、 4-nitrophenyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1-> 4)-2-acetamido-6-O-tert-butyldiphenylsilyl-2-deoxy-1-thio-β-D-glucopyranoside 在 DMTST 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 1.0h， 以72%的产率得到4-nitrophenyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1-> 4)-[2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1-> 3)]-2-phthalimido-6-O-tert-butyldiphenylsilyl-2-deoxy-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Active–latent glycosylation strategy toward Lewis X pentasaccharide in a form suitable for neoglycoconjugate syntheses

  摘要：

  Glycosylation of 4-nitrophenyl 2-acetamido-6-O-tert-butyldiphenylsilyl-2-deoxy-1-thio-beta-D-glucopyranoside with phenyl 2,3,4,6-tetra-O-benzoyl-1-thio-beta-D-galactopyranoside in the presence of NIS and TfOH as catalyst gave the lactosamine derivative regiospecifically in high yield. Further 3-O-fucosylation with phenyl 2,3,4-tri-O-benzyl-1-thio-beta-L-fucopyranoside using DMTST as promoter afforded the Le(x) trisaccharide intermediate. The latent glycosyl donor was transformed into its active form (p-acetamidothiophenyl) by reduction with zinc in acetic acid and N-acetylation. Glycosidation with p-nitrothiophenyl lactoside acceptor in the presence of NIS/TfOH as catalyst gave the Le(x) pentasaccharide in 71% yield. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00080-4
• 作为产物：
  描述：

  叔丁基二苯基氯硅烷 在 吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.92h， 生成 4-nitrophenyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1-> 4)-2-acetamido-6-O-tert-butyldiphenylsilyl-2-deoxy-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Active–latent glycosylation strategy toward Lewis X pentasaccharide in a form suitable for neoglycoconjugate syntheses

  摘要：

  Glycosylation of 4-nitrophenyl 2-acetamido-6-O-tert-butyldiphenylsilyl-2-deoxy-1-thio-beta-D-glucopyranoside with phenyl 2,3,4,6-tetra-O-benzoyl-1-thio-beta-D-galactopyranoside in the presence of NIS and TfOH as catalyst gave the lactosamine derivative regiospecifically in high yield. Further 3-O-fucosylation with phenyl 2,3,4-tri-O-benzyl-1-thio-beta-L-fucopyranoside using DMTST as promoter afforded the Le(x) trisaccharide intermediate. The latent glycosyl donor was transformed into its active form (p-acetamidothiophenyl) by reduction with zinc in acetic acid and N-acetylation. Glycosidation with p-nitrothiophenyl lactoside acceptor in the presence of NIS/TfOH as catalyst gave the Le(x) pentasaccharide in 71% yield. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00080-4

文献信息

• Active–latent glycosylation strategy toward Lewis X pentasaccharide in a form suitable for neoglycoconjugate syntheses
  作者：Suoding Cao、Zhonghong Gan、René Roy

  DOI：10.1016/s0008-6215(99)00080-4

  日期：1999.5

  Glycosylation of 4-nitrophenyl 2-acetamido-6-O-tert-butyldiphenylsilyl-2-deoxy-1-thio-beta-D-glucopyranoside with phenyl 2,3,4,6-tetra-O-benzoyl-1-thio-beta-D-galactopyranoside in the presence of NIS and TfOH as catalyst gave the lactosamine derivative regiospecifically in high yield. Further 3-O-fucosylation with phenyl 2,3,4-tri-O-benzyl-1-thio-beta-L-fucopyranoside using DMTST as promoter afforded the Le(x) trisaccharide intermediate. The latent glycosyl donor was transformed into its active form (p-acetamidothiophenyl) by reduction with zinc in acetic acid and N-acetylation. Glycosidation with p-nitrothiophenyl lactoside acceptor in the presence of NIS/TfOH as catalyst gave the Le(x) pentasaccharide in 71% yield. (C) 1999 Elsevier Science Ltd. All rights reserved.