N-[(2S,3R,4R,5S,6R)-2-Benzyloxy-5-[(2S,3R,4R,5S)-5-((R)-1,2-dihydroxy-ethyl)-3,4-dihydroxy-tetrahydro-furan-2-yloxy]-4-hydroxy-6-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl]-acetamide | 206649-93-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[(2S,3R,4R,5S,6R)-2-Benzyloxy-5-[(2S,3R,4R,5S)-5-((R)-1,2-dihydroxy-ethyl)-3,4-dihydroxy-tetrahydro-furan-2-yloxy]-4-hydroxy-6-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl]-acetamide
• CAS: 206649-93-6
• 化学式: C₂₇H₄₁NO₁₆
• 分子量: 635.62
• InChiKey: AOZJIJAPXVCUTG-CCZMOAHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.2
• 重原子数：
  44.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  266.55
• 氢给体数：
  10.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  N-[(2S,3R,4R,5S,6R)-2-Benzyloxy-5-[(2S,3R,4R,5S)-5-((R)-1,2-dihydroxy-ethyl)-3,4-dihydroxy-tetrahydro-furan-2-yloxy]-4-hydroxy-6-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl]-acetamide 在 palladium on activated charcoal ammonium formate 作用下， 以 甲醇 为溶剂， 反应 0.33h， 生成 N-[(2R,3R,4R,5S,6R)-5-[(2S,3R,4R,5S)-5-((R)-1,2-Dihydroxy-ethyl)-3,4-dihydroxy-tetrahydro-furan-2-yloxy]-2,4-dihydroxy-6-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl]-acetamide 、 N-[(2S,3R,4R,5S,6R)-5-[(2S,3R,4R,5S)-5-((R)-1,2-Dihydroxy-ethyl)-3,4-dihydroxy-tetrahydro-furan-2-yloxy]-2,4-dihydroxy-6-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl]-acetamide
  参考文献：
  名称：

  One-pot synthesis of β-d-Gal>(1 → 4)[β-d-Galp(1 → 6)]-d-GlcNAc, a ‘core’ trisaccharide linked O-glycosidically in glycoproteins of Trypanosoma cruzi

  摘要：

  Tin(IV) chloride-promoted condensation of benzyl 2-acetamido-3-O-benzoyl-2-deoxy-alpha-D-glucopyranoside (4) with penta-O-benzoyl-beta-D-galactopyranose (6) gave the derivative of beta-D-Galp-(1 --> 6)-alpha-D-GlcNAc 7 in 80% yield, This was glycosylated with penta-O-benzoyl-alpha,beta- D-galactofuranose (5>, employing the same catalyst, to afford the protected benzyl per-O-benzoyl-beta-D-Galf(1 --> 4)[beta-D-Galp(1 --> 6)]D-GlcNAc 10 in 41% yield, Alternatively, compound 10 was obtained directly in a one-pot reaction from 4, by sequential addition of 6 and 5 (34% yield). beta-Glycosidic linkages were diastereoselectively formed. De-O-benzoylation of 10, followed by heterogeneous catalytic transfer hydrogenolysis of the benzyl group afforded the free trisaccharide beta-D-Galf(1 --> 4)[beta-D-Galp(1 --> 6)]-D-GlcNAc (14) in 98% yield from 10. Sodium borohydride reduction of 14 gave the corresponding alditol, whose spectral data were identical to those reported for the alditol obtained from the 38-43 kDa cell-surface glycoprotein of Trypanosoma cruzi. (C) 1998 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00256-5
• 作为产物：
  描述：

  benzyl (2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-(1->4)-[2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->6)]-2-acetamido-3-O-benzoyl-2-deoxy-α-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以99%的产率得到N-[(2S,3R,4R,5S,6R)-2-Benzyloxy-5-[(2S,3R,4R,5S)-5-((R)-1,2-dihydroxy-ethyl)-3,4-dihydroxy-tetrahydro-furan-2-yloxy]-4-hydroxy-6-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl]-acetamide
  参考文献：
  名称：

  One-pot synthesis of β-d-Gal>(1 → 4)[β-d-Galp(1 → 6)]-d-GlcNAc, a ‘core’ trisaccharide linked O-glycosidically in glycoproteins of Trypanosoma cruzi

  摘要：

  Tin(IV) chloride-promoted condensation of benzyl 2-acetamido-3-O-benzoyl-2-deoxy-alpha-D-glucopyranoside (4) with penta-O-benzoyl-beta-D-galactopyranose (6) gave the derivative of beta-D-Galp-(1 --> 6)-alpha-D-GlcNAc 7 in 80% yield, This was glycosylated with penta-O-benzoyl-alpha,beta- D-galactofuranose (5>, employing the same catalyst, to afford the protected benzyl per-O-benzoyl-beta-D-Galf(1 --> 4)[beta-D-Galp(1 --> 6)]D-GlcNAc 10 in 41% yield, Alternatively, compound 10 was obtained directly in a one-pot reaction from 4, by sequential addition of 6 and 5 (34% yield). beta-Glycosidic linkages were diastereoselectively formed. De-O-benzoylation of 10, followed by heterogeneous catalytic transfer hydrogenolysis of the benzyl group afforded the free trisaccharide beta-D-Galf(1 --> 4)[beta-D-Galp(1 --> 6)]-D-GlcNAc (14) in 98% yield from 10. Sodium borohydride reduction of 14 gave the corresponding alditol, whose spectral data were identical to those reported for the alditol obtained from the 38-43 kDa cell-surface glycoprotein of Trypanosoma cruzi. (C) 1998 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00256-5