N-[(2S,3R,4R,5S,6R)-4-Benzyloxy-2-((2R,3S,4R)-4-benzyloxy-2-benzyloxymethyl-3,4-dihydro-2H-pyran-3-yloxy)-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-3-yl]-benzenesulfonamide | 187879-75-0

• 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)-4-Benzyloxy-2-((2R,3S,4R)-4-benzyloxy-2-benzyloxymethyl-3,4-dihydro-2H-pyran-3-yloxy)-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-3-yl]-benzenesulfonamide
• 英文别名: N-[(2S,3R,4R,5S,6R)-5-hydroxy-4-phenylmethoxy-6-(phenylmethoxymethyl)-2-[[(2R,3S,4R)-4-phenylmethoxy-2-(phenylmethoxymethyl)-3,4-dihydro-2H-pyran-3-yl]oxy]oxan-3-yl]benzenesulfonamide
• CAS: 187879-75-0
• 化学式: C₄₆H₄₉NO₁₀S
• 分子量: 807.962
• InChiKey: FWPYRVAHIUHEIX-ISVAKWLQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  58
• 可旋转键数：
  19
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  139
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  N-[(2S,3R,4R,5S,6R)-4-Benzyloxy-2-((2R,3S,4R)-4-benzyloxy-2-benzyloxymethyl-3,4-dihydro-2H-pyran-3-yloxy)-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-3-yl]-benzenesulfonamide 、 TBDMS(-2)[Bn(-3)][Bn(-4)][Bn(-6)]Man(a1-3)[TBDMS(-2)[Bn(-3)][Bn(-4)][Bn(-6)]Man(a1-6)][Bz(-2)][Mob(-4)]Glc(b)-SEt 在 2,6-二叔丁基吡啶 、 三氟甲烷磺酸甲酯 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以71%的产率得到
  参考文献：
  名称：

  A highly convergent synthesis of an N-linked glycopeptide presenting the H-type 2 human blood group determinant

  摘要：

  The total synthesis of an H-type blood group determinant in a model biological setting is described. The construct is comprised of a high mannose core structure with projecting lactose spacers, culminating in a two-copy presentation of the H-type blood group determinant itself. Key reactions that were used in this construction include sulfonamidohydroxylation (see 15 -> 18) and benzoate-directed glycosylation via an activated thiophenyl donor (see 34 -> 36). Another key strategic element involved the epimerization of an interior core glucoside to reach the P-mannoside (see 37 -> 38) required in the ring C sugar of the high mannose core. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.02.080
• 作为产物：
  描述：

  4-O-Acetyl-3,6-di-O-benzyl-D-glucal 在 2,6-二叔丁基吡啶 、 iodonium(di-γ-collidine) perchlorate 、 三氟甲烷磺酸甲酯 、 lithium hexamethyldisilazane 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-[(2S,3R,4R,5S,6R)-4-Benzyloxy-2-((2R,3S,4R)-4-benzyloxy-2-benzyloxymethyl-3,4-dihydro-2H-pyran-3-yloxy)-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-3-yl]-benzenesulfonamide
  参考文献：
  名称：

  A highly convergent synthesis of an N-linked glycopeptide presenting the H-type 2 human blood group determinant

  摘要：

  The total synthesis of an H-type blood group determinant in a model biological setting is described. The construct is comprised of a high mannose core structure with projecting lactose spacers, culminating in a two-copy presentation of the H-type blood group determinant itself. Key reactions that were used in this construction include sulfonamidohydroxylation (see 15 -> 18) and benzoate-directed glycosylation via an activated thiophenyl donor (see 34 -> 36). Another key strategic element involved the epimerization of an interior core glucoside to reach the P-mannoside (see 37 -> 38) required in the ring C sugar of the high mannose core. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.02.080

文献信息

• Toward Fully Synthetic Homogeneous Glycoproteins: A High Mannose Core Containing Glycopeptide Carrying Full H-Type 2 Human Blood Group Specificity
  作者：Zhi-Guang Wang、Xufang Zhang、Michael Visser、David Live、Andrzej Zatorski、Ulrich Iserloh、Kenneth O. Lloyd、Samuel J. Danishefsky

  DOI：10.1002/1521-3773(20010504)40:9<1728::aid-anie17280>3.0.co;2-1

  日期：2001.5.4
• A Highly Convergent Total Synthetic Route to Glycopeptides Carrying a High-Mannose Core Pentasaccharide DomainN-linked to a Natural Peptide Motif
  作者：Samuel J. Danishefsky、Shuanghua Hu、Pier F. Cirillo、Matthias Eckhardt、Peter H. Seeberger

  DOI：10.1002/chem.19970031011

  日期：1997.10

  AbstractN‐Linked glycopeptides were synthesized by condensation of a highmannose anomeric amine bearing a pentasaccharide with aspartic‐acid‐containing tri‐ and pentapeptides through the agency of IIDQ. The pentasaccharide portion, corresponding to the „core”︁ region of all asparagine‐linked glycoproteins, was assembled by means of glycal‐derived thioethyl donors and glycal acceptors. The central mannose residue was established by inversion of the C2 hydroxyl of a glucosyl precursor in the pentasaccharide. The protecting‐group scheme employed allows the extension of the pentasaccharide through the terminal mannose units. While a fully convergent coupling of the high‐mannose carbohydrate to the peptide domain has thus been accomplished for the first time with a fully synthetic sugar, the stereochemical integrity of the anomeric center of the carbohydrate domain was not maintained and a mixture of glycopeptides was obtained.