(2R,3S,4R)-4-Benzyloxy-2-benzyloxymethyl-3-[(2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-3,4-dihydro-2H-pyran | 895140-72-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4R)-4-Benzyloxy-2-benzyloxymethyl-3-[(2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-3,4-dihydro-2H-pyran
• CAS: 895140-72-4
• 化学式: C₇₄H₇₈O₁₃
• 分子量: 1175.43
• InChiKey: UBNWFRSZLJHLJD-RLNOSZOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.08
• 重原子数：
  87.0
• 可旋转键数：
  30.0
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  119.99
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  2-(三甲基硅基)乙磺酰胺 、 (2R,3S,4R)-4-Benzyloxy-2-benzyloxymethyl-3-[(2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-3,4-dihydro-2H-pyran 在 iodonium(di-γ-collidine) perchlorate 作用下， 以 二氯甲烷 为溶剂， 反应 1.33h， 生成
  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：

  (3aS,4R,6S,7R,7aS)-6-((2R,3S,4R)-4-Benzyloxy-2-benzyloxymethyl-3,4-dihydro-2H-pyran-3-yloxy)-4-hydroxymethyl-7-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-one 在 sodium hydride 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.5h， 生成 (2R,3S,4R)-4-Benzyloxy-2-benzyloxymethyl-3-[(2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-3,4-dihydro-2H-pyran
  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