Man(a1-3)[Man(a1-6)]Man(b1-4)GlcNAc(b1-4)GlcNAc(b)-SEt | 312967-40-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Man(a1-3)[Man(a1-6)]Man(b1-4)GlcNAc(b1-4)GlcNAc(b)-SEt
• 英文别名: N-[(2S,3R,4R,5S,6R)-2-[(2R,3S,4R,5R,6S)-5-acetamido-6-ethylsulfanyl-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-5-[(2S,3S,4S,5R,6R)-3,5-dihydroxy-4-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 312967-40-1
• 化学式: C₃₆H₆₂N₂O₂₅S
• 分子量: 954.953
• InChiKey: SSGNNSVARNTTIF-KWFOLVMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8.9
• 重原子数：
  64
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  450
• 氢给体数：
  16
• 氢受体数：
  26

反应信息

• 作为反应物：
  描述：

  Man(a1-3)[Man(a1-6)]Man(b1-4)GlcNAc(b1-4)GlcNAc(b)-SEt 在 碳酸氢铵 、 calcium carbonate 、 mercury dichloride 作用下， 以 水 为溶剂， 反应 19.0h， 生成 Man(a1-3)[Man(a1-6)]Man(b1-4)GlcNAc(b1-4)b-GlcNAc1N
  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：

  在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 15.0h， 以86%的产率得到Man(a1-3)[Man(a1-6)]Man(b1-4)GlcNAc(b1-4)GlcNAc(b)-SEt
  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

• From Glycals to Glycopeptides: A Convergent and Stereoselective Total Synthesis of a High Mannose N-Linked Glycopeptide
  作者：Zhi-Guang Wang、XuFang Zhang、David Live、Samuel J. Danishefsky

  DOI：10.1002/1521-3773(20001016)39:20<3652::aid-anie3652>3.0.co;2-b

  日期：2000.10.16
• A highly convergent synthesis of an N-linked glycopeptide presenting the H-type 2 human blood group determinant
  作者：Zhi-Guang Wang、J. David Warren、Vadim Y. Dudkin、Xufang Zhang、Ulrich Iserloh、Michael Visser、Matthias Eckhardt、Peter H. Seeberger、Samuel J. Danishefsky

  DOI：10.1016/j.tet.2006.02.080

  日期：2006.5

  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.