4-O-(3-O-allyl-β-D-galactopyranosyl)-D-arabino-hex-1-enitol | 132911-84-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-O-(3-O-allyl-β-D-galactopyranosyl)-D-arabino-hex-1-enitol
• 英文别名: (2S,3R,4S,5S,6R)-2-[[(2R,3S,4R)-4-hydroxy-2-(hydroxymethyl)-3,4-dihydro-2H-pyran-3-yl]oxy]-6-(hydroxymethyl)-4-prop-2-enoxyoxane-3,5-diol
• CAS: 132911-84-3
• 化学式: C₁₅H₂₄O₉
• 分子量: 348.35
• InChiKey: KFHCGJPBJMFBFP-AMTOUNBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  138
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-O-(3-O-allyl-β-D-galactopyranosyl)-D-arabino-hex-1-enitol 在 Rhodium, chlorobis(triphenylphosphine)- 吡啶 、 三乙烯二胺 、 sodium hydride 、 cesium fluoride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 246.25h， 生成 2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((2S,3R,4S,5R,6R)-3,5-bis-benzyloxy-6-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-2-yloxy)-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione
  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：

  hexa-O-acetyl-D-lactal 在 氨 、 二正丁基氧化锡 作用下， 以 甲醇 、 苯 为溶剂， 生成 4-O-(3-O-allyl-β-D-galactopyranosyl)-D-arabino-hex-1-enitol
  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

• Schaubach, Regine; Hemberger, Juergen; Kinzy, Willy, Liebigs Annalen der Chemie, 1991, # 7, p. 607 - 614
  作者：Schaubach, Regine、Hemberger, Juergen、Kinzy, Willy

  DOI：——

  日期：——
• SCHAUBACH, REGINE;HEMBERGER, JURGEN;KINZY, WILLY, LIEBIGS ANN. CHEM.,(1991) N, C. 607-614
  作者：SCHAUBACH, REGINE、HEMBERGER, JURGEN、KINZY, WILLY

  DOI：——

  日期：——
• 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.