Nα-fluorenylmethoxycarbonyl-trans-4-hydroxy-4-O-[(2,3,4,6-tetra-O-benzoyl)-α-D-mannopyranosyl]-L-proline allyl ester | 1000384-03-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Nα-fluorenylmethoxycarbonyl-trans-4-hydroxy-4-O-[(2,3,4,6-tetra-O-benzoyl)-α-D-mannopyranosyl]-L-proline allyl ester
• 英文别名: 1-O-(9H-fluoren-9-ylmethyl) 2-O-prop-2-enyl (2S,4R)-4-[(2S,3S,4S,5R,6R)-3,4,5-tribenzoyloxy-6-(benzoyloxymethyl)oxan-2-yl]oxypyrrolidine-1,2-dicarboxylate
• CAS: 1000384-03-1
• 化学式: C₅₇H₄₉NO₁₄
• 分子量: 972.014
• InChiKey: JUQJOLWOXAQEMX-BDPNHYCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  72
• 可旋转键数：
  22
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  180
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  Nα-fluorenylmethoxycarbonyl-trans-4-hydroxy-4-O-[(2,3,4,6-tetra-O-benzoyl)-α-D-mannopyranosyl]-L-proline allyl ester 在 四(三苯基膦)钯 苯硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以50%的产率得到Nα-fluorenylmethoxycarbonyl-trans-4-hydroxy-4-O-[(2,3,4,6-tetra-O-benzoyl)-α-D-mannopyranosyl]-L-proline
  参考文献：
  名称：

  A comparative study of different glycosylation methods for the synthesis of d-mannopyranosides of Nα-fluorenylmethoxycarbonyl-trans-4-hydroxy-l-proline allyl ester

  摘要：

  The synthesis of N alpha-fluorenylmethoxycarbonyl-trans-4-hydroxy-4-O[(2,3,4,6-tetra-O-acetyl)-alpha-D-mannopyranosyl]-L-proline allyl ester and N alpha-fluorenylmethoxycarbonyl- trans-4-hydroxy-4- O-[(2,3,4,6-tetra- O-benzoyl) -alpha-D -mannopyranosyl]-L -proline allyl ester is described. Glycosylation using Konigs-Knorr conditions with a benzoyl protected glycosyl donor provided the optimum method. Removal of the allyl ester gave two mannosylated building blocks suitable for solid phase glycopeptide synthesis. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.08.015
• 作为产物：
  描述：

  [(2R,3R,4S,5S,6S)-3,4,5-三苯甲酰氧基-6-(2,2,2-三氯亚氨代乙酰)氧基-四氢吡喃-2-基]甲基苯甲酸酯 、 Nα-fluorenylmethoxycarbonyl-trans-4-hydroxy-L-proline allyl ester 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以73%的产率得到Nα-fluorenylmethoxycarbonyl-trans-4-hydroxy-4-O-[(2,3,4,6-tetra-O-benzoyl)-α-D-mannopyranosyl]-L-proline allyl ester
  参考文献：
  名称：

  A comparative study of different glycosylation methods for the synthesis of d-mannopyranosides of Nα-fluorenylmethoxycarbonyl-trans-4-hydroxy-l-proline allyl ester

  摘要：

  The synthesis of N alpha-fluorenylmethoxycarbonyl-trans-4-hydroxy-4-O[(2,3,4,6-tetra-O-acetyl)-alpha-D-mannopyranosyl]-L-proline allyl ester and N alpha-fluorenylmethoxycarbonyl- trans-4-hydroxy-4- O-[(2,3,4,6-tetra- O-benzoyl) -alpha-D -mannopyranosyl]-L -proline allyl ester is described. Glycosylation using Konigs-Knorr conditions with a benzoyl protected glycosyl donor provided the optimum method. Removal of the allyl ester gave two mannosylated building blocks suitable for solid phase glycopeptide synthesis. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.08.015

文献信息

• A comparative study of different glycosylation methods for the synthesis of d-mannopyranosides of Nα-fluorenylmethoxycarbonyl-trans-4-hydroxy-l-proline allyl ester
  作者：Dong Jun Lee、Renata Kowalczyk、Victoria J. Muir、Phillip M. Rendle、Margaret A. Brimble

  DOI：10.1016/j.carres.2007.08.015

  日期：2007.12

  The synthesis of N alpha-fluorenylmethoxycarbonyl-trans-4-hydroxy-4-O[(2,3,4,6-tetra-O-acetyl)-alpha-D-mannopyranosyl]-L-proline allyl ester and N alpha-fluorenylmethoxycarbonyl- trans-4-hydroxy-4- O-[(2,3,4,6-tetra- O-benzoyl) -alpha-D -mannopyranosyl]-L -proline allyl ester is described. Glycosylation using Konigs-Knorr conditions with a benzoyl protected glycosyl donor provided the optimum method. Removal of the allyl ester gave two mannosylated building blocks suitable for solid phase glycopeptide synthesis. (c) 2007 Elsevier Ltd. All rights reserved.