prop-2-enyl (2S)-3-[(2S,3R,4R,5R,6R)-3-azido-5-hydroxy-6-(hydroxymethyl)-4-phenylmethoxyoxan-2-yl]oxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoate | 146936-87-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: prop-2-enyl (2S)-3-[(2S,3R,4R,5R,6R)-3-azido-5-hydroxy-6-(hydroxymethyl)-4-phenylmethoxyoxan-2-yl]oxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoate
• CAS: 146936-87-0
• 化学式: C₃₄H₃₆N₄O₉
• 分子量: 644.681
• InChiKey: PQUGBECLOMXKSW-MBWHCWHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  47
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  147
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (3S,4R,5S,6R)-5-Acetylamino-4-benzyloxy-2-bromo-3-phenylsulfanyl-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid benzyl ester 、 prop-2-enyl (2S)-3-[(2S,3R,4R,5R,6R)-3-azido-5-hydroxy-6-(hydroxymethyl)-4-phenylmethoxyoxan-2-yl]oxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoate 在 氰化汞 、 mercury dibromide 作用下， 以 四氯化碳 为溶剂， 以66%的产率得到
  参考文献：
  名称：

  Synthesis of the N-terminal glycopentapeptides of human glycophorin am and an carrying trimeric sialosyl Tn epitope

  摘要：

  Pentapeptides with a cluster of sialosyl Tn epitopes, designed as models for MN blood group antigenic determinants of human glycophorin A, were synthesized in a stereocontrolled manner.

  DOI：

  10.1016/s0040-4039(00)74775-7
• 作为产物：
  描述：

  N-(9-fluorenylmethoxycarbonyl)-L-serine allyl ester 在 二氯二茂锆 silver perchlorate 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 生成 prop-2-enyl (2S)-3-[(2S,3R,4R,5R,6R)-3-azido-5-hydroxy-6-(hydroxymethyl)-4-phenylmethoxyoxan-2-yl]oxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoate
  参考文献：
  名称：

  Synthesis of the N-terminal glycopentapeptides of human glycophorin am and an carrying trimeric sialosyl Tn epitope

  摘要：

  Pentapeptides with a cluster of sialosyl Tn epitopes, designed as models for MN blood group antigenic determinants of human glycophorin A, were synthesized in a stereocontrolled manner.

  DOI：

  10.1016/s0040-4039(00)74775-7

文献信息

• Solid-phase synthesis of core 3 and core 6 O-glycan-linked glycopeptides by benzyl-protection method
  作者：Yuko Nakahara、Chinatsu Ozawa、Eriko Tanaka、Kazuki Ohtsuka、Yutaka Takano、Hironobu Hojo、Yoshiaki Nakahara

  DOI：10.1016/j.tet.2006.12.087

  日期：2007.3

  Core 3 and core 6 O-glycoamino acids were prepared in a protected form suited for Fmoc solid-phase peptide synthesis (SPPS). An N-trichloroacetyllactosamine derivative (2) was used as a highly beta-selective glycosyl donor in 3-O-glycosylation of acceptors 314 and in 6-O-glycosylation of acceptors 5/6. Zn reduction of trisaccharides 7/8 and 13/14 was followed by acetylation to readily transform trichloroacetamido and azido groups to acetamido groups. Selective deprotection by Pd(0)-catalysis afforded core 3 O-glycan building blocks 11/12 and core 6 O-glycan building blocks 17/18. Usefulness of these building blocks for SPPS was demonstrated by the syntheses of the core 3-linked MUC2 tandem repeat glycopeptide and the core 6-linked glycopeptide segment of MUC6. The synthetic glycopeptides detached from the resin were debenzylated under the 'low-acidity TfOH' conditions. (c) 2007 Elsevier Ltd. All rights reserved.