N-fluorenylmethoxycarbonyl-1,4-dideoxy-2,3;5,6-di-O-isopropylidene-1,4-imino-D-allitol | 221451-08-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N-fluorenylmethoxycarbonyl-1,4-dideoxy-2,3;5,6-di-O-isopropylidene-1,4-imino-D-allitol
• 英文别名: 9H-fluoren-9-ylmethyl (3aR,4R,6aS)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate
• CAS: 221451-08-7
• 化学式: C₂₇H₃₁NO₆
• 分子量: 465.546
• InChiKey: CJXJSSKUFWSUKY-XQUALCHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  66.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-fluorenylmethoxycarbonyl-1,4-dideoxy-2,3;5,6-di-O-isopropylidene-1,4-imino-D-allitol 在 盐酸 、 sodium periodate 作用下， 以 乙醇 、 水 为溶剂， 反应 2.75h， 生成
  参考文献：
  名称：

  Synthesis of l-2,3-trans-3,4-cis-Dihydroxyproline Building Blocks for Peptide Synthesis

  摘要：

  L-2,3-trans-3,4-cis-N-Fluorenylmethoxycarbonyl-3,4-dihydroxy-3,4-O-isopropylidineproline (9) has been prepared from D-gulonolactone in nine steps and an overall yield of 22%. Compound 9 has been converted to its allyl ester 13. Compounds 9 and 13 were investigated as building blocks for the incorporation of dihydroxyproline into peptides, with compound 9 serving as a carboxyl component and compound 13 as a precursor to an amino component for peptide coupling reactions. Their utility was demonstrated by the synthesis of dipeptides 11 and 15.

  DOI：

  10.1021/jo982009d
• 作为产物：
  描述：

  在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 15.0h， 生成 N-fluorenylmethoxycarbonyl-1,4-dideoxy-2,3;5,6-di-O-isopropylidene-1,4-imino-D-allitol
  参考文献：
  名称：

  Synthesis of l-2,3-trans-3,4-cis-Dihydroxyproline Building Blocks for Peptide Synthesis

  摘要：

  L-2,3-trans-3,4-cis-N-Fluorenylmethoxycarbonyl-3,4-dihydroxy-3,4-O-isopropylidineproline (9) has been prepared from D-gulonolactone in nine steps and an overall yield of 22%. Compound 9 has been converted to its allyl ester 13. Compounds 9 and 13 were investigated as building blocks for the incorporation of dihydroxyproline into peptides, with compound 9 serving as a carboxyl component and compound 13 as a precursor to an amino component for peptide coupling reactions. Their utility was demonstrated by the synthesis of dipeptides 11 and 15.

  DOI：

  10.1021/jo982009d

文献信息

• Synthesis of <scp>l</scp>-2,3-<i>trans</i>-3,4-<i>cis-</i>Dihydroxyproline Building Blocks for Peptide Synthesis
  作者：Claudette A. Weir、Carol M. Taylor

  DOI：10.1021/jo982009d

  日期：1999.3.1

  L-2,3-trans-3,4-cis-N-Fluorenylmethoxycarbonyl-3,4-dihydroxy-3,4-O-isopropylidineproline (9) has been prepared from D-gulonolactone in nine steps and an overall yield of 22%. Compound 9 has been converted to its allyl ester 13. Compounds 9 and 13 were investigated as building blocks for the incorporation of dihydroxyproline into peptides, with compound 9 serving as a carboxyl component and compound 13 as a precursor to an amino component for peptide coupling reactions. Their utility was demonstrated by the synthesis of dipeptides 11 and 15.