1,4-Dideoxy-2,3:5,6-di-O-isopropylidene-1,4-imino-L-talitol | 129312-28-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,4-Dideoxy-2,3:5,6-di-O-isopropylidene-1,4-imino-L-talitol
• 英文别名: 1,4-dideoxy-2,3;5,6-di-O-isopropylidene-1,4-imino-D-allitol；(3aR,4R,6aS)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole
• CAS: 129312-28-3
• 化学式: C₁₂H₂₁NO₄
• 分子量: 243.303
• InChiKey: OLPCNFRAOMKWMK-QEYWKRMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.63
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  48.95
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1,4-Dideoxy-2,3:5,6-di-O-isopropylidene-1,4-imino-L-talitol 在 盐酸 、 三乙胺 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 17.5h， 生成 N-fluorenylmethoxycarbonyl-1,4-dideoxy-2,3-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
• 作为产物：
  描述：

  在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以88%的产率得到1,4-Dideoxy-2,3:5,6-di-O-isopropylidene-1,4-imino-L-talitol
  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

• Buchanan, J. Grant; Lumbard, Keith W.; Sturgeon, Robert J., Journal of the Chemical Society. Perkin transactions I, 1990, p. 699 - 706
  作者：Buchanan, J. Grant、Lumbard, Keith W.、Sturgeon, Robert J.、Thompson, Deryk K.

  DOI：——

  日期：——
• BUCHANAN, J. GRANT;LUMBARD, KEITH W.;STURGEON, ROBERT J.;THOMPSON, DERYK +, J. CHEM. SOC. PERKIN TRANS. PT 1,(1990) N, C. 699-706
  作者：BUCHANAN, J. GRANT、LUMBARD, KEITH W.、STURGEON, ROBERT J.、THOMPSON, DERYK +

  DOI：——

  日期：——