[(2R,3R,4S)-2-((R)-1,2-Dihydroxy-ethyl)-3-methyl-tetrahydro-pyran-4-yl]-carbamic acid 9H-fluoren-9-ylmethyl ester | 192005-39-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: [(2R,3R,4S)-2-((R)-1,2-Dihydroxy-ethyl)-3-methyl-tetrahydro-pyran-4-yl]-carbamic acid 9H-fluoren-9-ylmethyl ester
• 英文别名: 9H-fluoren-9-ylmethyl N-[(2R,3R,4S)-2-[(1R)-1,2-dihydroxyethyl]-3-methyloxan-4-yl]carbamate
• CAS: 192005-39-3
• 化学式: C₂₃H₂₇NO₅
• 分子量: 397.471
• InChiKey: BVNHDCHUGQHJDA-MVMQPQNDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  88
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S)-2-((R)-1,2-Dihydroxy-ethyl)-3-methyl-tetrahydro-pyran-4-yl]-carbamic acid 9H-fluoren-9-ylmethyl ester 在 哌啶 、 Oxone 、 sodium periodate 、 三氟化硼乙醚 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 59.5h， 生成 (2R,3R,4S)-2-[(2R,5R,6S)-6-[(2R,5R,6S)-2-[(2R,3R,4S)-4-amino-3-methyloxan-2-yl]-5-methyl-3,3-dioxo-1,3-oxathian-6-yl]-5-methyl-3,3-dioxo-1,3-oxathian-2-yl]-3-methyloxan-4-amine
  参考文献：
  名称：

  Simple Structural Requirements for Sequence-Selective Peptide Receptors? Tripeptide Binding by a Podand Ionophore

  摘要：

  A simple, dye(R)-labeled and conformationally restricted ionophore 2 was prepared and screened for peptide binding using solid-supported combinatorial libraries of 24 389 protected and unprotected tripeptides. The ionophore was found generally to bind unhindered cationic peptides having arginines or N-terminal glycines. The podand was particularly selective in the case of unprotected tripeptides and was able to selectively bind a single tripeptide (L-Arg-L-Phe-D-AsP) from the unprotected similar to 24000-member tripeptide library. These results indicate that relatively simple organic molecules can make highly sequence-selective receptors for tripeptides. Structural features of such receptors are discussed.

  DOI：

  10.1021/jo970256w
• 作为产物：
  描述：

  [(2R,3R,4S)-2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-methyl-tetrahydro-pyran-4-yl]-carbamic acid 9H-fluoren-9-ylmethyl ester 在 三氟乙酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 56.0h， 以83%的产率得到[(2R,3R,4S)-2-((R)-1,2-Dihydroxy-ethyl)-3-methyl-tetrahydro-pyran-4-yl]-carbamic acid 9H-fluoren-9-ylmethyl ester
  参考文献：
  名称：

  Simple Structural Requirements for Sequence-Selective Peptide Receptors? Tripeptide Binding by a Podand Ionophore

  摘要：

  A simple, dye(R)-labeled and conformationally restricted ionophore 2 was prepared and screened for peptide binding using solid-supported combinatorial libraries of 24 389 protected and unprotected tripeptides. The ionophore was found generally to bind unhindered cationic peptides having arginines or N-terminal glycines. The podand was particularly selective in the case of unprotected tripeptides and was able to selectively bind a single tripeptide (L-Arg-L-Phe-D-AsP) from the unprotected similar to 24000-member tripeptide library. These results indicate that relatively simple organic molecules can make highly sequence-selective receptors for tripeptides. Structural features of such receptors are discussed.

  DOI：

  10.1021/jo970256w

文献信息

• Simple Structural Requirements for Sequence-Selective Peptide Receptors? Tripeptide Binding by a Podand Ionophore
  作者：Matthew T. Burger、W. Clark Still

  DOI：10.1021/jo970256w

  日期：1997.7.1

  A simple, dye(R)-labeled and conformationally restricted ionophore 2 was prepared and screened for peptide binding using solid-supported combinatorial libraries of 24 389 protected and unprotected tripeptides. The ionophore was found generally to bind unhindered cationic peptides having arginines or N-terminal glycines. The podand was particularly selective in the case of unprotected tripeptides and was able to selectively bind a single tripeptide (L-Arg-L-Phe-D-AsP) from the unprotected similar to 24000-member tripeptide library. These results indicate that relatively simple organic molecules can make highly sequence-selective receptors for tripeptides. Structural features of such receptors are discussed.