methyl (3S)-3-[(3aR,5R,6S,6aR)-6-methoxy-2,2-dimethylperhydrofuro[2,3-d][1,3]dioxol-5-yl]-3-aminopropanoate | 758711-29-4

• 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: methyl (3S)-3-[(3aR,5R,6S,6aR)-6-methoxy-2,2-dimethylperhydrofuro[2,3-d][1,3]dioxol-5-yl]-3-aminopropanoate
• 英文别名: methyl (3S)-3-[(3aR,5R,6S,6aR)-6-methoxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-3-aminopropanoate
• CAS: 758711-29-4
• 化学式: C₁₂H₂₁NO₆
• 分子量: 275.302
• InChiKey: YRIVNLPKEMNSQB-WAWIWLGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  89.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (3S)-3-[(3aR,5R,6S,6aR)-6-methoxy-2,2-dimethylperhydrofuro[2,3-d][1,3]dioxol-5-yl]-3-aminopropanoate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以0.82 g的产率得到(3S)-3-[(3aR,5R,6S,6aR)-6-methoxy-2,2-dimethylperhydrofuro[2,3-d][1,3]dioxol-5-yl]-3-aminopropan-1-ol
  参考文献：
  名称：

  α/δ-杂合肽的合成和结构—在Foldamers中获得新型螺旋结构的途径

  摘要：

  折纸肽：通过利用由D-葡萄糖和D-木糖与呋喃糖侧合成的新δ-氨基酸侧链的刚性，从理论和实验上研究了由α/δ-混合肽组成的一类新型折叠剂链（见图）。

  DOI：

  10.1002/chem.200802078
• 作为产物：
  描述：

  methyl (3S)-3-[(tert-butoxy)carbonylamino]-3-[6-methoxy-2,2-dimethyl-(3aR,6S,6aR)-tetrahydrofuro-[2,3-d][1,3]dioxol-5-yl]propanoate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 methyl (3S)-3-[(3aR,5R,6S,6aR)-6-methoxy-2,2-dimethylperhydrofuro[2,3-d][1,3]dioxol-5-yl]-3-aminopropanoate
  参考文献：
  名称：

  Robust Mixed 10/12 Helices Promoted by “Alternating Chirality” in a New Family of C-Linked Carbo-β-peptides

  摘要：

  The C-linked carbo-beta-peptides, oligomers of a new class of C-linked carbo-beta3-amino acids, have been shown to generate mixed 12/10 and 10/12 helices. The design involves use of "alternating chirality" of the epimeric (at the amine center) monomers to control the stability of these helices. The observation of stable 12/10 helix in a tripeptide and 10/12 helix in a tetrapeptide is unprecedented.

  DOI：

  10.1021/ja035752i

文献信息

• Rapid and facile Lewis acid catalysed Boc protection of amines
  作者：G.V.M. Sharma、J. Janardhan Reddy、P. Sree Lakshmi、Palakodety Radha Krishna

  DOI：10.1016/j.tetlet.2004.07.072

  日期：2004.9

  Efficient Boc protection of amines was carried out using (Boc)2O in the presence of a catalytic amount of ZrCl4 (10 mol %) in acetonitrile at room temperature. The reaction times are very short and the yields are generally high.

  在室温下，在乙腈中催化量的ZrCl 4（10 mol％）存在下，使用（Boc）2 O对胺进行有效的Boc保护。反应时间非常短，并且产率通常很高。
• Preparation of Sugar β-Amino Acid Derivatives with Cyclic Structures by Ring-Closing Metathesis
  作者：Basker Sundararaju、Tailor Sridhar、Mathieu Achard、Gangavaram V. M. Sharma、Christian Bruneau

  DOI：10.1002/ejoc.201000923

  日期：2010.11

  Efficient syntheses of β-amino acid derivatives with cyclic structures were developed. The key steps involve aza-Michael addition and ruthenium-catalyzed allylation for the construction of new acyclic β-amino acid dienes incorporating a sugar fragment, and a ruthenium-catalyzed ring-closing metathesis for the construction of the seven- and nine-membered ring compounds.

  开发了具有环状结构的β-氨基酸衍生物的有效合成。关键步骤包括 aza-Michael 加成和钌催化烯丙基化，用于构建包含糖片段的新无环 β-氨基酸二烯，以及用于构建七元和九元环的钌催化闭环复分解化合物。
• The stereoselective synthesis of C-linked 4′-deoxy aza-disaccharides from C-linked carbo-β-amino acids
  作者：G.V.M. Sharma、Nagendar Pendem、K. Ravinder Reddy、Palakodety Radha Krishna、K. Narsimulu、A.C. Kunwar

  DOI：10.1016/j.tetlet.2004.10.014

  日期：2004.11

  The stereoselective synthesis of 4'-deoxy aza-disaccharides in a concise and practical approach is described from C-linked carbo-beta-amino acid esters and this protocol utilizes an intramolecular amide bond formation and cis-dihydroxylation for the construction of the new sugar ring. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis and Structure of α/δ-Hybrid Peptides-Access to Novel Helix Patterns in Foldamers
  作者：Gangavaram V. M. Sharma、Bommagani Shoban Babu、Kallaganti V. S. Ramakrishna、Pendem Nagendar、Ajit C. Kunwar、Peter Schramm、Carsten Baldauf、Hans-Jörg Hofmann

  DOI：10.1002/chem.200802078

  日期：2009.5.25

  Origami peptides: A novel class of foldamers consisting of α/δ‐hybrid peptides has been investigated theoretically and experimentally by exploiting the rigidity of the side chain of a new δ‐amino acid prepared from D‐glucose and D‐xylose with a furanose side chain (see figure).

  折纸肽：通过利用由D-葡萄糖和D-木糖与呋喃糖侧合成的新δ-氨基酸侧链的刚性，从理论和实验上研究了由α/δ-混合肽组成的一类新型折叠剂链（见图）。
• Robust Mixed 10/12 Helices Promoted by “Alternating Chirality” in a New Family of C-Linked Carbo-β-peptides
  作者：Gangavaram V. M. Sharma、K. Ravinder Reddy、Palakodety Radha Krishna、A. Ravi Sankar、K. Narsimulu、S. Kiran Kumar、P. Jayaprakash、B. Jagannadh、A. C. Kunwar

  DOI：10.1021/ja035752i

  日期：2003.11.1

  The C-linked carbo-beta-peptides, oligomers of a new class of C-linked carbo-beta3-amino acids, have been shown to generate mixed 12/10 and 10/12 helices. The design involves use of "alternating chirality" of the epimeric (at the amine center) monomers to control the stability of these helices. The observation of stable 12/10 helix in a tripeptide and 10/12 helix in a tetrapeptide is unprecedented.