(3S)-3-[(3aR,5R,6S,6aR)-6-methoxy-2,2-dimethylperhydrofuro[2,3-d][1,3]dioxol-5-yl]-3-aminopropan-1-ol | 809281-08-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S)-3-[(3aR,5R,6S,6aR)-6-methoxy-2,2-dimethylperhydrofuro[2,3-d][1,3]dioxol-5-yl]-3-aminopropan-1-ol
• 英文别名: (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-aminopropan-1-ol
• CAS: 809281-08-1
• 化学式: C₁₁H₂₁NO₅
• 分子量: 247.291
• InChiKey: YRGHRCFOTUGBAI-SQXHDICFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  83.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3S)-3-[(3aR,5R,6S,6aR)-6-methoxy-2,2-dimethylperhydrofuro[2,3-d][1,3]dioxol-5-yl]-3-aminopropan-1-ol 在 三乙胺 、 三氟乙酸 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 24.0h， 生成 (E)-(S)-5-tert-Butoxycarbonylamino-5-((3aR,5R,6S,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-pent-2-enoic acid ethyl ester
  参考文献：
  名称：

  The stereoselective synthesis of C-linked 4′-deoxy aza-disaccharides from C-linked carbo-β-amino acids

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2004.10.014
• 作为产物：
  描述：

  methyl (3S)-3-benzylamino-3-[6-methoxy-2,2-dimethyl-(3aR,5R,6S,6aR)-perhydrofuro[2,3-d][1,3]dioxol-5-yl]propanoate 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 24.0h， 生成 (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：

  The stereoselective synthesis of C-linked 4′-deoxy aza-disaccharides from C-linked carbo-β-amino acids

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2004.10.014

文献信息

• 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）。
• 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.