tert-butyl N-(1S)-1-[(3aR,5R,6S,6aR)-6-methoxy-2,2-dimethylperhydrofuro[2,3-d][1,3]dioxol-5-yl]-3-hydroxypropylcarbamate | 809281-09-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl N-(1S)-1-[(3aR,5R,6S,6aR)-6-methoxy-2,2-dimethylperhydrofuro[2,3-d][1,3]dioxol-5-yl]-3-hydroxypropylcarbamate
• 英文别名: tert-butyl N-[(1S)-1-[(3aR,5R,6S,6aR)-6-methoxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-3-hydroxypropyl]carbamate
• CAS: 809281-09-2
• 化学式: C₁₆H₂₉NO₇
• 分子量: 347.409
• InChiKey: XYKBAYIHUIEMIJ-OBPIAQAESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  95.5
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl N-(1S)-1-[(3aR,5R,6S,6aR)-6-methoxy-2,2-dimethylperhydrofuro[2,3-d][1,3]dioxol-5-yl]-3-hydroxypropylcarbamate 在 2-碘酰基苯甲酸 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 12.0h， 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 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 27.0h， 生成 tert-butyl N-(1S)-1-[(3aR,5R,6S,6aR)-6-methoxy-2,2-dimethylperhydrofuro[2,3-d][1,3]dioxol-5-yl]-3-hydroxypropylcarbamate
  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.