(2R,5R)-5-((S)-1-tert-Butoxycarbonylamino-ethyl)-tetrahydro-furan-2-carboxylic acid | 873217-99-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (2R,5R)-5-((S)-1-tert-Butoxycarbonylamino-ethyl)-tetrahydro-furan-2-carboxylic acid
• 英文别名: (2R,5R)-5-[(1S)-1-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]oxolane-2-carboxylic acid
• CAS: 873217-99-3
• 化学式: C₁₂H₂₁NO₅
• 分子量: 259.302
• InChiKey: OESPOHHPFMGZPY-DJLDLDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,5R)-5-((S)-1-tert-Butoxycarbonylamino-ethyl)-tetrahydro-furan-2-carboxylic acid 、 重氮甲烷 以 乙醚 为溶剂， 生成 (2R,5R)-5-((S)-1-tert-Butoxycarbonylamino-ethyl)-tetrahydro-furan-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of C6-substituted 3,4-dideoxy furanoid sugar amino acids

  摘要：

  A variety of chiral 3,4-dideoxy furanoid sugar amino acids have been synthesized, which were substituted at C6 with different alkyl groups, such as methyl, benzyl, isopropyl and hydroxymethyl synthesized from their corresponding N,N-dibenzy-laminoaldehydes. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.058
• 作为产物：
  描述：

  (3R,4S)-4-Dibenzylamino-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pent-1-yn-3-ol 在 palladium dihydroxide 吡啶 、 sodium chlorite 、 disodium hydrogenphosphate 、 2-甲基-2-丁烯 、 camphor-10-sulfonic acid 、 氢气 、 三氧化硫吡啶 、 potassium carbonate 、 二甲基亚砜 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 叔丁醇 为溶剂， 生成 (2R,5R)-5-((S)-1-tert-Butoxycarbonylamino-ethyl)-tetrahydro-furan-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of C6-substituted 3,4-dideoxy furanoid sugar amino acids

  摘要：

  A variety of chiral 3,4-dideoxy furanoid sugar amino acids have been synthesized, which were substituted at C6 with different alkyl groups, such as methyl, benzyl, isopropyl and hydroxymethyl synthesized from their corresponding N,N-dibenzy-laminoaldehydes. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.058

文献信息

• Novel C6-substituted furanoid sugar amino acids and improved process for preparing the same
  申请人：Chakraborty Kanti Tushar

  公开号：US20060014939A1

  公开（公告）日：2006-01-19

  The present invention relates to furanoid sugar amino acids and their salts which carrying an additional chiral center at C6-position with substituents and resembling the side-chains of natural amino acids. More particularly, 6-substituted-6-deoxy-6-amino-2,5-anhydroaldonic acids and their 3,4-dideoxy congeners, in enantiomerically pure forms, which constitute an important class of conformationally constrained peptide building blocks that can be used as dipeptide isosteres in peptidomimetic studies. R 1 =H, Boc, Cbz, Fmoc, acetyl or salts such as HCl, TFA R 2 =CH 3 —, (CH 3 ) 2 CH—, (CH 3 ) 2 CHCH 2 —, CH 3 CH 2 CH(CH 3 )—, alkyl groups, OR 3 )CH 2 —, CH 3 (OR 3 )CH—, (R 3 S)CH 2 —, CH 3 SCH 2 CH 2 —, (RHN)CH 2 CH 2 CH 2 CH 2 —, (CONH 2 )CH 2 —, (CONH 2 )CH 2 CH 2 —, (CO 2 R 5 )CH 2 —, (CO 2 R 5 )CH 2 CH 2 —, Ph-, Ar-, PhCH 2 —, ArCH 2 —, Phenylalkyl-, arylalkyl-, (indolyl)CH 2 —, (imidazolyl)CH 2 —, and all other amino acid side-chains R 3 =H, tert-butyl, alkyl, benzyl, arylCH 2 , CO(alkyl), CO(arylalkyl), SO 3 H, PO 3 H 2 , silyl, R 4 =—O-alkyl, —O-arylalkyl, -amine, -alkylamine, -arylalkylamine, and others R 5 =H, tert-butyl, alkyl, benzyl, arylCH 2 , R 1 -R 2 =—(CH 2 ) n — (n=2,3,4)

  该发明涉及呋喃糖氨基酸及其盐，其在C6位置携带具有取代基的额外手性中心，并类似于天然氨基酸的侧链。更具体地说，6-取代-6-去氧-6-氨基-2,5-缩水醛酸及其3,4-二去氧同分异构体，以对映异构纯形式存在，构成一类重要的构象受限的肽段构建块，可用作肽类模拟研究中的二肽同分异构体。R1=H，Boc，Cbz，Fmoc，乙酰基或盐，如HCl，TFA；R2=CH3—，（CH3）2CH—，（CH3）2CHCH2—，CH3CH2CH（CH3）—，烷基，OR3）CH2—，CH3（OR3）CH—，（R3S）CH2—，CH3SCH2CH2—，（RHN）CH2CH2CH2CH2—，（CONH2）CH2—，（CONH2）CH2CH2—，（CO2R5）CH2—，（CO2R5）CH2CH2—，Ph-，Ar-，PhCH2—，ArCH2—，苯基烷基-，芳基烷基-，（吲哚基）CH2—，（咪唑基）CH2—，以及所有其他氨基酸侧链；R3=H，叔丁基，烷基，苄基，芳基CH2，CO（烷基），CO（芳基烷基），SO3H，PO3H2，硅基；R4=—O-烷基，—O-芳基烷基，-胺，-烷基胺，-芳基烷基胺，等；R5=H，叔丁基，烷基，苄基，芳基CH2；R1-R2=—（CH2）n—（n=2,3,4）。
• Synthesis of C6-substituted 3,4-dideoxy furanoid sugar amino acids
  作者：Tushar Kanti Chakraborty、Gangarajula Sudhakar

  DOI：10.1016/j.tetasy.2004.11.058

  日期：2005.1

  A variety of chiral 3,4-dideoxy furanoid sugar amino acids have been synthesized, which were substituted at C6 with different alkyl groups, such as methyl, benzyl, isopropyl and hydroxymethyl synthesized from their corresponding N,N-dibenzy-laminoaldehydes. (C) 2004 Elsevier Ltd. All rights reserved.