A novel 2H-azirin-3-amine as a synthon for a sulfur containing dipeptide segment

نویسندگان

  • Svetlana A. Stoykova
  • Anthony Linden
چکیده

Starting with tetrahydro-2H-thiopyran-4-carboxylic acid and methyl prolinate, the novel 2Hazirin-3-amine (S)-N-(1-aza-6-thiaspiro[2.5]oct-1-en-2-yl)proline methyl ester was synthesized. In reactions with benzoic acid, thiobenzoic acid and Boc-valine, respectively, its usefulness as a synthon for the dipeptide (S)-N-[(4-aminotetrahydro-2H-thiopyran-4-yl)carbonyl]proline in peptide synthesis was demonstrated. DOI: https://doi.org/10.1080/17415993.2013.774401 Posted at the Zurich Open Repository and Archive, University of Zurich ZORA URL: https://doi.org/10.5167/uzh-78018 Accepted Version Originally published at: Stoykova, Svetlana A; Linden, Anthony; Heimgartner, Heinz (2014). A novel 2H-azirin-3-amine as a synthon for a sulfur containing dipeptide segment. Journal of Sulfur Chemistry, 35(1):14-23. DOI: https://doi.org/10.1080/17415993.2013.774401

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Highly chemo-, enantio-, and diastereoselective [4 + 2] cycloaddition of 5H-thiazol-4-ones with N-itaconimides

A dipeptide-based urea-amide tertiary amine (DP-UAA) was shown to be an effective Brønsted base catalyst for the first asymmetric annulation reaction between 5H-thiazol-4-ones and N-itaconimides. High levels of enantioselectivity (up to 99% ee) and diastereoselectivity (>19:1 dr) were obtained for a series of spirocyclic 1,4-sulfur-bridged piperidinone-based succinimides.

متن کامل

DABCO-catalyzed unusual [4 + 2] cycloaddition reaction: non-substituted allenoate acts as a four-carbon synthon and facile synthesis of spirooxindoles.

A DABCO-catalyzed domino reaction between methyleneoxindoles and allenoates which enables the direct synthesis of spirooxindoles is reported. This is the first example of a non-substituted allenoate to act as a four-carbon synthon in a tertiary amine-catalyzed reaction.

متن کامل

Experimental and theoretical characterization of the valence isomerization of Bi-2H-azirin-2-yls to diazabenzenes.

3,4-diazidocyclobutenes 16 were prepared from the corresponding dihalides. Some of these diazides, such as parent compound 16 d and phenyl-substituted derivatives 16 c,f, underwent spontaneous stereoselective electrocyclic ring opening below room temperature, whereas the tetraalkyl derivatives of 16 had to be heated to force the same reaction. In most cases, the resulting 1,4-diazidobuta-1,3-di...

متن کامل

Electrocatalytic multicomponent assembling of aldehydes, dimedone and 1-naphthylamine for synthesis of novel tetrahydrobenzo[c]acridin-8(7H)-one derivatives

An efficient and convenient synthesis of novel tetrahydrobenzo[c]acridin-8(7H)-one derivatives is described using the electrogenerated anion of acetonitriles as the base in the presence of tetrabutylammonium fluoride as an effective supporting electrolyte in a one-pot, three-component condensation of aromatic aldehyde, dimedone and 1-naphthyl amine. The reaction is carried out in an undivided c...

متن کامل

Solubility of Hydrogen Sulfid and Sulfur Dioxide in Triethylen Glycol, Tetra Ethylene Clycol and Diethanol (TECHNICAL NOTE). AMINE SOLUTION

Natural gas sweetening is an important process which is used for treatment of sour gases. The measurement of solubility is also considered in most sweetening processes such as that of Townsend process. Therefore, experimental measurements would be helpful to determine the equilibrium data under actual equilibrium conditions for the gas treatment plants. In this research solubility of hydrogen s...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:

دوره   شماره 

صفحات  -

تاریخ انتشار 2017