84062-29-3

Upstream product

• 64-17-5 ethanol 
• 1666-13-3 diphenyl diselenide 
• 117811-78-6 methyl (2S,4R)-1-benzyloxycarbonyl-4-methanesulfonyloxypyrrolidine-2-carboxylate 
• 57653-38-0 N-<(phenylmethoxy)carbonyl>-4(R)-<<(4-methylphenyl)sulfonyl>oxy>-(S)-proline methyl ester 
• 103667-57-8 (2S,4R)-ethyl N¹-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylate 
• 33996-30-4 trans-4-hydroxy-L-proline ethyl ester hydrochloride 
• 501-53-1 benzyl chloroformate 
• 13504-85-3 (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid 
• 51-35-4 4R-4-hydroxyproline 
• 64187-48-0 methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate 
• 1499-56-5 (R)-4-hydroxy-L-proline ethyl ester 

Downstream Products

• 191851-81-7 1-benzyl 2-ethyl(2S)-2,5-dihydro-1H-pyrrole-1,2-dicarboxylate 
• 161708-52-7 C₆₂H₈₉N₇O₁₅ 
• 161708-51-6 (S)-2-{Methyl-[(R)-3-methyl-1-(2-trimethylsilanyl-ethoxycarbonyl)-butyl]-carbamoyl}-2,5-dihydro-pyrrole-1-carboxylic acid benzyl ester 
• 161708-41-4 N-Cbz-3,4-didehydro-L-prolyl-N-methyl-D-leucine 
• 161813-74-7 (S)-2,5-dihydro-pyrrole-1,2-dicarboxylic acid 1-benzyl ester 
• 120286-05-7 Cyclo<(N-L-prolyl-N-methyl-D-leucyl)-O-<oxy>-3-oxo-2,5-dimethylhexanoyl>-L-leucyl>-L-prolyl-N,O-dimethyl-L-tyrosyl>-L-threonyl> 

Relevant academic research and scientific papers

The preparation of (S)-3,4-dehydroproline from (2S,4R)-4-hydroxyproline

(2S,4R)-N-benzyloxycarbonyl-4-tosyloxyproline methyl ester, readily prepared from commercially available (2S,4R)-N-benzyloxycarbonyl-4-hydroxyproline, was converted to (S)-3,4-dehydroproline of high enantiomeric purity by a process which involved a highly regioselective phenylselenoxide elimination to introduce the olefinic function.

SUBSTITUTED HETEROCYCLIC SULFONAMIDE COMPOUNDS USEFUL AS TRPA1 MODULATORS

The invention is concerned with the compounds of formula I or II: and salts thereof. In addition, the present invention relates to methods of manufacturing and methods of using the compounds of formula I or II as well as pharmaceutical compositions containing such compounds. The compounds may be useful in treating diseases and conditions mediated by TRPA1, such as pain.

Synthesis of new didemnin B analogs for investigations of structure/biological activity relationships

Modifications were introduced in the side chain of didemnin B to afford several analogs (1f-1j) for biological testing in order to identify the features responsible for the bioactivity of the natural products (1a-1c). To achieve our goal, two changes were made in the proline ring of the b-turn side chain. Initially, a hydroxyl group was incorporated at the C-4 position of the ring to increase the polar nature of the molecule. Secondly, unsaturation was introduced at C-3 and C-4 to increase the rigidity of the ring and to provide a site for tritiation to follow the drug pathway in biological systems. Improvements were also introduced in the macrocycle construction to produce gram quantities of this unit (1d) for the preparation of the planned analogs. The linear precursor to the macrocycle was oxidized more effectively with 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one (Dess-Martin periodinane reagent), and cyclization yields were increased substantially by using a new coupling reagent, pentafluorophenyl diphenylphosphinate (FDPP). (1H-1,2,3-benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP) and pentafluorophenyl trifluoroacetate were also used to improve other coupling reactions.