202477-59-6

Basic information

• Product Name: (2S,4R)-1-BOC-4-METHANESULFONYLOXY-PROLINE
• Synonyms: (2S,4R)-1-BOC-4-METHANESULFONYLOXY-PROLINE;(2S,4R)-4-Methanesulfonyloxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester;(2S,4R)-4-[(Methylsulfonyl)oxy]-1,2-pyrrolidinedicarboxylic acid 1-(1,1-dimethylethyl) ester
• CAS NO: 202477-59-6
• Molecular Formula: C₁₁H₁₉NO₇S
• Molecular Weight: 309.34
• Mol File: 202477-59-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 103℃ (heptane )
• Boiling Point: 500.1°C at 760 mmHg
• Flash Point: 256.3°C
• Appearance: /
• Density: 1.38g/cm³
• Vapor Pressure: 2.32E-11mmHg at 25°C
• Refractive Index: 1.528
• Storage Temp.: 2-8°C
• PKA: 3.53±0.40(Predicted)
• CAS DataBase Reference: (2S,4R)-1-BOC-4-METHANESULFONYLOXY-PROLINE(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,4R)-1-BOC-4-METHANESULFONYLOXY-PROLINE(202477-59-6)
• EPA Substance Registry System: (2S,4R)-1-BOC-4-METHANESULFONYLOXY-PROLINE(202477-59-6)

Safety Data

• Hazardous Substances Data: 202477-59-6(Hazardous Substances Data)

Usage

General Description

(2S,4R)-1-BOC-4-METHANESULFONYLOXY-PROLINE is a chemical compound that belongs to the class of proline derivatives. It is a derivative of proline that has a BOC (tert-butoxycarbonyl) protecting group at the 1-position and a methanesulfonyloxy group at the 4-position. (2S,4R)-1-BOC-4-METHANESULFONYLOXY-PROLINE is often used in organic synthesis and peptide chemistry as a building block for the synthesis of various proline-containing compounds. It is known for its ability to selectively functionalize the proline moiety in a substrate and has been used in the development of proline-based catalysts and ligands. Additionally, (2S,4R)-1-BOC-4-METHANESULFONYLOXY-PROLINE has been investigated for its potential biological activities, including its anti-inflammatory and anti-cancer properties. Overall, this compound is important for both chemical and biological research due to its versatile reactivity and potential pharmacological activities.

InChI:InChI=1/C11H19NO7S/c1-11(2,3)18-10(15)12-6-7(19-20(4,16)17)5-8(12)9(13)14/h7-8H,5-6H2,1-4H3,(H,13,14)/t7-,8+/m1/s1

Upstream product

• 84520-67-2 (2S,4R)-4-(methylsulfonyloxy)pyrrolidine-1,2-dicarboxylic acid 1-tert-butylester-2-methylester 
• 13726-69-7 (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid 
• 124-63-0 methanesulfonyl chloride 

Downstream Products

• 1218934-85-0 (3R,4S,7R)-2-benzyl-7-methanesulfonyloxy-1-oxo-3-phenyl-2,5-diazaspiro[3.4]octane-5-carboxylic acid tert-butyl ester 
• 788801-45-6 [tert-butoxycarbonyl-(1-cyclohexylmethyl-2-{2-[(6-methylsulfanylcarbonimidoyl-pyridin-3-ylmethyl)-carbamoyl]-2,5-dihydro-pyrrol-1-yl}-2-oxo-ethyl)-amino]-acetic acid tert-butyl ester 
• 182291-44-7 [tert-butoxycarbonyl-(1-cyclohexylmethyl-2-oxo-2-{2-[(6-thiocarbamoyl-pyridin-3-ylmethyl)-carbamoyl]-2,5-dihydro-pyrrol-1-yl}-ethyl)-amino]-acetic acid tert-butyl ester 
• 182291-43-6 tert-butyl {(tert-butoxycarbonyl)[(1R)-2-[(2S)-2-({[(6-cyano-3-pyridinyl)methyl]amino}carbonyl)-2,5-dihydro-1H-pyrrol-1-yl]-1-(cyclohexylmethyl)-2-oxoethyl]amino}acetate 
• 300832-84-2 ciluprevir 
• 769167-58-0 (1S,2R)-1-{[(2S,4S)-4-(4-bromo-benzenesulfonyloxy)-1-((S)-2-cyclopentyloxycarbonylamino-oct-7-enoyl)pyrrolidine-2-carbonyl]-amino}-2-vinylcyclopropanecarboxylic acid methyl ester 
• 782479-05-4 (1S,4R,6S,7Z,14S,18S)-18-(4-bromo-benzenesulfonyloxy)-14-cyclopentyloxycarbonylamino-2,15-dioxo-3,16-diaza-tricyclo[14.3.0.0^4,6]nonadec-7-ene-4-carboxylic acid methyl ester 
• 87250-97-3 2’-methyl-2’-propanyl (1S,4S)-3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate 

Relevant articles and documents

Design and synthesis of galactose-conjugated fluorinated and non-fluorinated proline oligomers: Towards antifreeze molecules

Galactose-conjugated fluorinated and non-fluorinated proline oligomers that exhibit an α-helical structure with hydrophilic and lipophilic parts were designed as potential antifreeze molecules. These galactose-proline oligomers were synthesized and their physical properties were evaluated. Interestingly, the non-fluorinated galactose-proline oligomers showed in contrast to the fluorinated analogues weak antifreeze activity. The difference in antifreeze activity should be attributed to the fluorine gauche effect, which should induce a conformation in fluorinated prolines that is different from that of natural proline. The results obtained in this study thus suggest that the 3D conformation of the galactose-conjugated fluorinated and non-fluorinated proline oligomers is very important for their anti-freezing properties.

Orally active thrombin inhibitors. Part 2: Optimization of the P2-moiety

Synthesis and SAR of orally active thrombin inhibitors of the d-Phe-Pro-Arg type with focus on the P2-moiety are described. The unexpected increase in in vitro potency, oral bioavailability, and in vivo activity of inhibitors with dehydroproline as P2-isostere is discussed. Over a period of 24 h the antithrombin activity of the most active inhibitors with IC50s in the nanomolar range was determined in dogs demonstrating high thrombin inhibitory activity in plasma and an appropriate duration of action after oral administration.

Technical scale synthesis of a new and highly potent thrombin inhibitor

In this account, we describe the development of an efficient and convergent process for the peptidomimetic thrombin inhibitor 1 on production plant scale. Starting from nicotinonitrile (13), (2S,4R)-1-(tert-butoxycarbonyl)-4-hydroxy-2- pyrrolidinecarboxylic acid (5) and (2R)-2-amino-3-cyclohexylpropanoic acid (29) compound 1 was obtained in 16 chemical steps. New methods had been developed for the preparation of the key intermediate dehydroproline 22 and the transformation of nitriles into amidines. The thrombin inhibitor 1 was isolated by special techniques (nanofiltration and spray drying). Almost all salts of 1 are amorphous, however, a crystalline complex was obtained with 1,2-benzisothiazol-3(2H)-one 1,1-dioxide (Saccharin).