222307-13-3

Upstream product

• 13154-24-0 triisopropylsilyl chloride 
• 17342-08-4 (S)-Pyroglutaminol 

Downstream Products

• 222307-20-2 (S)-(+)-N-tert-butyloxycarbonyl-5-(triisopropylsilyloxymethyl)-3-phenylselenyl-pyrrolidin-2-one 
• 890139-84-1 2-((R)-1-Azidomethyl-2-phenyl-ethylcarbamoyl)-5-{(S)-3-[3-((R)-1-benzyl-prop-2-ynyl)-ureido]-4-triisopropylsilanyloxy-butyl}-furan-3,4-dicarboxylic acid dimethyl ester 
• 890139-80-7 2-((R)-1-Azidomethyl-2-phenyl-ethylcarbamoyl)-5-{(S)-3-[3-((S)-1-benzyl-prop-2-ynyl)-ureido]-4-triisopropylsilanyloxy-butyl}-furan-3,4-dicarboxylic acid dimethyl ester 
• 890139-82-9 2-((S)-1-Azidomethyl-2-phenyl-ethylcarbamoyl)-5-{(S)-3-[3-((R)-1-benzyl-prop-2-ynyl)-ureido]-4-triisopropylsilanyloxy-butyl}-furan-3,4-dicarboxylic acid dimethyl ester 
• 890139-78-3 2-((S)-1-Azidomethyl-2-phenyl-ethylcarbamoyl)-5-{(S)-3-[3-((S)-1-benzyl-prop-2-ynyl)-ureido]-4-triisopropylsilanyloxy-butyl}-furan-3,4-dicarboxylic acid dimethyl ester 

Relevant academic research and scientific papers

N-Heterocyclic carbene triazolium salts containing brominated aromatic motifs: Features and synthetic protocol

In this work, we provide a brief overview of the role of N-aryl substituents on triazolium N-heterocyclic carbene (NHC) catalysis. This synopsis provides context for the disclosed synthetic protocol for new chiral N-heterocyclic carbene (NHC) triazolium salts with brominated aromatic motifs. Incorporating brominated aryl rings into NHC structures is challenging, probably due to the substantial steric and electronic influence these substituents exert throughout the synthetic protocol. However, these exact characteristics make it an interesting N-aryl substituent, because the electronic and steric diversity it offers could find broad use in organometallic- A nd organo-catalysis. Following the synthetic reaction by NMR guided the extensive modification of a known protocol to enable the preparation of these challenging NHC pre-catalysts.

Practical Synthesis of Chiral N-Heterocyclic Carbene Triazolium Salts Containing a Hydroxy Functional Handle

A library of functionalized chiral pyrrolidine-based N-heterocyclic carbene triazolium salts containing a hydroxy handle is prepared from readily accessible chiral (S)-pyroglutamic acid in eight steps. This improved synthetic protocol affords increased yields for known structures and 18 new NHCs are prepared by this method. The presence of a hydroxy handle offers potential for further functionalization and for non-covalent control over catalytic reactions in which the NHCs can serve as organocatalysts or ligands for organometallic catalysis.

CARBONITRILE DERIVATIVES AS SELECTIVE ANDROGEN RECEPTOR MODULATORS

The present invention relates to a compound of Formula 1, 2 or 3: I II III wherein A is N or -CR0--, where R0 is hydrogen, C1-C6 linear or branched chain alkyl, etc., Z is -CRe --, or, -N--, where Re is hydrogen, C1 -C6 linear or branched chain alkyl, etc.; R1 is hydrogen, C1 -C6 linear or branched chain alkyl, etc.; R2 are independently hydrogen or C1-C6 linear or branched chain alkyl; R3 and R4 are independently hydrogen, C1C6 linear or branched chain alkyl, etc.;. R5 and R6 are independently hydrogen or C1-C6 linear or branched chain alkyl, etc.; R8 is hydrogen, C1 -C6 linear or branched chain alkyl, etc.; R9 and R10 are independently hydrogen or C1- C6 linear or branched chain alkyl, etc.; Q is --CO--, --(CH2)q--, --(CHRs)q--, or -(CRsRt)q- -, where Rs and Rt are independently C1-C6 linear or branched chain alkyl, aryl, alkylaryl, heteroaryl or alkylheteroaryl; where q is 0, 1, 2, or 3; and, where n is 0, 1, 2, 3, 4 or 5; or, a pharmaceutically acceptable salt thereof, for the treatment of certain diseases, particularly those affected or mediated by the androgen receptor; to compbinations comprising such compounds with a second pharmaceutically active ingredient; to compositions containing such combinations; and to such combinations for the treatment of various diseases, particularly, those affected or mediated by the androgen receptor.

HCV PROTEASE INHIBITORS

Novel compounds that are potent inhibitors of hepatitis C virus protease are provided. Pharmaceutical compositions containing one or more of these inhibitors, methods of preparing the inhibitors and methods of using the inhibitors to treat hepatitis C and related disorders also are provided.

Asymmetric intramolecular crossed-benzoin reactions by N-heterocyclic carbene catalysis

(Chemical Equation Presented) Getting cross: Excellent asymmetric inductions and very good yields are achieved in the generation of a quaternary stereocenter in α-hydroxy-substituted tetralones by using chiral N-heterocyclic carbene catalysts in an enantioselective intramolecular crossed-benzoin reaction. The synthesis of the corresponding α-hydroxyindanones with good ee values is also possible by this route.

A unified synthetic strategy toward oroidin-derived alkaloids premised on a biosynthetic proposal

Details of the evolution of a synthetic strategy toward the spirocyclic chlorocyclopentane core of oroidin-derived alkaloids, including the axinellamines and potentially adaptable to palau'amine, are described. A proposed refinement of the Kinnel-Scheuer biosynthetic proposal for palau'amine is posited. Studies undertaken to improve the regioselectivity and efficiency of a key Diels-Alder reaction utilizing a novel protecting group strategy, microwave chemistry, and other strategies are described. Further insights regarding the suitability of different protecting groups during the epoxidation/chlorination/ring contraction sequence are disclosed. Several interesting by-products from this reaction sequence are reported. These studies have led to a unified synthetic strategy to the axinellamines and palau'amine.

Photoinduced addition of methanol to 5(S)-5-triisopropylsiloxymethyl-N- boc-dihydropyrrole-2(5H)-one: A new route to 4(S), 5(S)-disubstituted pyrrolidin-2-ones

We describe the photoinduced addition of methanol to 5(S)-5- triisopropylsiloxymethyl-N-boc-dihydropyrrole-2(5H)-one to produce 5(S)-5- triisopropylsiloxymethyl-4(S)-hydroxymethyl-pyrrolidine-2-one, and conversion of this into a variety of 4(S), 5(S)-pyrrolidine-2-ones. Photo-induced addition of methanol to 5(R)-N-boc-5-amino-dihydropyran-2(5H)-one yielded the unexpected product 4(S)-1'-[2'-hydroxy, 1'-(R)-N-boc-amino]ethyl- tetrahydrofuran-2-one via rearrangement of the initial photoadduct.