110905-24-3

Upstream product

• 184714-56-5 (R)-4-benzyl-3-(2-chloroacetyl)oxazolidin-2-one 
• 275378-96-6 (R)-N-Carbamyl-phenylalanine methyl ester 
• 275378-91-1 ((R)-1-Hydroxymethyl-2-phenyl-ethyl)-urea 
• 3530-82-3 5-benzyl-hydantoin 
• 40217-17-2 (R)-4-(phenylmethyl)-2-oxazolidinone 
• 54896-72-9 (R)-3-phenyl-2-ureido-propionic acid 
• 22118-09-8 2-bromoacetyl chloride 
• 598-21-0 2-Bromoacetyl bromide 

Downstream Products

• 201231-65-4 (R)-4-Benzyl-3-[2-(triphenyl-λ⁵-phosphanylidene)-acetyl]-oxazolidin-2-one 
• 204587-88-2 [2-((R)-4-benzyl-2-oxooxazolidin-3-yl)-2-oxoethyl]phosphonic acid diethyl ester 
• 950479-13-7 (4R,3'S,4'R,5'R)-4-benzyl-[5'-[(4-methoxybenzyl)oxy]-3'-hydroxy-4'-methylheptnaoyl]-2-oxazolidinone 
• 110905-26-5 (4R)-3-((2'S,3'S)-2'-azido-3'-hydroxy-4'-methyl-4'-pentenoyl)-4-(phenylmethyl)-2-oxazolidinone 
• 136620-81-0 (4R)-3-((2'S,3'S)-2'-azido-3'-hydroxy-3'-phenylpropanoyl)-4-(phenylmethyl)-2-oxazolidinone 
• 110905-25-4 (4R)-3-((2'R,3'S)-2'-bromo-3'-hydroxy-4'-methyl-4'-pentenoyl)-4-(phenylmethyl)-2-oxazolidinone 
• 1174528-02-9 C₂₀H₂₁NO₅ 
• 137789-54-9 [2-(4-benzyl-2-oxo-oxazolidin-3-yl)-2-oxo-ethyl]-phosphonic acid diethyl ester 
• 113122-43-3 Methyl-carbamic acid (E)-(1S,2R)-1-[(R)-2-((R)-4-benzyl-2-oxo-oxazolidin-3-yl)-1-bromo-2-oxo-ethyl]-2-methyl-hex-4-enyl ester 

Relevant academic research and scientific papers

Towards the total synthesis of marineosin A: Construction of the macrocyclic pyrrole and an advanced, functionalized spiroaminal model

Herein, we describe the enantioselective construction of the 12-membered macrocyclic pyrrole core of marineosin A in 5.1 % overall yield from (S)-propylene oxide. The route features a key Stetter reaction to install a 1,4-diketone, which is subjected to Paal-Knorr pyrrole synthesis and ring-closing metathesis to afford the macrocycle. A divergence point in the synthetic scheme also enabled access to a highly functionalized spiroaminal model system through an acid-mediated hydroxy oxo amide cyclization strategy. Copyright

Identification of a nonbasic, nitrile-containing cathepsin K inhibitor (MK-1256) that is efficacious in a monkey model of osteoporosis

Herein, we report on the identification of nonbasic, potent, and highly selective, nitrile-containing cathepsin K (Cat K) inhibitors that are built on our previously identified cyclohexanecarboxamide core structure. Subsequent to our initial investigation

A short approach to the bicyclo[4.3.0]nonane fragment of stawamycin

The bicyclo[4.3.0]nonane (C11-C21) fragment of stawamycin has been prepared by a sequence involving 11 steps (10% overall yield) from methyl (R)-(-)-3-hydroxy-2-methylpropionate. Key steps are a Pd-catalysed Stille coupling reaction

Fluoro- and trifluoroalkyl-containing heterocyclic sulfonamide inhibitors of beta amyloid production and derivatives thereof

Compounds of Formula (I), are provided where T is CHO, CON, or C(OH)R1R2; R1 and R2 are hydrogen, optionally substituted lower alkyl, CF3, optionally substituted alkenyl, or optionally substituted alkynyl; R3 is hydrogen or optionally substituted lower alkyl; R4 is (CF3)nalkyl, (CF3)n(substitutedalkyl), (CF3)nalkylphenyl, (CF3)nalkyl(substitutedphenyl), or (F)ncycloalkyl; n=1-3; R5 is hydrogen, halogen, CF3, diene fused to Y when Y═C, or substituted diene fused to Y when Y═C; W, Y and Z are C, CR6 or N where at least one of W, Y or Z are C; R6 is hydrogen, halogen, or optionally substituted lower alkyl; X is O, S, SO2, or NR7; R7 is hydrogen, optionally substituted lower alkyl, optionally substituted benzyl, or optionally substituted phenyl; and R8 is lower alkyl, CF3, or optionally substituted phenyl. Methods of preparing and using these compounds for inhibiting beta amyloid production and for treatment of Alzheimer's Disease and Down's syndrome are also described.

Total synthesis of a stereoisomer of bistramide C and assignment of configuration of the natural product

After the isolation of the bioactive polyether bistramide C from the marine ascidian Lissoclinum bistratum in 1988, NMR spectroscopic investigations over the next 12 years reduced the total number of possible stereoisomers of this compound from 1024 to 32. Based on the preparation of segments of the natural product as well as the total synthesis of a randomly selected stereoisomer of bistramide C, the stereochemical puzzle could be further simplified to eight possible stereoisomers. A convergent three-segment coupling strategy, the use of a common, D-glucose-derived intermediate for the preparation of pyran rings in two segments, a stereoselective photo-spiroketalization, and the use of azides to minimize protective group manipulations before segment couplings are highlights of the synthetic approach. The total synthesis also provided the key segments for a chiroptical analysis according to van't Hoff's principle of optical superposition, which was crucial for the assignment of a sole relative and absolute configuration of the natural product. Bistramide C represents therefore the first member of this class of structurally unusual marine polyethers whose configuration is known as a result of the combined use of synthetic and chiroptical tools.

Synthesis of triketide δ-lactones

An efficient synthetic route was developed to prepare substituted δ-lactones 1 and 2 in enantiopure forms which are potentially useful for biosynthetic studies with genetically engineered modular polyketide synthase (PKS). The key step to prepare the targ

N-carbamylamino alcohols as the precursors of oxazolidinones via nitrosation-deamination reaction

Oxazolidinones were effectively prepared from N-carbamylamino alcohols by treatment with nitrous acid, via N-nitroso compound as the intermediate. A new route to (R)-4-benzyloxazolidinone was developed starting from DL- phenylalanine, utilizing D-hydantoinase-catalyzed enantioselective hydrolysis of 5-benzylhydantoin under the dynamic kinetic resolution conditions, and the subsequent reduction to the precursor for the above-mentioned cyclization reaction, by taking advantage of the intermediates bearing an N-carbamylamino functionality.