167645-47-8

Upstream product

• 16310-55-7 2-((benzyloxy)methyl)-2,3-dihydrofuran 
• 167645-50-3 5-benzyloxy-4-oxo-pentanoic acid methyl ester 
• 3587-60-8 Benzyloxymethyl chloride 
• 66274-27-9 5-hydroxy-4-oxopentanoic acid methyl ester 
• 53856-93-2 methyl 5-bromo-4-oxopentanoate 
• 107757-75-5 2-benzyloxymethyl-4,5-dihydrofuran 
• 167645-51-4 5-Benzyloxymethyl-5-hydroxy-5H-furan-2-one 

Downstream Products

• 176298-36-5 (3S,7aS)-7a-Benzyloxymethyl-3-phenyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one 
• 176095-96-8 (3S,6S,7R,7aR)-7a-Benzyloxymethyl-6,7-dihydroxy-3-phenyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one 
• 176095-95-7 (3aR,3bR,6S,7aS)-3b-Benzyloxymethyl-2,2-dimethyl-6-phenyl-tetrahydro-1,3,4-trioxa-6a-aza-cyclopenta[a]pentalen-7-one 
• 239136-90-4 (S)-2-((3aS,4R,6aR)-4-Benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-5-yl)-2-phenyl-ethanol 
• 176298-37-6 (3S,7aS)-7a-Benzyloxymethyl-3-phenyl-2,3-dihydro-7aH-pyrrolo[2,1-b]oxazol-5-one 
• 800367-25-3 (4S,8aR)-8a-benzyloxymethyl-4-phenyltetrahydro-pyrrolo[2,1c][1,4]oxazine-1,6-dione 

Relevant academic research and scientific papers

Palladium(II)-Catalyzed C(sp 3)-H Activation of N,O-Ketals towards a Method for the β-Functionalization of Ketones

A method for the formal β-functionalization of aliphatic ketones via a palladium-catalyzed sp 3 C-H activation pathway is reported. An N,O-ketal directs an aliphatic C-H carbonylation to form γ-lactams which upon hydrolysis generate γ-keto carb

Asymmetric synthesis of 2-alkyl-substituted 2-hydroxyglutaric acid γ-lactones

3-Alkyl-1,2-cyclopentanediones 1 are transformed into 2-alkyl-2-hydroxyglutaric acid γ-lactones 3 in up to 83% isolated yields and up to 96% ee, affording a simple access to many bioactive compounds, including diacylglycerol lactones (DAG-lactones).

Asymmetric Strecker reaction of γ-keto acids. Facile entry to α-substituted and α,γ-disubstituted glutamic acids

The Strecker reaction of γ-keto acid derived sodium salts with (S)-phenylglycinol followed by treatment of the resultant α-amino nitriles with methanolic HCl and heating at 200°C give bicyclic lactones 11 and 12. Hydrolysis and subsequent debenzylation of

Asymmetric routes to azasugars from chiral bicyclic lactams. Synthesis of 1,4-dideoxy-1,4-imino-d-lyxitol; L-Deoxymannojirimycin; rhammo-1- Deoxynojirimycin and 1-deoxy-6-epicastanospermine

Summary: By employing the appropriate chiral bicyclic lactams, the asymmetric total synthesis of four enantiopure azasugars mentioned in the title were successfully achieved. A series of diastereoselective oxidations (OsO4/NMO) followed by diastereoselective reductions (BH3, 9-BBN) gave good yields of the trisubstituted (16) and tetrasubstituted (2,3,4) pyrrolidine and piperidines respectively.

Syntheses of γ-oxo acids or γ-oxo esters by photooxygenation of furanic compounds and reduction under ultrasound: Application to the synthesis of 5-aminolevulinic acid hydrochloride

The photooxygenation of 5-hydroxymethyl-2-furfural (1a) or derivatives 1b-g yields 4-hydroxy-Δ2-butenolides 2 which are the percursors of butenolides 3 or α,β-unsaturated γ-oxo esters 5. The selective reduction of olides 2 or oxo esters 5 with zinc in acetic acid under sonication leads to γ-oxo acids 4 or γ-oxo esters 6. The photooxygenation of amino derivative 1d, followed by selective reduction of corresponding lactone 2d, gives 5-aminolevulinic acid hydrochloride (7) (ALA) after hydrolysis.