1576-92-7

Upstream product

• 532-32-1 sodium benzoate 
• 821-06-7 (E)-1,4-dibromobutene 
• 132294-16-7 (2S-trans)-2,3-bis[(benzoyloxy)methyl]cyclobutanone 
• 87-42-3 6-chloropurine 
• 362-43-6 2',3'-O-isopropylideneuridine 
• 20031-21-4 1,2-O-isopropylidene-α-D-xylose 
• 138736-93-3 C₂₂H₂₄O₆ 
• 821-11-4 trans-butene-1,4-diol 
• 769-78-8 vinyl benzoate 
• 75-65-0 tert-butyl alcohol 
• 67-56-1 methanol 
• 123-56-8 Succinimide 
• 98-88-4 benzoyl chloride 
• 582-25-2 Potassium benzoate 

Downstream Products

• 7433-56-9 (E)-5-decene 
• 19224-27-2 1,4-bis(benzoyloxy)butane 

Relevant academic research and scientific papers

A novel photochemical synthesis of dideoxyfuranosyl disaccharides

A photochemical glycosylation is described using the chiral cyclobutanone 1. Irradiation of ketone 1 in the presence of monosaccharides 2 and 3 gives photoadducts derived from OH insertion of the transient carbene. The carbene inserts into the N-H group in the case of nucleoside 4.

Synthesis and HIV inhibition activity of 2',3'-dideoxy-3'-C- hydroxymethyl nucleosides

A series if 2',3'-dideoxy-3'-C-hydroxymethyl purine nucleosides were prepared based on the photochemical ring expansion of a chiral cyclobutanone precursor, (2S)-trans-2,3-bis[(benzoyl-oxy)methyl]cyclobutanone, in the presence of a 6-substituted purine. B

Lipase-catalyzed monoprotection of 1,4-diols in an organic solvent using vinyl benzoate as acyl transfer agent

Lipase from Mucor miehei (MML) has been selected as the most suitable enzyme to catalyze the efficient monobenzoylation of 1,4-diols using vinyl benzoate as acyl transfer reagent in tert-butyl methyl ether. The regioselectivity of the monobenzoylation of

Photodecarbonylation of chiral cyclobutanones

Triplet photosensitized irradiation of 2(S),3(R)-bis[(benzoyloxy)methyl]cyclobutanone gave optically pure (-)E-1(S),2(S)-bis(benzoyloxymethyl)cyclopropaneas a major product in the nonpolar fraction along with its stereoisomer and cycloelimination products. The absolute stereochemistry of the chiral cyclopropane was established by independent synthesis and X-ray crystal structure determination of a synthetic precursor. The distribution of decarbonylation and cycloelimination products was inversely dependent on the concentration of the substrate. Irradiation of the same ketone in tetrahydrofuran or benzene gave mostly cycloelimination products. Addition of Michler's ketone increased the ratio of photodecarbonylation, suggesting a triplet state pathway for this process. This was corroborated by the addition of dicyanoethylene, which showed significant quenching of photodecarbonylation. Irradiation of 2(S)-[(benzoyloxy)methyl]cyclobutane in acetone gave the corresponding cyclopropane as the principal product.

A novel approach toward the synthesis of chiral 2,3-dideoxy nucleosides and their carbocyclic analogues

Photochemical ring-expansion of chiral 2(S),3(R)-bis [(benzoyloxy)methyl]cyclobutanone (3) in the presence of alcohols and acidic N-H functional groups gives anomeric mixtures of acetals and N-amino acetals, respectively, with retention of stereochemistry

A novel approach towards 2,3-dideoxyriboside synthesis

A short synthesis of 2,3-dideoxy-3(S)-C-hydroxymethyl rebosides is described. The key step involves a photochemical ring-expansion of a chiral cyclobutanone which occurs stereospecifically.