635758-46-2

Basic information

• Product Name: 2-Oxazolidinone, 3-[(2E)-2-methyl-1-oxo-2-pentenyl]-4-(phenylmethyl)-, (4S)-
• CAS NO: 635758-46-2
• Molecular Formula: C16H19NO3
• Molecular Weight: 273.332
• Mol File: 635758-46-2.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 2-Oxazolidinone, 3-[(2E)-2-methyl-1-oxo-2-pentenyl]-4-(phenylmethyl)-, (4S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Oxazolidinone, 3-[(2E)-2-methyl-1-oxo-2-pentenyl]-4-(phenylmethyl)-, (4S)-(635758-46-2)
• EPA Substance Registry System: 2-Oxazolidinone, 3-[(2E)-2-methyl-1-oxo-2-pentenyl]-4-(phenylmethyl)-, (4S)-(635758-46-2)

Safety Data

• Hazardous Substances Data: 635758-46-2(Hazardous Substances Data)

Upstream product

• 90719-32-7 (S)-4-Benzyl-2-oxazolidinone 
• 16957-70-3 2-methylpent-2-enoic acid 

Downstream Products

• 947231-50-7 (S)-4-benzyl-3-[(R,E)-2-(3,3-dimethoxypropylthio)-2-methylpent-3-enoyl]oxazolidin-2-one 
• 1202363-22-1 (S)-4-benzyl-3-[(RS,E)-4-(3,3-dimethoxypropylthio)-2-methylpent-2-enoyl]oxazolidin-2-one 
• 1202363-20-9 (S)-4-benzyl-3-[(S,E)-2-(3,3-dimethoxypropylthio)-2-methylpent-3-enoyl]oxazolidin-2-one 
• 1403991-96-7 (S)-4-benzyl-3-((4S,5R,E)-5-(tert-butyldimethylsilyloxy)-2,4-dimethylhept-2-enoyl)oxazolidin-2-one 
• 74758-60-4 protylonolide 
• 58947-83-4 12,13-de-epoxy-12,13-dehydro-20-dihydrorosaramicin 
• 56689-42-0 12,13-de-epoxy-12,13-didehydrorosaramicin 
• 59227-84-8 20-deoxo-20-dihydrorosaramicin 
• 35834-26-5 rosaramicin 
• 80240-61-5 5-O-desosaminyltylonolide 
• 1403991-98-9 (S)-3-((E,4S,5R)-5-hydroxyl-2,4-dimethylhept-2-enoyl)-4-benzyloxazolidin-2-one 
• 947231-77-8 (R,E)-benzyl 2-methyl-2-(acetylthio)pent-3-enoate 
• 947231-69-8 (R,E)-benzyl 2-methyl-2-(propionylthio)pent-3-enoate 
• 947231-63-2 (R,E)-benzyl 2-methyl-2-(3-oxopropylthio)pent-3-enoate 

Relevant articles and documents

Chemoenzymatic Total Synthesis and Structural Diversification of Tylactone-Based Macrolide Antibiotics through Late-Stage Polyketide Assembly, Tailoring, and C-H Functionalization

Polyketide synthases (PKSs) represent a powerful catalytic platform capable of effecting multiple carbon-carbon bond forming reactions and oxidation state adjustments. We explored the functionality of two terminal PKS modules that produce the 16-membered tylosin macrocycle, using them as biocatalysts in the chemoenzymatic synthesis of tylactone and its subsequent elaboration to complete the first total synthesis of the juvenimicin, M-4365, and rosamicin classes of macrolide antibiotics via late-stage diversification. Synthetic chemistry was employed to generate the tylactone hexaketide chain elongation intermediate that was accepted by the juvenimicin (Juv) ketosynthase of the penultimate JuvEIV PKS module. The hexaketide is processed through two complete modules (JuvEIV and JuvEV) in vitro, which catalyze elongation and functionalization of two ketide units followed by cyclization of the resulting octaketide into tylactone. After macrolactonization, a combination of in vivo glycosylation, selective in vitro cytochrome P450-mediated oxidation, and chemical oxidation was used to complete the scalable construction of a series of macrolide natural products in as few as 15 linear steps (21 total) with an overall yield of 4.6%.

Synthesis and biological activity of enantiomeric pairs of 5-vinylthiolactomycin congeners

Twelve enantiomeric pairs of 5-vinylthiolactomycin congeners were synthesized by employing our efficient synthetic route previously explored for the synthesis of enantiomeric pairs of thiolactomycin and its 3-demethyl derivative. From the biological activ