303727-83-5

Basic information

• Product Name: (-)-(R)-4-benzyl-3-((2R,3S,4S)-3-hydroxy-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentanoyl)oxazolidin-2-one
• Synonyms: (-)-(R)-4-benzyl-3-((2R,3S,4S)-3-hydroxy-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentanoyl)oxazolidin-2-one
• CAS NO: 303727-83-5
• Molecular Weight: 441.524
• Mol File: 303727-83-5.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: (-)-(R)-4-benzyl-3-((2R,3S,4S)-3-hydroxy-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentanoyl)oxazolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-(R)-4-benzyl-3-((2R,3S,4S)-3-hydroxy-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentanoyl)oxazolidin-2-one(303727-83-5)
• EPA Substance Registry System: (-)-(R)-4-benzyl-3-((2R,3S,4S)-3-hydroxy-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentanoyl)oxazolidin-2-one(303727-83-5)

Safety Data

• Hazardous Substances Data: 303727-83-5(Hazardous Substances Data)

Upstream product

• 132969-60-9 (2S)-3-[(4-methoxybenzyl)oxy]-2-methylpropanal 
• 101711-78-8 (3R)-3-propionyl-4-benzyloxazolidin-2-one 
• 89238-99-3 O-(4-methoxybenzyl)-trichloroacetimidate 
• 132969-71-2 methyl (2S)-[(4-methoxybenzyl)oxy]-2-methylpropanoate 
• 136320-64-4 (2R)-3-[(4-methoxybenzyl)oxy]-2-methylpropanol 
• 60669-69-4 di-n-butylboryl trifluoromethanesulfonate 
• 40217-17-2 (R)-4-(phenylmethyl)-2-oxazolidinone 

Downstream Products

• 1256166-28-5 (R)-3-((2R,3S,4S)-5-(4-methoxybenzyloxy)-3-(methoxymethoxy)-2,4-dimethylpentanoyl)-4-benzyloxazolidin-2-one 
• 40217-17-2 (R)-4-(phenylmethyl)-2-oxazolidinone 
• 252342-49-7 (2R,3S,4S)-3-hydroxy-5-(4-methoxybenzyloxy)-2,4-dimethylpentanoic acid methoxymethylamide 
• 398518-77-9 (2R,3S,4S)-3-hydroxy-5-(4-methoxybenzyloxy)-2,4-dimethylpentanoic acid 
• 496035-38-2 (+)-tert-butyl-{(S)-2-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]propoxy}dimethylsilane 
• 496035-39-3 (+)-(2S,3S,4S)-5-(tert-butyldimethylsilanyloxy)-3-(4-methoxybenzyloxy)-2,4-dimethylpentan-1-ol 
• 261968-20-1 (-)-(2R,3R,4S)-5-(tert-butyldimethylsilanyloxy)-3-(4-methoxybenzyloxy)-2,4-dimethylpentanal 
• 184291-96-1 (+)-tert-butyl-[(Z)-(2S,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethylocta-5,7-dienyloxy]dimethylsilane 
• 184291-36-9 (+)-(Z)-(2S,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethylocta-5,7-dien-1-ol 
• 184291-97-2 (+)-(Z)-(2R,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethylocta-5,7-dienal 
• 303727-87-9 (2R,3S,4S)-3-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2,4-dimethyl-pentanoic acid N-methoxy-N-methyl-amide 

Relevant articles and documents

Nhatrangin A: Total Syntheses of the Proposed Structure and Six of Its Diastereoisomers

A total synthesis of the proposed structure of nhatrangin A is described. This strategy relies on two aldol reactions to install the chiral centers at C3/C4 and C3′/C4′, a lithium-mediated coupling between an advanced intermediate alkyne and a Weinreb amide to complete the C1-C13 alkyl scaffold, and a Yamaguchi esterification to set the side chain. Discrepancies in the spectroscopic data between synthetic and natural nhatrangins led us to synthesize six more diastereoisomers of the proposed structure of nhatrangin A.

Probing o-diphenylphosphanyl benzoate (o-DPPB)-directed C - C bond formation: Total synthesis of dictyostatin

Herein, we report a robust total synthesis of dictyostatin. This polyketide natural product has attracted much attention because of its impressive antiproliferative activity against several human cancer-cell lines. We accomplished its synthesis in a highly convergent manner from three fragments of equal complexity, which were prepared on multigram scale. The southern and northwestern subunits were constructed through application of our o-DPPB-directed hydroformylation and allylic substitution methodology, respectively. These methods generated the C6 and C14 stereocenters of dictyostatin with good diastereoselectivities and simultaneously allowed further elaboration of the fragments by Wittig olefination and Sharpless asymmetric epoxidation, respectively. The compelling performance of the hydroformylation and allylic substitution with regard to practicability, selectivity, and scale underline their value for the construction of propionate motifs.

A practical approach to synthesize the C(9)-C(24) fragment of (+)-discodermolide

A practical and stereoselective synthesis of the C(9)-C(24) subunit of (+)-discodermolide has been achieved. The strategy featured the construction of the key intermediate Z-trisubstituted vinyl iodide 12 from the dibromoolefin 6 via an efficient modified