150407-67-3

Basic information

• Product Name: dihydro-5(S)-(hydroxymethyl)-3(R)-(phenylmethyl)-3(2H)-furanone
• Synonyms: dihydro-5(S)-(hydroxymethyl)-3(R)-(phenylmethyl)-3(2H)-furanone
• CAS NO: 150407-67-3
• Molecular Weight: 206.241
• Mol File: 150407-67-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: dihydro-5(S)-(hydroxymethyl)-3(R)-(phenylmethyl)-3(2H)-furanone(CAS DataBase Reference)
• NIST Chemistry Reference: dihydro-5(S)-(hydroxymethyl)-3(R)-(phenylmethyl)-3(2H)-furanone(150407-67-3)
• EPA Substance Registry System: dihydro-5(S)-(hydroxymethyl)-3(R)-(phenylmethyl)-3(2H)-furanone(150407-67-3)

Safety Data

• Hazardous Substances Data: 150407-67-3(Hazardous Substances Data)

Upstream product

• 53716-82-8 1,6-anhydro-3,4-dideoxy-β-D-glycero-hexopyranos-2-ulose 
• 37112-31-5 levoglucosenone 
• 100-52-7 benzaldehyde 
• 100-39-0 benzyl bromide 
• 102717-29-3 (5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)dihydrofuran-2(3H)-one 
• 32780-06-6 (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 
• 62396-80-9 (5S)-(5-tert-butyldimethylsilyloxymethyl)furan-2(5H)-one 
• 150323-16-3 3R,5S-3-Benzyl-5-(tert-butyldiphenylsiloxymethyl)-4,5-dihydro-2(3H)-furanon 
• 172649-42-2 dihydro-5(S)-<<(tert-butyldimethylsilyl)oxy>methyl>-3(R)-(phenylmethyl)-3(2H)-furanone 

Downstream Products

• 342601-25-6 C₃₂H₃₇F₃N₄O₄ 
• 150323-33-4 dihydro-5(S)-<<<(trifluoromethyl)sulfonyl>oxy>methyl>-3(R)-(phenylmethyl)-3(2H)-furanone 
• 155720-17-5 3R,5S-5-Azidomethyl-3-benzyl-4,5-dihydro-2(3H)-furanon 
• 150323-37-8 N-(2(R)-hydroxy-1-(S)-indanyl)-2(R)-(phenylmethyl)-4(S)-<(tert-butyldimethylsilyl)oxy>-5-<1-<4-<(1,1-dimethylethoxy)carbonyl>-2(S)-(N-tert-butylcarbamoyl)piperazinyl>>pentanamide 
• 150323-20-9 (3S,4aS,8aS)-2-[(2S,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-5-phenyl-pentyl]-decahydro-isoquinoline-3-carboxylic acid tert-butylamide 
• 174139-99-2 2(R)-(phenylmethyl)-4(S)-<(tert-butyldimethylsilyl)oxy>-5-<1-<4-<(1,1-dimethylethoxy)carbonyl>-2(S)-(N-tert-butylcarbamoyl)piperazinyl>>pentanoic acid 
• 150323-19-6 (2R,4S)-2-Benzyl-5-((3S,4aS,8aS)-3-tert-butylcarbamoyl-octahydro-isoquinolin-2-yl)-4-(tert-butyl-dimethyl-silanyloxy)-pentanoic acid 
• 1027528-21-7 (S)-3-tert-Butylcarbamoyl-4-((2S,4R)-4-carboxy-2-hydroxy-5-phenyl-pentyl)-piperazine-1-carboxylic acid tert-butyl ester 
• 150323-36-7 dihydro-5(S)-<<4-<(1,1-dimethylethoxy)carbonyl>-2(S)-(N-tert-butylcarbamoyl)piperazinyl>methyl>-3(R)-(phenylmethyl)-3(2H)-furanone 
• 170902-38-2 (2R,4S)-2-Benzyl-5-((3S,4aS,8aS)-3-tert-butylcarbamoyl-octahydro-isoquinolin-2-yl)-4-hydroxy-pentanoic acid 
• 150323-18-5 (3S,4aS,8aS)-2-((2S,4R)-4-Benzyl-5-oxo-tetrahydro-furan-2-ylmethyl)-decahydro-isoquinoline-3-carboxylic acid tert-butylamide 
• 150378-17-9 indinavir 
• 150323-38-9 [14C]-N-Dealkyl Indinavir 
• 321435-46-5 (R)-3-[(2S,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((3S,4S)-3-hydroxy-chroman-4-ylcarbamoyl)-5-phenyl-pentanoyl]-5,5-dimethyl-thiazolidine-4-carboxylic acid (3,5-dimethyl-isoxazol-4-ylmethyl)-amide 

Relevant articles and documents

Efficient Synthesis of an Indinavir Precursor from Biomass-Derived (-)-Levoglucosenone

Lignocellulosic biomass pyrolysis with acid catalysis selectively produces the useful chiral synthon 6,8-dioxabicyclo[3.2.1]oct-2-ene-4-one ((-)-levoglucosenone, LGO). In this report, LGO was used to prepare (3R,5S)-3-benzyl-5-(hydroxymethyl)-4,5-dihydrofuran-2(3H)-one, which is an intermediate used in the construction of antivirals including the protease inhibitor indinavir. To achieve the synthesis, the hydrogenated derivative of LGO was functionalised using aldol chemistry and various aromatic aldehydes were used to show the scope of the reaction. Choice of base affected reaction times and the best yields were obtained using 1,1,3,3-tetramethylguanidine. Hydrogenation of the α-benzylidene-substituted bicyclic system afforded a 4:3 equatorial/axial mixture of isomers, which was equilibrated to a 97:3 mixture under basic conditions. Subsequent Baeyer-Villiger reaction afforded the target lactone in 57% overall yield for four steps, a route that avoids the protection and strong base required in the traditional approach. The aldol route is contrasted with the α-alkylation and a Baylis-Hillman approach that also both start with LGO.

Amino acids, XV: Synthesis of enantiopure DAVA-derivatives (5-amino-4-hydroxypentanoic acids) from (S)-glutamic acid

Starting from (S)-glutamic acid the readily available hydroxymethyl lactone 1 is protected as the TBDPS ether 2. Alkylation of the lithium enolate of 2 provides the lactones 3a,b with high diastereomeric excess. On the other hand 1,4 addition of Gilman cuprates to 10 furnishes the alcohols 12a,b after deprotection. Transformation of 4,12 via the mesylates 5,13 and the azides 6,14 affords the Boc protected amines 7,15 after catalytic hydrogenation in the presence of Boc2O. After treatment of 7,15 with methanolic HCl the rings of the crystalline hydrochlorides 8,16 are opened to the DAVA-derivatives (δ-aminovaleric acid derivatives) 9,17.