147849-60-3

Upstream product

• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 
• 90414-36-1 methyl (3S)-3,4-dihydroxybutyrate 
• 36850-80-3 [(1-methoxyvinyl)oxy]trimethylsilane 
• 60656-87-3 benzyloxyacetoaldehyde 
• 32122-09-1 ethyl benzyloxyacetate 
• 2930-05-4 (S)-benzyl glycidyl ether 
• 67-56-1 methanol 
• 87938-77-0 3-<(benzyloxy)methyl>oxirane-2-carboxaldehyde 
• 82961-76-0 4-benzyloxy-3-oxobutyric acid methyl ester 
• 95967-46-7 tert-Butyl 4-benzyloxy-3-oxobutanoate 
• 5418-86-0 tris(methylthio)methane 
• 14618-80-5 (R)-benzyl glycidol 
• 201230-82-2 carbon monoxide 
• 147849-59-0 tert-Butyl (S)-4-benzyloxy-3-hydroxybutanoate 

Downstream Products

• 191408-24-9 2R,3S-Methyl 4-benzyloxy-3-hydroxy-2-(2E-3-phenyl-2-propen-1-yl)butyrate 
• 153255-54-0 (4R,6R)-6-Benzyloxymethyl-4-hydroxy-tetrahydro-pyran-2-one 
• 92757-18-1 (4R,6S)-6-(benzyloxy)methyl-4-hydroxy-tetrahydro-2-pyrone 
• 124662-66-4 (6S)-6-[(phenylmethoxy)methyl]-5,6-dihydro-2H-pyran-2-one 
• 120996-46-5 (R)-6-Benzyloxymethyl-5,6-dihydro-2-pyrone 
• 191408-40-9 ((S)-4-{(E)-(R)-2-[(S)-2-Benzyloxy-1-(2-bromomethyl-allyloxy)-ethyl]-5-phenyl-pent-4-enoylamino}-4-methylcarbamoyl-butyl)-carbamic acid tert-butyl ester 
• 191408-27-2 ((S)-4-{(E)-(R)-2-[(S)-2-Benzyloxy-1-((E)-4-bromo-but-2-enyloxy)-ethyl]-5-phenyl-pent-4-enoylamino}-4-methylcarbamoyl-butyl)-carbamic acid tert-butyl ester 
• 191408-42-1 (2S,3R,6S)-10-Acetyl-2-benzyloxymethyl-12-methylene-4-oxo-3-((E)-3-phenyl-allyl)-1-oxa-5,10-diaza-cyclotridecane-6-carboxylic acid methylamide 
• 191408-26-1 {(S)-4-[(E)-(R)-2-((S)-2-Benzyloxy-1-hydroxy-ethyl)-5-phenyl-pent-4-enoylamino]-4-methylcarbamoyl-butyl}-carbamic acid tert-butyl ester 
• 191408-25-0 2R,3S-4-Benzyloxy-3-hydroxy-2-(2E-3-phenyl-2-propen-1-yl)butyric acid 
• 141942-99-6 (S)-4-(Benzyloxy)-3-hydroxybutanoic acid 
• 147849-64-7 tert-butyl (S)-6-(benzyloxy)-5-hydroxy-3-oxohexanoate 
• 147849-63-6 tert-butyl (5R)-3-oxo-5-hydroxy-6-benzyloxyhexanoate 

Relevant academic research and scientific papers

An improved reaction of tris(methylthio)methane with epoxides: Application to the efficient synthesis of β-hydroxy esters

Tris(methylthio)methyllithium reacts efficiently with epoxides in THF:HMPA (5:1) at low temperature to give β-hydroxy orthotrithiocarboxylates which are converted to β-hydroxy esters in high yield.

A new class of tunable dendritic diphosphine ligands: Synthesis and applications in the Ru-catalyzed asymmetric hydrogenation of functionalized ketones

A series of tunable G0-G3 dendritic 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP) ligands was prepared by attaching polyaryl ether dendrons onto the four phenyl rings on the P atoms. Their ruthenium complexes were employed in the asymmetric hydrogenation of β-ketoesters, α-ketoesters, and α-ketoamides to reveal the effects of dendron size on the catalytic properties. The second- and third-generation catalysts exhibited excellent enantioselectivities, which are remarkably higher than those obtained from the small molecular catalysts and the first-generation catalyst. Molecular modeling indicates that the incorporation of bulky dendritic wedges can influence the steric environments around the metal center. In addition, the ruthenium catalyst bearing a second-generation dendritic ligand could be recycled and reused seven times without any obvious decrease in enantioselectivity.

Enantio- and diastereoselective hetero-Diels-Alder reactions between 2-aza-3-silyloxy-1,3-butadienes and aldehydes catalyzed by chiral dirhodium(ii) carboxamidates

The first catalytic asymmetric hetero-Diels-Alder reaction between 2-aza-3-silyloxy-1,3-butadienes and aldehydes is described. With dirhodium(ii) tetrakis[N-benzene-fused-phthaloyl-(S)-piperidinonate], Rh2(S-BPTPI) 4, the cycloaddition reaction proceeded exclusively in an endo mode to give all-cis-substituted 1,3-oxazinan-4-ones in high yields with up to 98% ee.

Organocatalytic preparation of simple β-hydroxy and β-amino esters: Low catalyst loadings and gram-scale synthesis

A combined amino- and N-heterocyclic carbene (NHC)-catalyzed one-pot reaction sequence for the synthesis of simple enantioenriched β-hydroxy and β-amino esters using commercially available catalysts at low catalyst loadings has been developed. The desired

The Mukaiyama aldol and Mukaiyama-Michael reactions promoted by commercially available molecular sieves

The Mukaiyama aldol reaction of silyl ketene acetals with aldehydes has been effected by using commercially available 4 molecular sieves (4 MS) as a promoter. Various silyl ketene acetals and silyl enol ethers have been shown to be effective nucleophiles

An improved asymmetric Reformatsky reaction mediated by (-)-N,N-dimethylaminoisoborneol

(-)-N,N-Dimethylaminoisoborneol ((-)-DAIB) was found to be an excellent ligand for the enantioselective addition of Reformatsky reagents to aromatic and aliphatic aldehydes. Enantioselectivities up to 93% ee were obtained with sulfur-containing aldehydes.

Dirhodium(II) tetrakis[N-benzene-fused phthaloyl-(S)-piperidinonate] as a chiral lewis acid: Catalytic enantioselective aldol reactions of acetate-derived silylketene acetals and aldehydes

A first example of chiral dirhodium(II) complex-catalyzed enantioselective Mukaiyama aldol reactions is described. The aldol addition reaction of methyl acetate-derived trimethylsilylketene acetal with specific aldehydes such as benzyloxyacetaldehyde and electron-poor aromatic aldehydes is effectively catalyzed by dirhodium(II) tetrakis[N-benzene-fused phthaloyl-(S)-piperidinonate] (1a), providing silylated aldol adducts in up to 94% ee.

P1, P2'-linked macrocyclic amine derivatives as matrix metalloproteinase inhibitors

A novel series of 13- and 14-membered macrocyclic amines was developed by linking the P1 and P2' groups. The synthesis entails stereoselective Frater alkylation to install the anti-succinate configuration and macrocyclic amination via nucleophilic displacement. This strategy resulted in a new class of conformationally constrained inhibitors that are potent and selective for MMP-8 and 9 over MMP-1 and 3.

Preparation of 12- and 16-membered macrolactones (oligolides) from (S)-malic acid - Low molecular-mass analogs of the biopolymer Poly[(S)-Malic Acid] (PMA)

As model compounds of uniform composition for the biopolymer PMA, 12- and 16-membered oligolides derived from malic acid by esterification between the carboxylic acid and the β-hydroxy groups were prepared (Schemes 1 and 2). A reduced form of the triolide derivatives 2, 4, the tris(hydroxymethyl) triolide 10, was also synthesized (Scheme 3). The macrocyclic compounds were isolated in up to 60% yield and fully characterized. The water-soluble tri- and tetracarboxylic acids of this type, thus available for the first time, will be studied as potential binders to polycationic biomolecules. VCH Verlagsgesellschaft mbH, 1996.

Asymmetric Hydrogenation of 3,5-Dioxoesters Catalyzed by Ru-binap Complex: A Short Step Asymmetric Synthesis of 6-Substituted 5,6-dihydro-2-pyrones

Asymmetric hydrogenation of 3,5-dioxoesters 1a-c using Ru2Cl4((R) or (S)-binap)2(NEt3) as the catalyst gave dominantly anti 3,5-dihydroxyesters 2, which were then converted into unsaturated lactones 5a-b (ca. 80percent e.e.).The pathway of the hydrogenation reaction was also investigated by asymmetric hydrogenation of (R)- or (S)-5-hydroxy-3-oxoesters 8a-c.It was revealed that the Ru-binap catalyzed hydrogenation of 1a-b proceed dominantly via the β-diketone mode.A convenient asymmetric synthesis of hydroxylactone 3c and unsaturated lactone 5c was presented.Key words: 3,5-dioxoester; Ru-binap catalyst; asymmetric hydrogenation; asymmetric synthesis; lactone