106058-91-7

Upstream product

• 67354-34-1 ethyl 4-benzyloxyacetoacetate 
• 100-39-0 benzyl bromide 
• 112635-76-4 (+)-(R)-ethyl 3,4-dihydroxybutanoate 
• 18295-66-4 1-ethoxy-1-(trimethylsiloxy)ethene 
• 60656-87-3 benzyloxyacetoaldehyde 
• 7554-28-1 diethyl (R)-malate 
• 172424-23-6 ethyl 4-(benzyloxy)-2-chloro-3-oxobutanoate 

Downstream Products

• 733000-60-7 (S)-2-((R)-2-Benzyloxy-1-hydroxy-ethyl)-5-methyl-hex-4-enoic acid ethyl ester 
• 549502-23-0 (3S,5R)-6-benzyloxy-3,5-dihydroxy-hexanoic acid tert-butyl ester 
• 215876-09-8 (3R,5R)-6-benzyloxy-3,5-dihydroxy-hexanoic acid tert-butyl ester 
• 515816-12-3 (E)-3-[(1R,3S)-1-Benzyloxymethyl-3-(bromomethyl-dimethyl-silanyloxy)-4-methyl-pent-4-enyloxy]-acrylic acid ethyl ester 
• 515816-15-6 ((4aR,5R,7R,8aS)-7-Benzyloxymethyl-2,2,4a-trimethyl-hexahydro-1,6-dioxa-2-sila-naphthalen-5-yl)-acetic acid ethyl ester 
• 733000-65-2 (S)-5-[(R)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-methyl-tetradec-2-en-6-one 

Relevant academic research and scientific papers

Control of enantioselectivity in the bakers' yeast reduction of β-keto ester derivatives in the presence of a sulfur compound

Improvement of the enantioselectivity and enhancement of the reactivity were achieved in the bakers' yeast reduction of the β-keto ester derivatives by the addition of a sulfur compound.

The bakers' yeast reductions of α- and β-keto ester derivatives in the presence of a sulfur compound

Improvement of the enantioselectivity and enhancement of the reactivity were achieved in the bakers' yeast reduction of the α- and β-keto ester derivatives by the addition of a sulfur compound. High enantioselectivity in the bakers' yeast reduction of keto esters was accomplished by using combination of an addition of a sulfur compound with an appropriate selection of the alcohol part of the ester.

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.

Production method of hexahydrofurofuranol derivative, intermediate therefor and production method thereof

The present invention provides a method for producing compound (XIV) useful as an intermediate for pharmaceutical agents efficiently and economically on an industrial scale without using ozone oxidation and highly toxic reagent, and an intermediate used for this method. Particularly, the present invention provides a method for producing a compound having an absolute configuration represented by the formula (XV) and an enantiomer thereof without using a technique such as optical resolution and the like, and an intermediate used for this method. (1) Compound (XIII) as a starting material is led to compound (I), and after introducing a protecting group, subjected to reduction and cyclization to give compound (XIV). Particularly, compound (XIII) as a material is led to compound (I) via compound (XX) to produce compound (XIV). Using an optically active compound (XIII) as a starting material, a compound having an absolute configuration represented by the formula (XV) and the like are produced highly stereoselectively. (2) Compound (XXI) as a starting material is stereoselectively reduced to give compound (XXII), and by introduction of a protecting group, reduction and cyclization, compound (XXVI) is obtained, and by inverting hydroxyl group, compound (XV) is produced. wherein each symbol is as defined in the specification.

An efficient ruthenium-catalyzed formal synthesis of (-)-isoavenaciolide

A formal synthesis of (-)-isoavenaciolide (1) by two different routes is reported. The first approach, leading to a key precursor 2 of (-)-isoavenaciolide (1), features the stereoselective construction of the three contiguous stereogenic centers by Evans

Process for producing optically active gamma-butyrolactone

This invention provides a novel process for producing optically active 3-hydroxy-γ-butyrolactone in a short step, which is superior economically and in efficiency and industrially suitable by using a starting material which is inexpensive and easily available and reagents easy to handle. This invention relates to a process for producing optically active 3-hydroxy-γ-butyrolactone represented by formula I: wherein the symbol * means an asymmetric carbon atom, which comprises hydrogenating an optically active 4-substituted oxy-3-hydroxybutyrate represented by formula II: wherein R1 represents a C1-4 lower alkyl group, R2 represents a protective group for a hydroxyl group deprotected by hydrogenation with a heterogeneous hydrogenation catalyst, and the symbol * has the same meaning as defined above, in the presence of a heterogeneous hydrogenation catalyst and an acidic substance followed by deprotection and simultaneous ring closure thereof.

Lasonolide A: Structural revision and total synthesis

The proposed structure of lasonolide A was synthesized employing radical cyclization reactions of β-alkoxyacrylates for preparation of the tetrahydropyranyl units A and B, but the spectroscopic data did not match those of the natural product. Both enantio

New Chiral Diphosphine Ligands Designed to Have a Narrow Dihedral Angle in the Biaryl Backbone

A series of novel optically active diphosphine ligands, (4,4′-bi-1,3-benzodioxole)-5,5′-diylbis(diarylphosphine)s (6), which are called SEGPHOS, has been designed and synthesized with dihedral angles in the Ru complexes being less than that in the corresponding BINAP-Ru complex. The stereorecognition abilities of SEGPHOS-Ru complex catalysts in the asymmetric catalytic hydrogenation of a wide variety of carbonyl compounds are superior to those observed with BINAP-Ru complex catalysts.

The microbial reduction of 2-chloro-3-oxoesters

Several aliphatic or aromatic 2-chloro-3-oxoesters are stereoselectively reduced by yeast or fungal strains, affording in fair to good yield and high enantiomeric excess some of the respective 2-chloro-3-hydroxyester stereoisomers.

Studies on the Stereochemical Control of Fermenting Baker's Yeast Mediated Reductions: Some 3- and 4-Oxo Esters

Ethyl 4-benzyloxy-3-oxobutanoate (1c) is reduced by fermenting baker's yeast with stereochemical control which is dependent on the yeast: substrate ratio and the presence or absence of ethanol.Contrary to earlier reports, ethyl levulinate (3a) can be ster