112348-04-6

Upstream product

• 100-39-0 benzyl bromide 
• 112635-76-4 (S)-ethyl 3,4-dihydroxybutanoate 
• 60656-87-3 benzyloxyacetoaldehyde 
• 691-84-9 Diethyl (S)-malate 
• 18295-66-4 1-ethoxy-1-(trimethylsiloxy)ethene 
• 67354-34-1 ethyl 4-benzyloxyacetoacetate 

Downstream Products

• 147849-64-7 tert-butyl (S)-6-(benzyloxy)-5-hydroxy-3-oxohexanoate 
• 632357-76-7 2,2-dimethyl-propionic acid 2-{6-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-ethyl ester 
• 398516-83-1 2,2-Dimethyl-propionic acid 2-[(2S,3S,4R,6S)-6-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-3-(2-hydroxy-ethyl)-3-methyl-tetrahydro-pyran-2-yl]-ethyl ester 
• 398516-85-3 2,2-Dimethyl-propionic acid 2-[(2S,3S,4R,6S)-6-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxymethyl-3-methyl-tetrahydro-pyran-2-yl]-ethyl ester 
• 632357-77-8 2,2-Dimethyl-propionic acid 2-[(2S,3S,4R,6S)-6-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-3-vinyl-tetrahydro-pyran-2-yl]-ethyl ester 
• 632357-75-6 2,2-Dimethyl-propionic acid 2-((4aS,5S,7S,8aR)-7-benzyloxymethyl-2,2,4a-trimethyl-hexahydro-1,6-dioxa-2-sila-naphthalen-5-yl)-ethyl ester 
• 398516-81-9 2,2-Dimethyl-propionic acid 2-[(2S,3R,4R,6S)-6-benzyloxymethyl-4-hydroxy-3-(2-hydroxy-ethyl)-3-methyl-tetrahydro-pyran-2-yl]-ethyl ester 
• 632357-43-8 2,2-Dimethyl-propionic acid 2-((4aS,5S,7S,8aR)-7-benzyloxymethyl-2,2,4a-trimethyl-tetrahydro-pyrano[4,3-d][1,3]dioxin-5-yl)-ethyl ester 
• 398516-80-8 ((4aS,5S,7S,8aR)-7-Benzyloxymethyl-2,2,4a-trimethyl-hexahydro-1,6-dioxa-2-sila-naphthalen-5-yl)-acetic acid ethyl ester 
• 632357-73-4 2,2-Dimethyl-propionic acid 2-((2S,3R,4R,6S)-6-benzyloxymethyl-4-hydroxy-3-hydroxymethyl-3-methyl-tetrahydro-pyran-2-yl)-ethyl ester 
• 398516-77-3 (2S,4R)-1-Benzyloxy-4-(4-methoxy-benzyloxy)-5-methyl-hex-5-en-2-ol 
• 398516-79-5 (E)-3-((1S,3R)-1-Benzyloxymethyl-3-hydroxy-4-methyl-pent-4-enyloxy)-acrylic acid ethyl ester 
• 632357-74-5 (2S,4R)-1-Benzyloxy-5-methyl-hex-5-ene-2,4-diol 
• 398516-72-8 (S)-6-Benzyloxy-5-hydroxy-2-methyl-hex-1-en-3-one 

Relevant academic research and scientific papers

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.

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

Process for preparing optically active oxazolidinone derivative

Disclosed is a process for preparing an optically active oxazolidinone derivative comprising allowing hydrazine to react on an optically active ester having a hydroxyl group at the 3-position which is represented by formula (II): wherein R1represents a lower alkyl group having 1 to 4 carbon atoms, a phenyl group, a methoxymethyl group, a benzyloxymethyl group, a benzyloxycarbonylaminomethyl group which may have a substituent or substituents on the benzene ring thereof, an acylaminomethyl group having 3 to 10 carbon atoms, or an alkyloxycarbonylaminomethyl group having 3 to 6 carbon atoms; R2and R3, which may be the same or different, each represent a hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms, a phenyl group, an acetylaminomethyl group, a benzoylaminomethyl group, or a benzyl group; and * indicates an asymmetric carbon atom, and subjecting the resulting hydrazide to Curtius rearrangement.

Lasonolide A: Structural revision and synthesis of the unnatural (-)-enantiomer

Total synthesis of the unnatural (-)-enantiomer of lasonolide A was achieved starting from ethyl l-malate. The two tetrahydropyranyl fragments were prepared stereoselectively via radical cyclization reactions of β-alkoxyacrylates. The full structure of na

C2-Symmetric Cu(II) Complexes as Chiral Lewis Acids. Catalytic, Enantioselective Cycloadditions of Silyl Ketenes

(matrix presented) C2-Symmetric bis(oxazoline)-Cu(II) complexes (4a-g) catalyze the enantioselective [2 + 2] cycloaddition between (silyl)ketenes and chelating carbonyl substrates. A range of substituted β-lactones can be produced in excellent yields and selectivities. It was also found that (trimethylsilyl)-ketene (1) may also undergo a highly selective hetero Diels-Alder reaction with β,γ-unsaturated α-keto esters.

C2-symmetric copper(II) complexes as Chiral Lewis acids. Scope and mechanism of catalytic enantioselective aldol additions of enolsilanes to (benzyloxy)acetaldehyde

C2-Symmetric bis(oxazolinyl)pyridine (pybox)-Cu(II) complexes have been shown to catalyze enantioselective Mukaiyama aldol reactions between (benzyloxy)acetaldehyde and a variety of silylketene acetals. The aldol products are generated in high yields and in 92-99% enantiomeric excess using as little as 0.5 mol % of chiral catalyst [Cu((S,S)-Ph-pybox)](SbP6)2. With substituted silylketene acetals, syn reaction diastereo-selection ranging from 95:5 to 97:3 and enantioselectivities ≥95% are observed. Investigation into the reaction mechanism utilizing doubly labeled silylketene acetals indicates that the silyl-transfer step is intermolecular. Further mechanistic studies revealed a significant positive nonlinear effect, proposed to arise from the selective formation of the [Cu((S,S)-Ph-pybox)((R,R)-Ph-pybox)](SbF6)2 2:1 ligand:metal complex. A stereochemical model is presented in which chelation of (benzyloxy)acetaldehyde to the metal center to form a square pyramidal copper intermediate accounts for the observed sense of induction. Support for this proposal has been obtained from double stereodifferentiating reactions, EPR spectroscopy, ESI spectrometry, and, ultimately, the X-ray crystal structure of the aldehyde bound to the catalyst. The C2-symmetric bis(oxazolinyl)-Cu(II) complex [Cu((S,S)-tert-Bu-box)](OTf)2 is also an efficient catalyst for the aldol reaction, but the scope with this system is not as broad.

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.

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.

(3R,5S)-3,5,6-trihydroxyhexanoic acid derivative and production method thereof

A (3R,5S)-3,5,6-trihydroxyhexanoic acid derivative and a process of producing the (3R,5S)-3,5,6-trihydroxyhexanoic acid derivative which comprises the step of enantioselectively hydrogenating an (S)-5,6-dihydroxy-3-oxohexanoic acid derivative with a speci