147252-93-5

Upstream product

• 147252-92-4 (2R,4S)-5,5-dimethyl-2-phenyl-4-vinyl-1,3-dioxane 
• 277317-84-7 (2R/S,3R)-3-(Benzyloxy)tetrahydro-4,4-dimethylfuran-2-ol 
• 19493-09-5 Methylenetriphenylphosphorane 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 20374-33-8 (R)-(+)-3-(Benzyloxy)-4,5-dihydro-4,4-dimethyl-furan-2(3H)-on 
• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 
• 599-04-2 (R)-Pantolacton 
• 147331-80-4 (3R)-dihydro-4,4-dimethyl-3-(2-tetrahydropyranyloxy)-2(3H)-furanone 
• 60856-63-5 (2R)-(-)-3,3-dimethylbutane-1,2,4-triol 
• 100-52-7 benzaldehyde 
• 147252-90-2 (2R,4R)-4-hydroxymethyl-5,5-dimethyl-2-phenyl-1,3-dioxane 
• 55-21-0 benzimidate 
• 100-39-0 benzyl bromide 
• 147252-91-3 (2R,4R)-4-formyl-5,5-dimethyl-2-phenyl-1,3-dioxane 

Downstream Products

• 470470-82-7 ((S)-3-benzyloxy-2,2-dimethyl-pent-4-enyloxy)-tert-butyl-dimethyl-silane 
• 470470-59-8 (5S)-5-benzyloxy-4,4-dimethylhept-6-en-1-yn-3-one 
• 570371-49-2 (4S)-4-benzyloxy-3,3-dimethyl-5-hexenal 
• 570371-51-6 (3S,6RS)-3-benzyloxy-4,4-dimethyl-6-hydroxy-1-octen-7-yne 
• 570371-53-8 (S)-7-Benzyloxy-4-hydroxy-6,6-dimethyl-1-phenyl-non-8-en-2-yn-1-one 
• 570371-55-0 (7S)-7-benzyloxy-6,6-dimethyl-1-phenylnon-8-en-2-yne-1,4-dione 
• 570371-57-2 ethyl 4-((3S)-3-benzyloxy-2,2-dimethyl-pent-4-en-1-yl)-2-ethoxy-5(Z)-benzoylmethylidene-1,3-cyclopentadiene-1-carboxylate 
• 570371-60-7 ethyl 4-((3S)-3-benzyloxy-2,2-dimethyl-pent-4-en-1-yl)-2-ethoxy-5(E)-benzoylmethylidene-1,3-cyclopentadiene-1-carboxylate 
• 570371-58-3 ethyl (1R,4S,5R,7S)-4-benzyloxy-8-ethoxy-3,3-dimethyl-10(Z)-benzoylmethylidene-tricyclo[5.2.1.0^1,5]dec-8-ene-7-carboxylate 
• 1262295-44-2 (5S,7S)-7-benzyloxy-9-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-8,8-dimethyl-nonan-3-one 
• 1262295-46-4 [(S)-3-benzyloxy-4-((4R,6R)-6-ethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-2,2-dimethyl-butoxy]-tert-butyl-dimethyl-silane 
• 1262295-47-5 (S)-3-benzyloxy-4-((4R,6R)-6-ethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-2,2-dimethyl-butan-1-ol 
• 1262295-48-6 (S)-3-benzyloxy-4-((4R,6R)-6-ethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-2,2-dimethyl-butyraldehyde 
• 1262295-41-9 (E)-(S)-5-benzyloxy-6-((4R,6R)-6-ethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-4,4-dimethyl-hex-2-enoic acid ethyl ester 

Relevant academic research and scientific papers

Formal total synthesis of cyanolide a

Formal total synthesis of cyanolide A, aglycosidic dimeric macrolide is accomplished. The key reactions involved are asymmetric acetate aldol reaction, CBS reduction, and Shiina's lactonization.

Synthesis of molluscicidal agent cyanolide a macrolactone from D-(-)-Pantolactone

An efficient synthesis of potent molluscicidal agent cyanolide A, a glycosidic 16-membered macrolide, starting from D-(-)-pantolactone is reported. Highly stereoselective aldol, oxa-Michael addition, and Yamaguchi macrolactonization are the key steps in the present synthesis.

Synthesis of 2,6-cis-disubstituted 4-methylenetetrahydropyrans by oxy-Michael addition

The combination of an 'ene' reaction between a 2-(2-trialkylsilyloxyalkyl) prop-2-enyl(trimethyl)silane and an alk-1-yn-3-one mediated by zinc(II) iodide, and an intramolecular oxy-Michael reaction, provides an efficient synthesis of cis-2,6-disubstituted 4-methylenetetrahydropyrans of interest in the context of a synthesis of bryostatins. The stereoselective formation of (E)-vinylsilanes in the 'ene' reaction is of interest.

Thermal intramolecular cycloaddition of 4-alkenylfulvene; Highly regio- and diastereoselective formation of [4+2] adduct

4-Alkenylfulvenes were prepared by the annulation of 1,4-ynediones and allylidenetriphenylphosphorane and subjected to a thermal reaction. Highly regio- and stereoselective [4+2] cycloaddition is accomplished with 4-((R)-3-benzyloxypent-4-en-1-yl)fulvene and the resulting adduct is transformed into bicyclo[3.3.0]octene derivative.

Synthesis of the C(1)-C(16) fragment of bryostatins

A synthesis of the C(1)-C(16) fragment 43 of the bryostatins is reported which features a stereoselective equivalent of an 'ene' reaction between the allylsilane 35 and the alkynone 33 and the stereoselective conjugate addition-cyclisation of the dienyl k

A ring closing metathesis-osmylation approach to oxygenated oxepanes as carbohydrate surrogates

A ring closing metathesis (RCM)-osmylation sequence has been developed for the formation of highly oxygenated cyclic ethers from the corresponding acyclic dienes. A systematic examination of various substrates in this reaction revealed that the process is general in scope and is insensitive to the number of alkoxy substituents present. Subsequent osmylation of the metathesis product proceeds with excellent diastereoselectivity to furnish highly oxygenated oxepanes. These oxepanes represent one-carbon homologated carbohydrates.

Chiral preparation of (R)- and (S)-3-(benzyloxy)-4,4-dimethyl-1-pentene

Facile routes for the preparation of an optically active allylic ether bearing the tert-butyl group at an allylic chiral center, i.e. 2-(benzyloxy)-3,3-dimethyl-1-pentene, in both (R)- and (S)-enantiomeric forms, which are expected to be promising, effici