95112-81-5

Upstream product

• 95112-75-7 (S)-5-Benzyloxy-3-hydroxy-2-methylsulfanyl-pentanoic acid ethyl ester 
• 19790-60-4 3-Benzyloxypropanal 
• 4799-68-2 3-benzyloxypropan-1-ol 
• 64714-79-0 5-benzyloxy-3-oxo-pentanoic acid ethyl ester 
• 182417-47-6 1-ethoxy-1-(trimethylsilyloxy)-2,2-(ethylenedithio)ethene 

Downstream Products

• 142929-76-8 (2S,3S)-5-Benzyloxy-3-hydroxy-2-methyl-pentanoic acid ethyl ester 
• 142929-89-3 (2R,3S)-5-Benzyloxy-3-hydroxy-2-methyl-pentanoic acid ethyl ester 
• 777068-65-2 (S)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-pentanoic acid ethyl ester 
• 850416-19-2 (S)-5-Benzyloxy-3-methoxymethoxy-pentanoic acid ethyl ester 
• 1227307-09-6 (S,E)-5-((2S,6R)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-methylenetetrahydro-2H-pyran-2-yl)-1-(4-methoxybenzyloxy)-4-methylpent-4-en-2-ol 
• 1315318-94-5 (S)-ethyl 5-(tert-butyldiphenylsilyloxy)-3-hydroxypentanoate 
• 1345855-36-8 C₄₄H₆₄O₅Si₂ 
• 1345855-37-9 C₄₄H₆₄O₅Si₂ 
• 1315318-98-9 tert-butyl(2-((2R,6S)-4-methylene-6-vinyltetrahydro-2H-pyran-2-yl)ethoxy)diphenylsilane 
• 142929-77-9 (2R,3S)-2-methyl-1,3-O-(1-methylethylidene)-5-O-(phenylmethyl)-1,3,5-pentanetriol 
• 73814-98-9 (2R,3S)-5-Benzyloxy-2-methyl-pentane-1,3-diol 
• 198754-79-9 (3R,5S)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-heptanoic acid ethyl ester 
• 198754-78-8 (3S)-5-benzyloxy-3-(tert-butyldimethylsilyl)oxypentanal 
• 1026363-66-5 (3S,11S)-1,13-Bis-benzyloxy-5-hydroxy-3,11-bis-triethylsilanyloxy-9-trimethylsilanyloxy-tridecan-7-one 

Relevant academic research and scientific papers

Enantioselective total synthesis of (-)-zampanolide, a potent microtubule-stabilizing agent

An enantioselective total synthesis of zampanolide has been accomplished using a novel DDQ/Bronsted acid promoted cyclization as the key reaction. The synthesis features cross-metathesis to construct the trisubstituted olefin and a ring-closing metathesis

First stereoselective synthesis of the C(1)-C(13) fragment of dolabelides using ruthenium-SYNPHOS-catalyzed asymmetric hydrogenation reactions

The first stereocontrolled synthesis of the C(1)-C(13) fragment of cytotoxic macrolides dolabelides is reported. The C(3), C(7), C(9) and C(11) hydroxyl-bearing stereocenters were installed using ruthenium-mediated asymmetric hydrogenation reactions of the adequate β-keto esters and β-hydroxy ketone. Georg Thieme Verlag Stuttgart.

Formal synthesis of (-)-apicularen A

(Matrix Presented) A formal synthesis of (-)-apicularen A has been completed. The synthesis features a cyanohydrin acetonide coupling as a convergent approach to the C9-C18 segment and an intramolecular Diels-Alder addition sequence to create both the 10-membered macrocycle and the aromatic ring.

Synthesis of the C1-C28 Portion of Spongistatin 1 (Altohyrtin A)

A synthetic approach was developed to the C1-C28 subunit of spongistatin 1 (altohyrtin A, 65). The key step was the coupling of the AB and CD spiroketal moieties via an anti-aldol reaction of aldehyde 62 and ethyl ketone 57. The development of a method for the construction of the AB spiroketal fragment is described and included the desymmetrization of C2-symmetric diketone 10 and the differentiation of the two primary alcohols of 16. Further elaboration of this advanced intermediate to the desired aldehyde 62 included an Evans' syn-aldol reaction and Tebbe olefination. The synthesis of the CD spiroketal fragment 56 involved the ketalization of a triol-dione, generated in situ by deprotection of 45, to provide a favorable ratio (6-7:1) of spiroketal isomers 46 and 47, respectively. The overall protecting group strategy, involving many selective manipulations of silyl protecting groups, was successfully developed to provide the desired C1-C28 subunit of spongistatin 1 (altohyrtin A) (65).

Enantioselective acyclic stereoselection under catalyst control - III. A very short asymmetric synthesis of the bryostatin C1-C9 segment using the chiral oxazaborolidinone-promoted aldol reaction

A very short asymmetric synthesis of the bryostatin C1-C9 segment was achieved by three sequential chiral oxazaborolidinone-promoted aldol reactions under 'catalyst control'. This synthetic methodology is based on a direct asymmetric

Enantiospecific synthesis of optically pure (3S)-hydroxy esters by the stereocontrolled yeast reduction of α-sulfenyl-β-ketoesters

Stereocontrol in Baker's yeast reduction of β-ketoesters was successfully achieved by introducing the sulfenyl group at the α-position of the esters to afford optically pure (S)-β-hydroxy esters.