158649-25-3

Upstream product

• 606942-41-0 (4S)-tert-butyl-[3-(2,2-dimethyl-1,3-dioxolan-4-yl)propoxy]diphenylsilane 
• 19131-21-6 (2S)-pentane-1,2,5-triol 
• 51268-87-2 (4S)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)propan-1-ol 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 1358918-30-5 tert-butyl (3-(oxiran-2-yl)propoxy)diphenylsilane 

Downstream Products

• 471261-23-1 (2S)-toluene-4-sulfonic acid 5-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-pentyl ester 
• 106731-75-3 (2S)-5-(tert-butyldiphenylsilyloxy)-1,2-epoxypentane 
• 606942-43-2 (S)-7-((tert-butyldiphenylsilyl)oxy)hept-1-yn-4-ol 
• 606942-42-1 (4S)-7-(tert-butyldiphenylsilyloxy)-1-trimethylsilylhept-1-yn-4-ol 
• 606942-40-9 (4S)-4-benzyloxy-7-(tert-butyldiphenylsilyloxy)hept-1-yne 
• 188442-93-5 (S)-1-benzyloxy-5-bromopentan-2-ol 
• 188443-03-0 ((2R,6S)-6-Benzyloxymethyl-tetrahydro-pyran-2-yl)-acetic acid methyl ester 
• 188442-87-7 (S)-1-benzyloxy-2-tetrahydropyranyloxypentan-5-ol 
• 188442-98-0 (E)-3-((S)-1-Benzyloxymethyl-4-bromo-butoxy)-acrylic acid methyl ester 
• 188442-90-2 [(S)-5-Benzyloxy-4-(tetrahydro-pyran-2-yloxy)-pentyloxy]-tert-butyl-diphenyl-silane 
• 127793-68-4 (S)-1-(tert-butyldiphenylsiloxy)-4-hydroxyhept-6-ene 
• 169304-50-1 (R)-1-(tert-butyldiphenylsilyloxy)-7-octen-4-ol 
• 169304-52-3 (S)-3-(1-tert-Butyldiphenylsilyloxyoct-7-en-4-yl)-2,3-dihydrooxazol-2-one 
• 169304-51-2 (S)-3-(1-tert-Butyldiphenylsilyloxyoct-7-en-4-yl)oxazolidine-2,4-dione 

Relevant academic research and scientific papers

Halocarbocyclization entry into the oxabicyclo[4.3.1]decyl exomethylene-δ-lactone cores of linearifolin and zaluzanin A: Exploiting combinatorial catalysis

A streamlined entry into the sesquiterpene lactone (SQL) cores of linearifolin and zaluzanin A is described. Stereochemistry is controlled through transformations uncovered by ISES (In Situ Enzymatic Screening). Absolute stereochemistry derives from kinet

Stereoselective total synthesis of (-)-aspinolide B from (R)-2,3-O-isopropylideneglyceraldehyde

A stereoselective total synthesis of (-)-aspinolide B by a convergent strategy is reported. Georg Thieme Verlag Stuttgart.

Synthesis of the spiroacetal fragment of broussonetine H

(2S,6S)-2-(3-Bromopropyl)-1,7-dioxaspiro[5.5]undecane 3 was prepared by the addition of the acetylide derived from (4S)-4-benzyloxy-7-tert-butyldiphenylsilyloxyhep-1-yne 8 to δ-valerolactone 6 followed by treatment with hydrogen and palladium on charcoal which effected hydrogenation of the alkyne, hydrogenolysis of the benzyl ether and subsequent spiroacetal formation. The (4S)-stereochemistry in acetylene 8 was established by addition of trimethylsilylacetylene 10 to (2S)-epoxide 9, which in turn is derived from L-glutamic acid 11.

Diastereoselective synthesis of 2,5-disubstituted 3-hydroxypyrrolidine and 2,6-disubstituted 3-hydroxypiperidine derivatives by radical cyclisation; synthesis of (+)-bulgecinine and (-)-desoxoprosopinine

Cyclisation of the O-stannyl ketyl, generated from the aldehyde 17 by reaction with tributyltin hydride in the presence of AIBN, gives the 5-benzyloxymethyl-7-hydroxypyrrolooxazolidin-2-ones as a diastereoisomeric mixture of 7α-ol 18 and 7β-ol 19 (2:1), with high diastereoselectivity with respect to the 5,7a positions. (+)-Bulgecinine 8 is enantioselectively synthesised by stereospecific reduction of the ketone 20, derived from compounds 18 and 19. In a similar way, cyclisation of compound 40 gives a 2:1 mixture of compounds 41 and 42. Conversion of compound 41 into (-)-desoxoprosopinine 9 is successfully achieved.

Enantioselective synthesis of (-)-desoxoprosopinine by radical cyclization

Reaction of the aldehyde 12 with tributyrin hydride in the presence of AIBN gave a mixture of 13 as a 2:1 mixture of 8β-ol and 8α-ol. Conversion of 14, derived from 13, to (-)-desoxoprosopinine 3 was successfully achieved.