680227-31-0

Upstream product

• 14618-80-5 (R)-benzyl glycidol 
• 100-39-0 benzyl bromide 
• 189386-93-4 (2R)-1-benzyloxy-2-hydroxy-5-(trimethylsilyl)-pent-4-yne 
• 994-30-9 triethylsilyl chloride 
• 115352-39-1 (2R)-1-benzyloxy-2-hydroxy-pent-4-yne 
• 1216963-74-4 lithium acetylide-ethylenediamine complex 

Downstream Products

• 680227-33-2 Acetic acid (R)-6-benzyloxy-1-{2-[(2S,3aR,5S,6R,7aR)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxy-6-methyl-hexahydro-furo[3,2-b]pyran-5-yl]-ethyl}-5-triethylsilanyloxy-hex-2-ynyl ester 
• 680227-36-5 Acetic acid (Z)-(R)-6-benzyloxy-1-{2-[(2S,3aR,5R,6R,7aR)-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-methyl-5-methylsulfanyl-hexahydro-furo[3,2-b]pyran-5-yl]-ethyl}-5-triethylsilanyloxy-hex-2-enyl ester 
• 680227-34-3 Acetic acid (Z)-(R)-6-benzyloxy-1-{2-[(2S,3aR,5S,6R,7aR)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxy-6-methyl-hexahydro-furo[3,2-b]pyran-5-yl]-ethyl}-5-triethylsilanyloxy-hex-2-enyl ester 
• 680227-37-6 (Z)-(R)-8-Benzyloxy-1-[(2S,3aR,5R,6R,7aR)-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-methyl-5-methylsulfanyl-hexahydro-furo[3,2-b]pyran-5-yl]-7-triethylsilanyloxy-oct-4-en-3-ol 
• 680227-25-2 (7R)-1-[(1R,3R,4R,6R,8S)-8-tert-butyldiphenylsiloxymethyl-3-methylthio-4-methyl-2,7-dioxabicyclo[4.3.0]non-3-yl](4Z)-7-triethylsiloxy-8-phenylmetoxyoct-4-en-3-one 
• 680227-35-4 Acetic acid (Z)-(R)-6-benzyloxy-1-{2-[(2S,3aR,5R,6R,7aR)-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-methyl-5-methylsulfanyl-hexahydro-furo[3,2-b]pyran-5-yl]-ethyl}-5-hydroxy-hex-2-enyl ester 
• 693251-11-5 (6R)-1-[(1R,3S,4R,7R,9R,11S)-11-tert-butyldiphenylsiloxymethyl-3-methoxy-2,10-dioxa-5-thiatricyclo[7.3.0.0^3,7]dodec-4-yl](3Z)-6-triethylsiloxy-7-phenylmethoxyhept-3-en-2-one 
• 693251-10-4 [(1S,3S,5R,7S,9R,11R,14R,19R)-19-phenylmethoxymethyl-2,4,8,16-tetraoxa-13-thiapentacyclo[14.1.5.0^3,11.0^3,14.0^5,9]icos-19-en-7-yl]tert-butyldiphenylsiloxymethane 
• 693251-09-1 [(2R,11S,12R,14S,15R,17R,19S)-19-tert-butyldiphenylsiloxymethyl-15-methyl-13,18-dioxadispiro(2H-3,6-dihydropyran-6,5'-oxolane-2',3''-bicyclo[4.3.0]nonane)-2-yl]phenylmethoxymethane 
• 680227-32-1 (R)-8-Benzyloxy-1-[(2S,3aR,5S,6R,7aR)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxy-6-methyl-hexahydro-furo[3,2-b]pyran-5-yl]-7-triethylsilanyloxy-oct-4-yn-3-ol 

Relevant academic research and scientific papers

Chemical variation of natural product-like scaffolds: Design and synthesis of spiroketal derivatives

The design and synthesis of spiroketal structures and their chemical modification, leading to a collection of new small molecules for biological evaluation as orally-bioavailable lead compounds is described. Both [6,5]- and [6,6]-membered ring spiroketal units have been prepared in a stereochemically-varying fashion starting from commercially available (R)- or (S)-glycidol, in ten, eleven and twelve linear steps, in overall yields of 45, 40 and 20%, respectively. Further elaboration according to Lipinski's guidelines has given a collection of structurally-diverse, new spiroketal derivatives in high yields and with high purity. The Royal Society of Chemistry 2006.

Double conjugate addition of dithiols to propargylic carbonyl systems to generate protected 1,3-dicarbonyl compounds

The work describes the efficient double conjugate addition of ethane and propane dithiols in the presence of sodium methoxide to a wide variety of propargylic carbonyl containing compounds. The products of these reactions are differentiated, 1,3-dicarbony

Synthetic studies on azaspiracid, a novel shellfish poison: Attempts to construct the ABCD ring system

Synthesis of the ABCD ring system of azaspiracid (1) was attempted. Construction of the highly substituted tetrahydrofuran (9) via the Pd(0)-mediated cyclization, followed by spirocyclization afforded trispiro-ring (28), carrying an unnatural ring-junctions. The BCD ring system of I was successfully produced by using the bridge of a sulfur atom between the B and C ring to control the spiroacetal center of the C13 position. The stereostructures were unambiguously determined by the NOE experiments.