328383-01-3

Upstream product

• 2873-29-2 D-glucal triacetate 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 328383-00-2 2-(tert-butyl-diphenyl-silanyloxymethyl)-6-propa-1,2-dienyl-3,6-dihydro-2H-pyran-3-ol 
• 328382-98-5 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside propadiene 
• 328382-99-6 (2R,3S,6S)-2-Hydroxymethyl-6-propa-1,2-dienyl-3,6-dihydro-2H-pyran-3-ol 

Downstream Products

• 328382-96-3 (2R,5S,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-(dimethyl-phenyl-silanyl)-6-propa-1,2-dienyl-dihydro-pyran-3-one 
• 328382-94-1 2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(dimethyl-phenyl-silanyl)-4-{hydroxy-[3,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-methyl}-6-propa-1,2-dienyl-dihydro-pyran-3-one 

Relevant academic research and scientific papers

Synthesis of a (2R,6R)-2-(hydroxymethyl)-6-propa-1,2-dienyl-2H-pyran-3(6H)-one derivative, a new enone for the convergent construction of C-glycosides of C-disaccharides

The previously unknown (2R,6R)-2[(tert-butyl)diphenylsilyloxy]-6-propa-1,2-dienyl-2H-pyran-3(6H)-one (16) was derived from tri-O-acetylglucal. Conjugate addition of PhSAlMe2 to 16 followed by enolate trapping with 1,2-O-isopropylidene-3-O-methyl-α-D-xylo-pentodialdo-1,4-furanose and NaBH4 reduction of the intermediate aldol furnished a new C-glycoside of a C-disaccharide: 4,8-anhydro-9-O-[(tert-butyl)diphenylsilyl]-6-[(5R)-1,2-O-isopropylidene-3-O- methyl-α-D-xylo-furanos-5-C-yl]-5-S-phenyl-1,2,3,6-tetradeoxy-5-thio-D- glycero-L-gulo-nona-1,2-dienitol (24). Similarly, conjugate addition of PhMe2SiZnMe2Li to 16, followed by cross-aldol reaction with 2,6-anhydro-1,3,4,5-tetra-O-[(tert-butyl)dimethylsilyl]-D-glycero-L-manno-hep tose (27), and reduction gave either 4,8-anhydro-6-{(1S)-2,6-anhydro-3,4,5,7-tetra-O-[(tert-butyl)dimethylsilyl-D- glycero-L-manno-heptitol-1-C-yl}-9-O-[tert-butyl)diphenylsilyl]-1,2,3,5,6-pen tadeoxy-5-phenyldimethylsilyl-D-glycero-D-manno-(29) or L-gulo-nona-1,2-dienitol (30).