214678-61-2

Basic information

• Product Name: (R)-4-Benzenesulfonyl-6-((1R,2S)-1,2-dihydroxy-2-phenyl-ethyl)-tetrahydro-pyran-2-one
• Synonyms: (R)-4-Benzenesulfonyl-6-((1R,2S)-1,2-dihydroxy-2-phenyl-ethyl)-tetrahydro-pyran-2-one
• CAS NO: 214678-61-2
• Molecular Weight: 376.43
• Mol File: 214678-61-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (R)-4-Benzenesulfonyl-6-((1R,2S)-1,2-dihydroxy-2-phenyl-ethyl)-tetrahydro-pyran-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-4-Benzenesulfonyl-6-((1R,2S)-1,2-dihydroxy-2-phenyl-ethyl)-tetrahydro-pyran-2-one(214678-61-2)
• EPA Substance Registry System: (R)-4-Benzenesulfonyl-6-((1R,2S)-1,2-dihydroxy-2-phenyl-ethyl)-tetrahydro-pyran-2-one(214678-61-2)

Safety Data

• Hazardous Substances Data: 214678-61-2(Hazardous Substances Data)

Upstream product

• 214678-60-1 3-Benzenesulfonyl-4-{(4R,5S)-5-[(S)-(tert-butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-butyric acid methyl ester 
• 179618-34-9 ethyl (2S,3S,4R)-4-{[(tert-butyl)(dimethyl)silyl]oxy}-2,3-dihydroxy-4-phenylbutanoate 
• 179618-33-8 ethyl (2E,4S)-4-{[(tert-butyl)(dimethyl)silyl]oxy}-4-phenylbut-2-enoate 
• 187931-99-3 ethyl (4S,5S)-5-[(R)-{[(tert-butyl)(dimethyl)silyl]oxy}(phenyl)methyl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate 
• 252273-55-5 ethyl (2S,3R,4S)-2,3-isopropylidenedioxy-4-(4-nitrobenzyloxy)-4-phenylbutanoate 
• 252273-57-7 ethyl (2S,3R,4S)-4-(t-butyldiphenylsilyloxy)-2,3-isopropylidenedioxy-4-phenylbutanoate 
• 252273-54-4 ethyl (2S,3R,4R)-4-hydroxy-2,3-isopropylidenedioxy-4-phenylbutanoate 
• 252273-56-6 ethyl (2S,3R,4S)-4-hydroxy-2,3-isopropylidenedioxy-4-phenylbutanoate 
• 252273-61-3 (1S,2S,3R)-1-(t-butyldiphenylsilyloxy)-2,3-isopropylidenedioxy-1-phenylbutan-4-ol 
• 252273-62-4 (2R,3S,4S)-1-(t-butyldiphenylsilyloxy)-2,3-isopropylidenedioxy-4-phenyl-1-trifluoromethanesulfonyloxybutane 
• 214678-58-7 (4R)-4-t-butyldimethylsilyloxy-4-phenyl-2S,3S-O-isopropylidene-butanol 
• 214678-59-8 Trifluoro-methanesulfonic acid (4R,5S)-5-[(S)-(tert-butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester 

Downstream Products

• 136685-37-5 (1R,5R,7S,8S)-8-hydroxy-7-phenyl-2,6-dioxa-bicyclo-[3.3.1]-nonan-3-one 

Relevant articles and documents

Total synthesis of antitumor Goniothalamus styryllactones

Synthesis of eight enantiopure styryllactones has been achieved from a common precursor: ethyl (2S, 3S, 4R)-4-(t-butyldimethylsilyloxy)-2,3- isopropylidenedioxy-4-phenylbutanoate 16, prepared in five steps and 65% yield from (R)-mandelic acid. Key elements for the synthesis of goniofufurone 3, goniopypyrone 4, goniobutenolides A and B (5, 6) and 7-epi-goniofufurone 7 were the introduction of the Z-acrylate moiety by a Julia coupling between 16 or its epimer in benzylic position and methyl 3-phenylsulfonyl orthopropionate 11 followed by a highly diastereoselective reduction of the resulting β-keto sulfone which sets up the last of the four contiguous asymmetric center. In the case of styryllactones 4 and 7, prior to the Julia coupling, the benzyl sterocenter of 16 was efficiently inverted by a Mitsunobu reaction. Goniodiol 1 and 9-deoxygoniopypyrone 2 were synthesized via an efficient coupling between the primary triflate derived from the common intermediate 16 or its epimer and Ghosez's sulfone 11 followed by lactonization and PhSO2H elimination. Goniodiol 1 has been efficiently converted to another styryllactone: isogoniothalamin epoxide 41. Addition of the Ghosez's sulfone to an epoxide derived from the enantiomer of 16 allowed a short synthesis of 8-epi-9-deoxygoniopypyrone 8, thereby establishing that its structure is the following: (1R, 5R, 7S, 8S)-8-hydroxy-7-phenyl-2,6- dioxabicyclo[3.3.1] nonan-3-one.