195321-30-3

Basic information

• Product Name: [(R)-2-((S)-Benzo[1,3]dioxol-5-yl-methoxymethoxy-methyl)-pent-4-enyloxy]-tert-butyl-diphenyl-silane
• Synonyms: [(R)-2-((S)-Benzo[1,3]dioxol-5-yl-methoxymethoxy-methyl)-pent-4-enyloxy]-tert-butyl-diphenyl-silane
• CAS NO: 195321-30-3
• Molecular Weight: 518.725
• Mol File: 195321-30-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: [(R)-2-((S)-Benzo[1,3]dioxol-5-yl-methoxymethoxy-methyl)-pent-4-enyloxy]-tert-butyl-diphenyl-silane(CAS DataBase Reference)
• NIST Chemistry Reference: [(R)-2-((S)-Benzo[1,3]dioxol-5-yl-methoxymethoxy-methyl)-pent-4-enyloxy]-tert-butyl-diphenyl-silane(195321-30-3)
• EPA Substance Registry System: [(R)-2-((S)-Benzo[1,3]dioxol-5-yl-methoxymethoxy-methyl)-pent-4-enyloxy]-tert-butyl-diphenyl-silane(195321-30-3)

Safety Data

• Hazardous Substances Data: 195321-30-3(Hazardous Substances Data)

Upstream product

• 195321-27-8 (S)-3-[(S)-2-((S)-Benzo[1,3]dioxol-5-yl-hydroxy-methyl)-pent-4-enoyl]-4-benzyl-oxazolidin-2-one 
• 195321-26-7 (1S,2R)-2-allyl-1-(3,4-methylenedioxyphenyl)-1,3-propanediol 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 104266-88-8 (4S)-4-benzyl-3-pent-4-enoyl-1,3-oxazolidin-2-one 
• 120-57-0 piperonal 
• 107-30-2 chloromethyl methyl ether 
• 195321-29-0 (1S,2R)-1-Benzo[1,3]dioxol-5-yl-2-(tert-butyl-diphenyl-silanyloxymethyl)-pent-4-en-1-ol 

Downstream Products

• 157207-93-7 sesaminone 
• 195321-38-1 C₄₃H₅₄O₈Si₂ 
• 195321-37-0 (3R,4S)-1,4-Bis-benzo[1,3]dioxol-5-yl-3-(tert-butyl-diphenyl-silanyloxymethyl)-4-methoxymethoxy-butan-1-ol 
• 195321-31-4 (3R,4S)-1,4-Bis-benzo[1,3]dioxol-5-yl-3-(tert-butyl-diphenyl-silanyloxymethyl)-4-methoxymethoxy-butan-1-one 
• 195321-33-6 Benzo[1,3]dioxol-5-yl-[(3S,4R,5S)-5-benzo[1,3]dioxol-5-yl-4-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl]-methanone 
• 195321-36-9 (3R,4S)-4-Benzo[1,3]dioxol-5-yl-3-(tert-butyl-diphenyl-silanyloxymethyl)-4-methoxymethoxy-butyraldehyde 
• 195321-35-8 (4R,5S)-5-Benzo[1,3]dioxol-5-yl-4-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxymethoxy-pentane-1,2-diol 

Relevant articles and documents

Asymmetric synthesis of sesaminone: Confirmation of its structure and determination of its absolute configuration

An asymmetric synthesis of the naturally occurring antipode of the tetrahydrofuran lignan sesaminone ((-)-1) has been achieved. An X-ray crystal structure of the synthetic material validated the structure proposed in the literature for this lignan. Additionally, the absolute configuration of the natural product was established by correlation of the synthetic tetrahydrofuran with the known absolute configuration of L-Phe. The opening of the synthesis was a diastereoselective Evans aldol reaction between N-4- pentenoyloxazolidinone 6 and piperonal. Reduction of the major diastereomer of the aldol product provided enantiomerically pure diol 4. The primary and secondary hydroxyl groups of 4 were protected in tandem to generate silyl ether-MOM ether 9. The vinyl group contained in 9 was then elaborated, via a series of four steps, to aryl ketone 10. This aryl ketone was transformed to a mixture of silyl enol ether stereoisomers (11a,b); TiCl4-mediated activation of the MOM ethers contained in this mixture of enol ethers yielded tetrahydrofuran 12 as the major product. Treatment of 12 with fluoride provided synthetic (-)-1.