11072-19-8

Usage

InChI:InChI=1/C8H14O5/c1-7(11)3-8(4-13-7)6(10)5(9)2-12-8/h5-6,9-11H,2-4H2,1H3/t5-,6+,7?,8?/m1/s1

Upstream product

• 143016-82-4 1,4-anhydro-2,3,5-tri-O-acetyl-4-C-(prop-2-enyl)-L-xylitol 
• 194476-17-0 (3R,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-8-methyl-3-trimethylsilanyloxy-1,7-dioxa-spiro[4.4]nonan-8-ol 
• 33352-06-6 sphydrofuran triacetate 
• 216960-12-2 1,4-anhydro-4-C-(prop-2-enyl)-5-O-triisopropylsilyl-L-xylitol 
• 216960-08-6 1,4-anhydro-2,3-di-O-benzyl-4-C-(prop-2-enyl)-L-xylitol 
• 216960-10-0 1,4-anhydro-2,3-di-O-benzyl-4-C-(prop-2-enyl)-5-O-triisopropylsilyl-L-xylitol 
• 194475-99-5 ((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-furan-3-yl-methanol 
• 184780-79-8 4-[(R)-(tert-Butyl-dimethyl-silanyloxy)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-5H-furan-2-one 
• 194476-01-2 ((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-furan-3-yl-methanone 
• 194476-11-4 4-[(1R,2R)-1-(tert-Butyl-dimethyl-silanyloxy)-2,3-dihydroxy-propyl]-5H-furan-2-one 
• 194476-05-6 tert-Butyl-[(R)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-furan-3-yl-methoxy]-dimethyl-silane 
• 194476-14-7 (3R,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-trimethylsilanyloxy-1,7-dioxa-spiro[4.4]nonan-8-one 
• 194476-08-9 (R)-4-[(R)-(tert-Butyl-dimethyl-silanyloxy)-(5-trimethylsilanyl-furan-3-yl)-methyl]-2,2-dimethyl-[1,3]dioxolane 
• 117774-51-3 (R)-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-furan-3-yl-methanol 

Relevant academic research and scientific papers

Total syntheses of sphydrofuran, secosyrins, and syributins

Two groups of natural products, sphydrofuran (1) and its furan derivative (2) and secosyrins 1 and 2 (3a, 3b) and syributins 1 and 2 (4a, 4b), were synthesized from one precursor (6), which was realized starting from 3-tri-n-butylstannylfuran or 3-bromofuran.

CHEMO-ENZYMATIC SYNTHESIS OF NAATURAL PRODUCTS: SYNTHESIS OF SPHYDROFURAN

A novel synthesis for sphydrofuran 1 has been developed.Starting with achiral materials the chiral centers of the target molecule were introduced via enzymatic methods as well as via a diastereoselective Grignard reaction.Rabbit muscle aldolase (RAMA)-catalyzed aldol condensation of chloroacetaldehyde 3 with dihydroxyacetone phosphate (DHAP) 4 affords the C-5 skeleton of 5 which was transformed to sphydrofuran 1 and its analogue 10 via a Grignard addition of allylmagnesium bromide followed by a Wacker reaction.