85099-89-4

Upstream product

• 78513-04-9 (4S,5S)-p-toluolsulfonsaeure<(5-benzyloxymethyl-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl)methyl>ester 
• 37031-29-1 (-)-dimethy-2,3-O-isopropylidene-L-tartrate 
• 114826-50-5 (4R,5S)-2,2-dimethyl-4-iodomethyl-5-benzyloxymethyl-1,3-dioxolane 
• 50622-09-8 2,3-O-isopropylidene-L-threitol 
• 78469-77-9 (4S,5S)-4-benzyloxymethyl-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolane 
• 59779-75-8 diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate 
• 99666-01-0 (2S,3R)-1-(benzyloxy)-2,3-butanediol 
• 67-64-1 acetone 
• 162932-15-2 (2S,3R,4S,5S)-2,3-(propane-2,2-dioxy)hexane-1,4,5-triol 
• 502481-96-1 (2S,3R)-4-benzyloxy-2,3-(propane-2,2-dioxy)-1-butanol 
• 82043-31-0 (2S,3R) 2,3-isopropylidenedioxy-5-phenylpent-4-ene 
• 73679-52-4 (2R,3S)-2,3-(propane-2,2-dioxy)-1-butanol 
• 100-44-7 benzyl chloride 

Downstream Products

• 85118-86-1 (2R,3S)-1-(Benzyloxy)-2,3-butanediol 
• 85100-00-1 Benzoic acid (1R,2S)-1-benzyloxymethyl-2-hydroxy-propyl ester 
• 85099-93-0 Benzoic acid (1R,2S)-1-benzyloxymethyl-2-(toluene-4-sulfonyloxy)-propyl ester 
• 82010-51-3 (4S)-cis-2,2,5-trimethyl-1,3-dioxolane-4-carboxaldehyde 
• 41167-51-5 (4S,5S)-4-hydroxymethyl-2,2,5-trimethyl-[1,3]-dioxolane 
• 1393793-01-5 tert-butyl (S,S,S)-3-(N-benzyl-N-isopropylamino)-4,5-O-isopropylidene-4,5-dihydroxyhexanoate 
• 1393793-02-6 tert-butyl (3R,4S,5S)-3-(N-benzyl-N-isopropylamino)-4,5-O-isopropylidene-4,5-dihydroxyhexanoate 
• 1393793-05-9 tert-butyl (3S,4S,5S,αR)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5-O-isopropylidene-4,5-dihydroxyhexanoate 
• 1393793-06-0 tert-butyl (3R,4S,5S,αR)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5-O-isopropylidene-4,5-dihydroxyhexanoate 
• 1393793-07-1 tert-butyl (3R,4S,5S,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5-O-isopropylidene-4,5-dihydroxyhexanoate 
• 1393793-08-2 tert-butyl (3R,4S,5S,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5-O-isopropylidene-4,5-dihydroxyhexanoate 
• 73987-14-1 (-)-1-O-p-toluenesulfonyl-4-deoxy-2,3-O-isopropylidene-L-threytol 
• 111524-25-5 C₂₉H₄₃NO₅Si 
• 111524-26-6 C₂₉H₄₃NO₅Si 

Relevant academic research and scientific papers

Versicolactones A and B: Total synthesis and structure revision

To further determine absolute configurations of versicolactones A and B, total synthesis of versicolactones A and B and their six stereoisomers were reported in this Letter. The 1H and 13C NMR spectra of the synthetic erythro-stereoisomers matched perfectly with those of the natural products. Combined with the comparison of the specific rotations, the absolute configuration of versicolactones A and B were revised as (4Z,6R,7S)- and (4E,6R,7S)- from the corresponding (4Z,6R,7R)- and (4E,6R,7R)-6,7-dihydroxyocta- 2,4-dien-4-lactone, respectively.

On the origins of diastereoselectivity in the conjugate additions of the antipodes of lithium N-benzyl-(N-α-methylbenzyl)amide to enantiopure cis- and trans-dioxolane containing α,β-unsaturated esters

"Matching" and "mismatching" effects in the doubly diastereoselective conjugate additions of the antipodes of lithium N-benzyl-(N-α-methylbenzyl)amide to enantiopure cis- and trans-dioxolane containing α,β-unsaturated esters have been investigated. High levels of substrate control were established first upon conjugate addition of achiral lithium N-benzyl-N-isopropylamide to both tert-butyl (S,S,E)-4,5-O- isopropylidene-4,5-dihydroxyhex-2-enoate and tert-butyl (4R,5S,E)-4,5-O- isopropylidene-4,5-dihydroxyhex-2-enoate. However, upon conjugate addition of lithium (R)-N-benzyl-(N-α-methylbenzyl)amide and lithium (S)-N-benzyl-(N-α-methylbenzyl)amide to these substrates, neither reaction pairing reinforced the apparent sense of substrate control. These reactions do not, therefore, conform to the classical doubly diastereoselective "matching" or "mismatching" pattern usually exhibited by this class of reaction. A comparison of these reactions with the previously reported doubly diastereoselective conjugate addition reactions of lithium amide reagents to analogous substrates is also discussed.

THE CHEMISTRY OF SILYLATED KETENE ACETALS: AN EFFICIENT STEREOCONTROLLED SYNTHESIS OF N-BENZOYL L-DAUNOSAMINE

N-Benzoyl L-daunosamine was synthesized with high stereoselectivity utilizing a 1,3-addition of ketene silyl acetal (3a) to the chiral nitrone, (Z)-((4R)-trans-2,2,5-trimethyl-1,3-dioxolan-4-yl)methylene((1S)-1-phenylethyl)amine N-oxide (4c) accompanied by a silyl group-transfer in acetonitrile under mild conditions.

SYNTHESIS OF THE ENANTIOMERIC FORMS OF CIS AND TRANS 1-BENZYLOXY-2,3-EPOXY BUTANE AND OF (3S,4S) 4-METHYL-3-HEPTANOL

The C4 erythro and threo diols (7) and (8) are converted either into the chiral epoxides (13) and (15) or into the enantiomers (14) and (16); the epoxide (13) is used as chiral synthon for the preparation of (3S,4S) 4-methyl-3-heptanol (21).