109715-57-3

Upstream product

• 73679-54-6 (4R,5R)-5-hydroxymethyl-2,2,4-trimethyl-1,3-dioxolane 
• 100-44-7 benzyl chloride 
• 73346-74-4 (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol 
• 37031-29-1 (+)-dimethyl-2,3-O-isopropylidene-D-tartrate 
• 100-39-0 benzyl bromide 
• 109715-58-4 (4R)-3,4-(isopropylidenedioxy)tetrahydrofuran-2-ol 
• 78513-04-9 (4S,5S)-p-toluolsulfonsaeure<(5-benzyloxymethyl-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl)methyl>ester 
• 99666-01-0 (2S,3R)-1-(benzyloxy)-2,3-butanediol 
• 67-64-1 acetone 
• 59779-75-8 diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate 
• 114826-50-5 (4R,5S)-2,2-dimethyl-4-iodomethyl-5-benzyloxymethyl-1,3-dioxolane 
• 37031-29-1 (-)-dimethy-2,3-O-isopropylidene-L-tartrate 
• 78469-77-9 1-O-benzyl-2,3-O-isopropylidene-D-threitol 
• 91526-97-5 (4S,5R)-5-benzyloxymethyl-4-bromomethyl-2,2-dimethyl-1,3-dioxolane 

Downstream Products

• 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 
• 111524-22-2 C₂₇H₄₇NO₅Si 
• 111524-23-3 C₂₇H₄₇NO₅Si 
• 111524-21-1 C₂₄H₄₁NO₅Si 
• 125257-84-3 C₂₄H₄₁NO₅Si 
• 111687-35-5 C₂₄H₄₁NO₅Si 

Relevant academic research and scientific papers

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.

Total synthesis of (+)-colletodiol from (S,S)-tartrate and (R)-3-hydroxybutanoate

The macrodiolide antibiotic (+)-colletodiol (7, Scheme 1) was synthesised.The configuration was thus proven to be (6R,11R,12R,14R). - Key intermediates (Schemes 9 and 10) are the two hydroxy acids 43 and 64, which were prepared from dimethyl (S,S)-tartrate in 20percent overall yield (12 steps) and from (R)-3-hydroxybutanoate in 57percent overall yield (6 steps), respectively.The two hydroxy acids were cyclised to give, after deprotection, the title compound. - Our investigations led to the production of a large number of chiral building blocks, many of them in different stereoisomeric forms.

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).