109715-57-3

Basic information

• Product Name: (R,R)-4-benzyloxymethyl-2,2,5-trimethyl-1,3-dioxolane
• Synonyms: (R,R)-4-benzyloxymethyl-2,2,5-trimethyl-1,3-dioxolane
• CAS NO: 109715-57-3
• Molecular Weight: 236.311
• Mol File: 109715-57-3.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (R,R)-4-benzyloxymethyl-2,2,5-trimethyl-1,3-dioxolane(CAS DataBase Reference)
• NIST Chemistry Reference: (R,R)-4-benzyloxymethyl-2,2,5-trimethyl-1,3-dioxolane(109715-57-3)
• EPA Substance Registry System: (R,R)-4-benzyloxymethyl-2,2,5-trimethyl-1,3-dioxolane(109715-57-3)

Safety Data

• Hazardous Substances Data: 109715-57-3(Hazardous Substances Data)

Upstream product

• 73679-54-6 (4R,5R)-5-hydroxymethyl-2,2,4-trimethyl-1,3-dioxolane 
• 100-44-7 benzyl chloride 
• 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 
• 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 
• 78513-04-9 (4S,5S)-p-toluolsulfonsaeure<(5-benzyloxymethyl-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl)methyl>ester 
• 109715-58-4 (4R)-3,4-(isopropylidenedioxy)tetrahydrofuran-2-ol 
• 78469-77-9 1-O-benzyl-2,3-O-isopropylidene-D-threitol 
• 100-39-0 benzyl bromide 
• 37031-29-1 (+)-dimethyl-2,3-O-isopropylidene-D-tartrate 

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 
• 111524-21-1 methyl (4S,5S)-3--4,5-(isopropylidenedioxy)hexanoate 
• 111524-25-5 methyl (4S,5S)-3--4,5-(isopropylidenedioxy)hexanoate 
• 111524-22-2 tert-butyl (4S,5S)-3--4,5-(isopropylidenedioxy)hexanoate 
• 111524-19-7 tert-butyl (4S,5S)-3--4,5-(isopropylidenedioxy)hexanoate 
• 111524-17-5 methyl (4S,5S)--4,5-(isopropylidenedioxy)hexanoate 
• 111524-24-4 methyl (3S,4S,5S)-3--4,5-(isopropylidenedioxy)hexanoate 
• 111612-93-2 (Z)-((4R)-trans-2,2,5-trimethyl-1,3-dioxolan-4-yl)methylene((1S)-1-phenylethyl)amino N-oxide 

Relevant articles and documents

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.

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.

Practical enantiospecific syntheses of (±) erythro-9-(2S-hydroxy-3R-nonyl) adenine

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