82043-31-0

Upstream product

• 67470-74-0 (2S,3R,E)-5-phenylpent-4-ene-2,3-diol 
• 77-76-9 2,2-dimethoxy-propane 
• 14371-10-9 (E)-3-phenylpropenal 
• 910792-92-6 (3S,4S,Z)-4-(tert-butyldimethylsiloxy)-1-phenyl-3-(triisopropylsiloxy)-2-(trimethylsilyl)pent-1-ene 

Downstream Products

• 82010-51-3 (4S)-cis-2,2,5-trimethyl-1,3-dioxolane-4-carboxaldehyde 
• 22323-80-4 (4S)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde 
• 85099-89-4 (2S,3R)-4-benzyloxy-2,3-(propane-2,2-dioxy)butane 

Relevant academic research and scientific papers

Synthesis of N-Trifluoroacetyl-L-acosamine and -L-daunosamine

N-Trifluoroacetyl-L-acosamine (18) has been chirally synthesised from the chiral educt (1) obtained from cinnamaldehyde and bakers' yeast, whereas N-trifluoroacetyl-L-daunosamine (17) was obtained by inverting the configuration at C-4 of the intermediate

Highly diastereoselective preparation of anti-1,2-diols by catalytic addition of alkynylsilanes to α-silyloxyaldehydes

The catalytic, diastereoselective coupling of α-silyloxy aldehydes and alkynylsilanes catalyzed by a nickel(0) N-heterocyclic carbene complex provides an effective entry to anti-1,2-diols. The scope of couplings and extent of diastereoselection are excell

Synthesis of Enantiomerically Pure Forms of N-Acyl Derivatives of C-Methyl Analogues of the Aminodeoxy Sugar L-Acosamine from Noncarbohydrate Precursors

The 2S,3R diol 2a and the 3R α-ketol 5b, prepared in fermenting baker's yeast from cinnamaldehyde and α-methylcinnamaldehyde, are converted into the chiral N-trifluoroacetyl deoxy C-methyl-branched amino sugars 15b,c and 19b.Key intermediates in the synthesis are the C4 and C5 chiral aldehydes 9a and 17a and the α,β-unsaturated carbonyl compounds 11a and 18, which upon threo stereoselective addition of ammonia, eventually give 15b,c and 19b.The sterochemistry and the conformations of the aminodeoxy sugar derivatives and of the intermediate lactones are deduced byNMR studies.

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).