110455-86-2

Upstream product

• 81445-44-5 (S)-2-(benzyloxy)propanal 
• 81555-24-0 (E)-but-2-enyl N,N-diisopropylcarbamate 
• 54783-72-1 ethyl (S)-2-(benzyloxy)propionate 

Downstream Products

• 161925-52-6 (3S,4R,5S)-5-benzyloxy-1-(N,N-diisopropylcarbamoyloxy)-3-methyl-4-phenylthiohex-1-ene 
• 121408-82-0 Diisopropyl-carbamic acid (2S,3R,4S,5S)-5-((S)-1-benzyloxy-ethyl)-3-hydroxy-4-methyl-tetrahydro-furan-2-yl ester 
• 121408-87-5 5-O-Benzyl-3,6-dideoxy-3-C-methyl-α-L-talofuranose 
• 121408-88-6 5-O-Benzyl-3,6-dideoxy-3-C-methyl-β-L-talofuranose 
• 110418-34-3 Methyl 5-O-benzyl-3,6-dideoxy-3-C-methyl-β-L-talofuranoside 
• 161925-51-5 (3S,4R,5S)-5-benzyloxy-1-(N,N-diisopropylcarbamoyloxy)-4-methanesulfonyloxy-3-methylhex-1-ene 
• 110418-32-1 (1S,2R,3S,4S,5S)-5-Benzyloxy-1,2-epoxy-4-hydroxy-3-methylhexyl N,N-diisopropylcarbamate 

Relevant academic research and scientific papers

Enantiomerically Pure 2-(Carbamoyloxy)oxiranes and Their Utility in the Synthesis od D- and L-3,6-Dideoxy-3-C-methylhexofuranosides via the Homoaldol Reaction

As an example of a novel flexible strategy in the rapid enantioselective construction of branched carbohydrate analogues by the homoaldol reaction, the title compounds were synthesized. α-Metalated (E)-2-butenyl N,N-diisopropylcarbamate is added to (S)- or (R)-2-benzyloxypropanal.The homoaldol adducts are epoxidized; methanolysis affords furanosides of branched 3,6-dideoxyaldohexoses, or, hydrolysis yields the furanoses.

Sparteine complexes of lithiated primary O-2-alkenyl carbamates stereochemistry of the lithium-titanium exchange and application for the synthesis of enantiomerically enriched γ-lactones

The preferentially formed (-)-sparteine complex from 1-lithio-2-butenyl N,N-diisopropylcarbamate has (S)-configuration at the metal bearing carbon atom, in contrary to our previous assumption. Transmetallation with titanium tetraisopropoxide and the carboxylation proceed with inversion. The addition of aldehydes occurs in an anti-S(E)'-process. The enantioselective synthesis of homoaldol adducts and some corresponding γ-lactones is reported.