20786-73-6

Upstream product

• 1042431-16-2 (3aS,4S,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbaldehyde 
• 3458-28-4 D-Mannose 
• 100-44-7 benzyl chloride 
• 869354-98-3 benzyl 2,3: 5,6-di-O-isopropylidene-D-mannofuranoside 
• 869353-20-8 benzyl 2,3-O-isopropylidene-D-mannofuranoside 

Downstream Products

• 88165-21-3 benzyl 2,3-O-isopropylidene-5-O-trifluoromethylsulphonyl-α-D-lyxofuranoside 
• 92591-96-3 benzyl 5-deoxy-5-iodo-2,3-O-isopropylidene-α-D-lyxofuranoside 
• 92591-95-2 benzyl 2,3-O-isopropylidene-5-O-p-tolylsulphonyl-α-D-lyxofuranoside 
• 88165-22-4 methyl (benzyl 5,6-dideoxy-6-dimethoxyphosphoryl-2,3-O-isopropylidene-α-D-lyxo-heptofuranosid)uronate 
• 92591-97-4 t-butyl (benzyl 5,6-dideoxy-6-dimethoxyphosphoryl-2,3-O-isopropylidene-α-D-lyxo-heptofuranosid)uronate 
• 102854-76-2 (3aS,6R,6aS)-4-Benzyloxy-6-methoxymethoxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole 

Relevant academic research and scientific papers

Fluorous dimethylthiocarbamate (FDMTC) protecting groups for alcohols

N,N-Bis(perfluoroalkyl)thiocarbamoyl chlorides (FDMTC-Cls) were synthesized as reagent for the protection of alcohols. Using the crystalline FDMTC-Cls, the FDMTC groups were introduced into the alcohol molecules in excellent yields in the presence of sodium hydride in THF at room temperature. The products were separated from the excess alcohols by solid-phase extraction with a fluorous reverse-phase silica gel column (Fluorous Solid Phase Extraction; FSPE). The FDMTC groups were readily removed by oxidation with m-chloroperbenzoic acid (m-CPBA) and subsequent hydrolysis with KHCO3.

AN EFFICIENT SYNTHESIS OF (2S,3R)- AND (2S,3S)-SPHINGOSINE

A straightforward sequence of reactions allows the conversion of D(+)-Mannose and D(+)-ribono-1,4-lactone into "erythro"-(2S,3R)- and "threo"-(2S,3S)-sphingosine, respectively.