185155-48-0

Upstream product

• 71998-69-1 (+/-)-4-benzyloxy-butane-1,2-diol 
• 6278-91-7 4-(benzyloxy)-2-butanone 
• 186090-90-4 (+/-)-4-benzyloxy-1-triphenylmethyloxy-2-butanol 
• 94426-71-8 (+/-)-4-(2-benzyloxyethyl)-2,2-dimethyl-1,3-dioxolane 
• 100-39-0 benzyl bromide 
• 186090-91-5 4-benzyloxy-1-triphenylmethyloxy-2-butanone 

Downstream Products

• 115114-87-9 (2R)-2-(2-benzyloxyethyl)oxirane 
• 85960-55-0 (S)-(2-phenylmethoxyethyl)oxirane 
• 132980-13-3 (S)-1-chloro-4-O-benzylbutane-2,4-diol 
• 132980-10-0 (R)-4-Benzyloxy-1-chloro-butan-2-ol 
• 132980-11-1 (S)-4-Benzyloxy-2-chloro-butan-1-ol 
• 132980-14-4 (R)-4-Benzyloxy-2-chloro-butan-1-ol 
• 185155-53-7 (R)-1-Benzyloxy-hexadecan-3-ol 
• 185155-49-1 (S)-(-)-1-benzyloxy-3-hexadecanol 
• 185155-54-8 (R)-(-)-1-benzyloxy-3-hexadecyl acetate 
• 185155-50-4 (S)-(+)-1-benzyloxy-3-hexadecyl acetate 
• 1610616-89-1 4-(2-(benzyloxy)ethyl)-4-vinyl-1,3-dioxolan-2-one 
• 1610617-11-2 (S)-4-(2-(benzyloxy)ethyl)-4-vinyl-1,3-dioxolane 
• 1644060-19-4 C₁₃H₁₈O₃ 
• 1613415-84-1 C₁₁H₁₅NO₅S 

Relevant academic research and scientific papers

Microbial oxidation of 1,2-diols bearing a substituent with an oxyfunctional group: Preparation of optically active 1,2-diols and α-hydroxy ketones

The preparation of optically active 1,2-diols bearing a substituent with a benzyloxy group at the terminus has been achieved by microbial enantioselective oxidation of the racemic compounds. In the screening test, Ochrobactrum sp. MU2293 was selected as the best strain to perform the enantioselective oxidation of (±)-4-benzyloxybutane-1,2-diol to give the corresponding 4-benzyloxy-1-hydroxybutan-2-one and the remaining (R)-diol with a high ee. This microbial oxidation was applicable to other substrates bearing a substituent with a different carbon number. On the other hand, Bacillus sp. MU2289 catalyzed the oxidation of the 1,2-diols to afford the corresponding α-hydroxy ketones and the (S)-diols as the remaining substrates with the opposite absolute configuration.

Synthesis and application of α-D-mannosyl clusters as photoaffinity ligands for mannose-binding proteins: Concanavalin A as a model receptor

Mono-, di-, and tri-antennary α-D-mannopyranosyl derivatives were synthesized as oligosaccharide mimics. The compounds vary in the length of the acyclic aglyconic spacers linking, in the case of the di- and tri-antennary derivatives, the glycosyl endgroup

Synthesis of (S)- and (R)-3-hydroxyhexadecanoic acid

Diol (R)-(+)-3 is prepared either from the hydroxyketone 2 by reduction with fermenting baker's yeast or by hydrolysis of the dioxolane (R)-(+)-1 which is available from dimethyl D-malate as starting material. (R)-(+)-3 could be converted stereoselectively into (R)-(+)-4. Reaction of (+)-4 with dodecylmagnesium bromide yielded the alcohol (S)-(-)-5 with >99% ee. Its acetylation gave (S)-(+)-6 and hydrogenolysis gave the primary alcohol (S)-(+)-7 which could be oxidized selectively to (S)-(+)-8 wih NaIO4/RuCl3. Alkaline hydrolysis of (+)-8 yielded 3-hydroxyhexadecanoic acid (S)-(+)-9 which could be esterified to give the methyl ester (S)-(+)-10 with >99% ee. Starting with the dioxolane (S)-(-)-1, derived from dimethyl L-malate, the 3-hydroxyhexadecanoic acid (R)-(-)-10 could be synthesised via the intemediates (S)-(-)-3, (S)-(-)-4, (R)-(+)-5, (R)-(-)-6, (R)-(-)-7 and (R)-(-)-8. Copyright (C) Elsevier Science Ltd.