83458-88-2

Upstream product

• 100-39-0 benzyl bromide 
• 184343-54-2 C₁₅H₂₆O₄ 
• 184343-56-4 4,5-Bis-(tetrahydro-pyran-2-yloxy)-pentan-1-ol 
• 6318-30-5 2,2-dimethyl-4-(3-hydroxypropyl)-1,3-dioxolane 
• 821-09-0 n-Pent-4-enyl alcohol 
• 81518-74-3 1-benzyloxy-4-pentene 
• 100-44-7 benzyl chloride 
• 4568-67-6 (+/-)-5-benzyloxy-1,2-isopropylidenedioxypentane 
• 87205-38-7 (+/-)-(2R,3R)-5-benzyloxy-2,3-epoxy-1-pentanol 
• 85531-70-0 [3-(2-Benzyloxy-ethyl)-oxiranyl]-methanol 

Downstream Products

• 171110-95-5 4-<3-(benzyloxy)propyl>-1,3-dioxolan-2-one 
• 575452-49-2 7-(benzyloxy)-4-hydroxyhept-1-ene 
• 186090-98-2 5-benzyloxy-1-hydroxypentan-2-one 
• 171335-60-7 (2S)-5-O-benzylpentane-1,2,5-triol 
• 186091-00-9 2-azi-5-benzyloxy-1-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyloxy)pentane 
• 186091-02-1 2-azi-1-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyloxy)-6-oxa-8-thianonane 
• 186091-01-0 2-azi-1-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyloxy)-5-pentanol 
• 186090-97-1 5-benzyloxy-1-triphenylmethyloxy-2-pentanone 
• 186090-99-3 [3-(3-Benzyloxy-propyl)-3H-diazirin-3-yl]-methanol 
• 186090-96-0 (+/-)-5-benzyloxy-1-triphenylmethyloxy-2-pentanol 
• 5470-84-8 4-benzyloxybutanal 

Relevant academic research and scientific papers

Synthesis of Novel C-Pivot Lariat 18-Crown-6 Ethers and Their Efficient Purification

The syntheses of various lariat ethers including several not previously reported and their efficient purification are presented. The synthesis route brings together reactions from a variety of previous works leading to a robust and generalized approach to these C-pivot lariats. The main steps are condensation of functionalized diols with pentaethylene glycol ditosylate in the presence of potassium as a templating cation. Purification of the final products was achieved without chromatography by extracting from an aqueous potassium hydroxide solution.

Lewis acid-promoted addition of 1,3-bis(silyl)propenes to aldehydes: A route to 1,3-dienes

The Lewis acid-promoted addition of 1,3-bis(silyl)-propenes to aldehydes to provide the corresponding (E)-1,3-dienes in excellent stereoselectivity and good to excellent yields is reported. The procedure is mild, base-free, and operationally straightforward.

Lipase TL-mediated kinetic resolution of 5-benzyloxy-1-tert-butyldimethylsilyloxy-2-pentanol at low temperature: Concise asymmetric synthesis of both enantiomers of a piperazic acid derivative

Lipase TL-mediated kinetic resolution of (± )-5-benzyloxy-1-tert-butyldimethylsilyloxy-2-pentanol (5) at low temperature proceeded to give the corresponding (S)-alcohol 5 and (R)-acetate 6 in quantitative yields with high enantiomeric purity. The addition of bases such as pyridine, DMAP, 2,4- and 2,6-lutidines, or triethylamine considerably enhanced the rate of kinetic resolution. The alcohol (S)-5 and the acetate (R) -6 were converted to piperazic acid derivatives (R)- and (S)-3, respectively, via the intramolecular Mitsunobu reaction as a key step.

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

Preparation of optically active diol derivatives by the enzymatic hydrolysis of cyclic carbonates

A simple enzymatic method for the preparation of optically active 1,2- and 1,3-diol derivatives is disclosed. In the screening of enzymes, racemic 4-[(2-benzyloxy)ethyl]-1,3-dioxolan-2-one (1a) was enantioselectively hydrolyzed by porcine pancreas lipase (PPL) to give optically active (R)-1a and (S)-4-(benzyloxy)butane-1,2-diol (2a). The addition of 10% i-PT2O to the reaction system dramatically improved the reactivity to afford optically pure (A)-1a in 31% yield. PPL also catalyzed the hydrolysis of several five-membered cyclic carbonates with high enatioselectivity. It is noteworthy that the increment of the carbon number of the substituents reflects the drastic increase in enantioselectivity. On the other hand, the hydrolyses of six- and seven-membered cyclic carbonates were also catalyzed by PPL. In particular, the reaction of a six-membered substrate enantioselectively proceeded. This reaction afforded optically active 1,3-diol derivatives which could not be directly prepared by hitherto known methods using hydrolytic enzymes.

REDUCTIVE RING OPENINGS OF ALLYL-ALCOHOL EPOXIDES

Red-Al reduction of allyl-alcohol epoxides was shown to yield 1,3-diols in high regioselectivity, while DIBAL reduction was shown to yield 1,2-diols.

REGIOSELECTIVE REDUCTIONS OF 2,3-EPOXY ALCOHOLS

Regioselective reduction of 3-substituted-2,3-epoxy alcohols to 1,3-diols with sodium bis(2-methoxyethoxy)aluminum hydride (Red-al) is shown to be a general reaction for these substrates.