ChemInform Abstract: Chemical Synthesis of 1‐Deoxy‐L‐Fructose and L‐Sorbose Through Carbonyl Translocation.

Wu, Hsin‐Pei; Hsu, Nai Yun; Lu, Tai‐Ni; Chang, Che-Chien

doi:10.1002/chin.201522241

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Chemical Synthesis Of 2-l-ketohexoses1

By Isomerization/conversion Of An Aldohexose1

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2015

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“…Oxidation of the 5-OH to a ketone followed by removal of the trityl group gave 454 , which could be hydrogenolyzed to l -sorbose (Scheme ) . Recently, this synthesis was repeated claiming slightly higher yields …”

Section: Chemical Synthesis Of 2-l-ketohexosesmentioning

confidence: 99%

“…318 Recently, this synthesis was repeated claiming slightly higher yields. 319 L-Tagatose (31) has been made from 1,5-anhydro-D-galactitol (468, Scheme 67), which itself can be readily made from Dgalactose (30). Reaction of 468 with dimethoxypropane and acid gave a 1:1 mixture of the 3,4-O-isopropylidene-2,6-di-Omethoxypropyl derivative and the 3,4-O-isopropylidene-2,6-di-O-methoxypropyl derivative which upon mild hydrolysis and benzylation gave 469 (Scheme 67).…”

Section: By Isomerization/conversion Of An Aldohexosementioning

confidence: 99%

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