Sciencemadness Discussion Board

Wolfroms synthesis fructose

jecazmaj - 22-8-2007 at 07:33

Wolfroms synthesis fructose from image attached ... This is my exam question. Anyone ?

New Bitmap Image.GIF - 2kB

Nicodem - 22-8-2007 at 12:56

Quote:
Originally posted by jecazmaj
Wolfroms synthesis fructose from image attached ...

How can you synthesize fructose from an image? If this Wolfroms really synthesized anything from an image, attached or not, he must have been a real genius!

JohnWW - 22-8-2007 at 14:30

If that is supposed to be fructose tetra-acetate, it can be converted back to fructose by hydrolysis with an aqueous mineral acid..

Ozone - 22-8-2007 at 15:30

Actually, the synthesis if from ababinonic acid and is rather interesting (why, when fructose is so cheap?).

From the patent:
United States Patent 4623721

Synthesis of L-fructose and derivatives thereof
by:

Chen, Chyi-Cheng (Gaithersburg, MD, US)
Whistler, Roy L. (West Lafayette, IN, US):


L-Fructose, which has not been found in nature, was synthesized for the first time by Fischer. See E. Fischer, Ber., 23 (1890) 370-394. DL-Glucose phenylosazone was prepared from .alpha.-acrose and hydrolyzed to the glycosulose, which was reduced to DL-fructose. L-Fructose was isolated from the mixture. L-Fructose was later synthesized by Wolfrom and Thompson from L-arabinonic acid in five steps. See M. L. Wolfrom and A. Thompson, Methods of Carbohydr. Chem., 1 (1962) 118-120.

Cheers,

O3

jecazmaj - 23-8-2007 at 01:00

Quote:
Originalno postavio/la Nicodem
Quote:
Originally posted by jecazmaj
Wolfroms synthesis fructose from image attached ...

How can you synthesize fructose from an image? If this Wolfroms really synthesized anything from an image, attached or not, he must have been a real genius!


You are so funny ...

jecazmaj - 23-8-2007 at 01:05

Quote:
Originalno postavio/la Ozone
Actually, the synthesis if from ababinonic acid and is rather interesting (why, when fructose is so cheap?).

From the patent:
United States Patent 4623721

Synthesis of L-fructose and derivatives thereof
by:

Chen, Chyi-Cheng (Gaithersburg, MD, US)
Whistler, Roy L. (West Lafayette, IN, US):


L-Fructose, which has not been found in nature, was synthesized for the first time by Fischer. See E. Fischer, Ber., 23 (1890) 370-394. DL-Glucose phenylosazone was prepared from .alpha.-acrose and hydrolyzed to the glycosulose, which was reduced to DL-fructose. L-Fructose was isolated from the mixture. L-Fructose was later synthesized by Wolfrom and Thompson from L-arabinonic acid in five steps. See M. L. Wolfrom and A. Thompson, Methods of Carbohydr. Chem., 1 (1962) 118-120.

Cheers,

O3


thanks