Title of article :
Synthesis of 6-deoxy-5-thio-d-glucose
Author/Authors :
Eva Boz?، نويسنده , , S?ndor Boros، نويسنده , , J?nos Kuszmann، نويسنده , , Eszter Gacs-Baitz، نويسنده ,
Issue Information :
دوهفته نامه با شماره پیاپی سال 1996
Pages :
15
From page :
159
To page :
173
Abstract :
Three routes were investigated for the conversion of d-glucose into the title compound. In the first approach, reduction of the 5,6-thürane ring of 5,6-dideoxy-5,6-epithio-1,2-O-isopropylidene α-d-glucofuranose (17) as well as that of its 3-O-allyl derivative (13) with lithium aluminium hydride was investigated; 17 afforded the corresponding 6-deoxy derivative besides di-, tri-, and poly-mers, whereas only polymers were formed from 13. In the second approach, the oxirane ring of 3-O-allyl-5,6-anhydro-1,2-O-isopropylidene-β-l-idofuranose was reduced by sodium borohydride and the resulting 6-deoxy derivative was converted into the 5-thiobenzoate; the corresponding hex-4-enofuranose was formed as a byproduct. In the third approach partial mesylation of methyl 5-thio-α-d-glucopyranoside was attempted, but the 6-mesylate 27 could be isolated only in modest yield (28%) together with rearranged 2,5-thioanhydromannofuranoside derivatives. The mechanism of this rearrangement is discussed in detail. The 6-mesylate 27 was converted via the 6-iodo derivative into the title compound.
Keywords :
6-thiirane rings with LiAIH4 , Reaction mechanism , Rearrangement reactions of mesylated methyl 5-thio-?-d-glucopyranoside , transannular participation of the sulfur atom , Reduction of 5 , 6-Deoxy-5-thio-d-glucose
Journal title :
Carbohydrate Research
Serial Year :
1996
Journal title :
Carbohydrate Research
Record number :
961525
Link To Document :
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