TY - JOUR
T1 - De novo highly stereocontrolled synthesis of 2,6-dideoxy sugars by use of 2,6-anhydro-2-thio sugars
AU - Toshima, Kazunobu
AU - Yoshida, Takehito
AU - Mukaiyama, Satsuki
AU - Tatsuta, Kuniaki
N1 - Funding Information:
We are grateful to the Institute of Microbial Chemistry for the generouss upport of our program. Financial support by the Ministry of Education, Sciencea nd Culture (Grant-in-Aid for Scientific Research)i s gratefully acknowledged.
PY - 1991/12/30
Y1 - 1991/12/30
N2 - Representative 2,6-dideoxy sugars, l-cladinose (1), l-mycarose (2), l-oleandrose (3), l-olivose (4), and all of their C-3 epimers, 2,6-dideoxy-3-C-methyl-3-O-methyl-l-arabino-hexopyranose (26), 2,6-dideoxy-3-C-methyl-l-arabino-hexopyranose (l-olivomycose) (27), 2,6-dideoxy-3-O-methyl-l-ribo-hexopyranose (l-cymarose) (32), and 2,6-dideoxy-l-ribo-hexopyranose (l-digitoxose) (33) have been stereospecifically synthesized through a highly stereoselective addition of a nucleophilic reagent to the C-3 carbonyl groups of methyl 2,6-anhydro-4-O-benzyl-2-thio-α-l-arabino-hexopyranosid-3-ulose (11) or methyl 2,6-anhydro-4-O-benzyl-2-thio-β-l-arabino-hexopyranosid-3-ulose (12) possessing 2,6-anhydro-2-thio structures. Anomers 11 and 12 were both prepared in stereocontrolled fashion by treatment of a common intermediate, methyl 2,6-anhydro-4-O-benzyl-3-O-tetrahydropyranyl-2-thio-α-l-altropyranoside (8) with Lewis acids in methanol followed by oxidation.
AB - Representative 2,6-dideoxy sugars, l-cladinose (1), l-mycarose (2), l-oleandrose (3), l-olivose (4), and all of their C-3 epimers, 2,6-dideoxy-3-C-methyl-3-O-methyl-l-arabino-hexopyranose (26), 2,6-dideoxy-3-C-methyl-l-arabino-hexopyranose (l-olivomycose) (27), 2,6-dideoxy-3-O-methyl-l-ribo-hexopyranose (l-cymarose) (32), and 2,6-dideoxy-l-ribo-hexopyranose (l-digitoxose) (33) have been stereospecifically synthesized through a highly stereoselective addition of a nucleophilic reagent to the C-3 carbonyl groups of methyl 2,6-anhydro-4-O-benzyl-2-thio-α-l-arabino-hexopyranosid-3-ulose (11) or methyl 2,6-anhydro-4-O-benzyl-2-thio-β-l-arabino-hexopyranosid-3-ulose (12) possessing 2,6-anhydro-2-thio structures. Anomers 11 and 12 were both prepared in stereocontrolled fashion by treatment of a common intermediate, methyl 2,6-anhydro-4-O-benzyl-3-O-tetrahydropyranyl-2-thio-α-l-altropyranoside (8) with Lewis acids in methanol followed by oxidation.
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U2 - 10.1016/0008-6215(91)89016-9
DO - 10.1016/0008-6215(91)89016-9
M3 - Article
AN - SCOPUS:0026354522
SN - 0008-6215
VL - 222
SP - 173
EP - 188
JO - Carbohydrate Research
JF - Carbohydrate Research
IS - C
ER -