TY - JOUR
T1 - Glycosyl Bunte Salts
T2 - A Class of Intermediates for Sugar Chemistry
AU - Meguro, Yasuhiro
AU - Noguchi, Masato
AU - Li, Gefei
AU - Shoda, Shin Ichiro
N1 - Funding Information:
This work was supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology, Japan. We thank Mr. Ryohei Hayasaka for experimental support.
Publisher Copyright:
© 2017 American Chemical Society.
PY - 2018/1/5
Y1 - 2018/1/5
N2 - S-Glycosyl thiosulfates have been discovered as a new class of synthetic intermediates in sugar chemistry, named "glycosyl Bunte salts" after 19th-century German chemist, Hans Bunte. The synthesis was achieved by direct condensation of unprotected sugars and sodium thiosulfate using a formamidine-type dehydrating agent in water-acetonitrile mixed solvent. The application of glycosyl Bunte salts is demonstrated with transformation reactions into other glycosyl compounds such as a 1-thio sugar, a glycosyl disulfide, a 1,6-anhydro sugar, and an O-glycoside.
AB - S-Glycosyl thiosulfates have been discovered as a new class of synthetic intermediates in sugar chemistry, named "glycosyl Bunte salts" after 19th-century German chemist, Hans Bunte. The synthesis was achieved by direct condensation of unprotected sugars and sodium thiosulfate using a formamidine-type dehydrating agent in water-acetonitrile mixed solvent. The application of glycosyl Bunte salts is demonstrated with transformation reactions into other glycosyl compounds such as a 1-thio sugar, a glycosyl disulfide, a 1,6-anhydro sugar, and an O-glycoside.
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U2 - 10.1021/acs.orglett.7b03400
DO - 10.1021/acs.orglett.7b03400
M3 - Article
C2 - 29243482
AN - SCOPUS:85040249841
SN - 1523-7060
VL - 20
SP - 76
EP - 79
JO - Organic Letters
JF - Organic Letters
IS - 1
ER -