scholarly journals Acetyl Group Migration across the Saccharide Units in Oligomannoside Model Compound

2018 ◽  
Vol 141 (4) ◽  
pp. 1646-1654 ◽  
Author(s):  
Robert Lassfolk ◽  
Jani Rahkila ◽  
Mikael P. Johansson ◽  
Filip S. Ekholm ◽  
Johan Wärnå ◽  
...  
ChemBioChem ◽  
2021 ◽  
Author(s):  
Robert Lassfolk ◽  
Sara Bertuzzi ◽  
Ana Ardá ◽  
Johan Wärnå ◽  
Jesús Jiménez‐Barbero ◽  
...  

2020 ◽  
Vol 83 (4) ◽  
pp. 888-893 ◽  
Author(s):  
Dariya A. Romanova ◽  
David L. Avetyan ◽  
Maxim L. Belyanin ◽  
Elena V. Stepanova

2020 ◽  
Vol 232 ◽  
pp. 115783 ◽  
Author(s):  
Vladimír Puchart ◽  
Morten Gjermansen ◽  
Mária Mastihubová ◽  
Kristian B.R. Mørkeberg Krogh ◽  
Peter Biely

1981 ◽  
Vol 54 (4) ◽  
pp. 1077-1084 ◽  
Author(s):  
Toshihiko Uchiyama ◽  
Kazuhiko Takagi ◽  
Keiji Matsumoto ◽  
Shun’ichiro Ooi ◽  
Yukio Nakamura ◽  
...  
Keyword(s):  

1970 ◽  
Vol 48 (8) ◽  
pp. 1302-1308 ◽  
Author(s):  
Hans H. Baer ◽  
Werner Rank ◽  
Frank Kienzle

Starting from methyl 3-deoxy-3-nitro-β-D-glucopyranoside (1), the free sugar 3-deoxy-3-nitro-α-D-glucopyranose (2), its tetraacetate (3), and 2,4,6-tri-O-acetyl-3-deoxy-3-nitro-α-D-glucopyranosyl bromide (4) were prepared. Another sequence of reactions commencing with 1 gave the 6-O-trityl (6), the 2,4-di-O-acetyl-6-O-trityl (7), the 2,4,6-tri-O-acetyl (8), and the 2,6-di-O-acetyl (10) derivatives of 1, whereas the 2,4-di-O-acetyl derivative (9) could not be isolated in pure form because of acetyl group migration. Reaction of the bromide 4 with water, methanol, and benzyl alcohol, respectively, led to 2,4,6-tri-O-acetyl-3-deoxy-3-nitro-β-D-glucopyranose (5) and the corresponding methyl and benzyl β-D-glycosides (8 and 11). Condensation of 4 with 1,2,3,4-tetra-O-acetyl-β-D-glucopyranose (12), and condensation of tetra-O-acetyl-α-D-glucopyranosyl bromide (14) with the trityl compound 6, furnished derivatives of gentiobiose having a deoxynitro function at C-3′ (13) and C-3 (15), respectively.


1957 ◽  
Vol 35 (1) ◽  
pp. 30-38 ◽  
Author(s):  
G. G. McKeown ◽  
R. S. E. Serenius ◽  
L. D. Hayward

Sucrose was tritylated and acetylated to give a crystalline tri-O-trityl-penta-O-acetyl sucrose derivative, and detritylation of this product by graded hydrolysis with acetic acid followed by methylation and deacetylation yielded 1′,4,6′-tri-O-methyl sucrose. The structure of the tri-O-methyl sucrose was established by periodate oxidation and by hydrolysis to the corresponding O-methyl ethers of glucose and fructose. Acetyl group migration from C4 to C6 in the glucose moiety of sucrose probably occurred during the methylation reaction.Some aspects of syntheses involving sucrose are discussed.


1984 ◽  
Vol 135 (1) ◽  
pp. 129-140 ◽  
Author(s):  
Fany Reicher ◽  
João B.C. Corrêa ◽  
Philip A.J. Gorin
Keyword(s):  

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