754. Phosphorylated sugars. Part VII. Acid-catalysed acetyl group migration in 1,2,3,4,6-penta-O-acetyl-β-D-glycero-D-galacto-heptose and the synthesis ofD-glycero-D-galacto-heptose-6-phosphate

1963 ◽  
Vol 0 (0) ◽  
pp. 3970-3975 ◽  
Author(s):  
Donald R. Strobach ◽  
L. Szabó
Keyword(s):  
Acetyl Group ◽  
Group Migration ◽  
Phosphorylated Sugars

scholarly journals Kinetic Studies of Acetyl Group Migration between the Saccharide Units in an Oligomannoside Trisaccharide Model Compound and a Native Galactoglucomannan Polysaccharide

ChemBioChem ◽  
2021 ◽  
Author(s):  
Robert Lassfolk ◽  
Sara Bertuzzi ◽  
Ana Ardá ◽  
Johan Wärnå ◽  
Jesús Jiménez‐Barbero ◽  
...  
Keyword(s):  
Model Compound ◽  
Kinetic Studies ◽  
Acetyl Group ◽  
Group Migration

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 ◽  
...  
Keyword(s):  
Model Compound ◽  
Acetyl Group ◽  
Group Migration

Synthesis of Salicaceae Acetyl Salicins Using Selective Deacetylation and Acetyl Group Migration

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

Positional specificity of Flavobacterium johnsoniae acetylxylan esterase and acetyl group migration on xylan main chain

2020 ◽  
Vol 232 ◽  
pp. 115783 ◽  
Author(s):  
Vladimír Puchart ◽  
Morten Gjermansen ◽  
Mária Mastihubová ◽  
Kristian B.R. Mørkeberg Krogh ◽  
Peter Biely
Keyword(s):  
Main Chain ◽  
Positional Specificity ◽  
Flavobacterium Johnsoniae ◽  
Acetylxylan Esterase ◽  
Acetyl Group ◽  
Group Migration

scholarly journals Reactions oftrans- andcis-Dichlorobis(benzonitrile)platinum(II) with Acetylacetonate and Benzoylacetonate Carbanions. Formation ofN-Acetyl β-Ketoamine Complexes by the Acetyl Group Migration

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

Reactions of nitro sugars. XVII. Koenigs–Knorr syntheses

1970 ◽  
Vol 48 (8) ◽  
pp. 1302-1308 ◽  
Author(s):  
Hans H. Baer ◽  
Werner Rank ◽  
Frank Kienzle
Keyword(s):  
Benzyl Alcohol ◽  
Acetyl Derivative ◽  
Pure Form ◽  
Free Sugar ◽  
Acetyl Group ◽  
Group Migration ◽  
Derivatives Of

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.

SELECTIVE SUBSTITUTION IN SUCROSE: I. THE SYNTHESIS OF 1′,4,6′-TRI-O-METHYL SUCROSE

1957 ◽  
Vol 35 (1) ◽  
pp. 30-38 ◽  
Author(s):  
G. G. McKeown ◽  
R. S. E. Serenius ◽  
L. D. Hayward
Keyword(s):  
Acetic Acid ◽  
Periodate Oxidation ◽  
Selective Substitution ◽  
Acetyl Group ◽  
Group Migration

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.

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