Diborane Reduction of O-(Tert-Butyldimethylsilyi.)galactaramides. A Model Study for Aminoalditol Synthesis

doi:10.1080/07328308608062958

Paper

Diborane Reduction of O-(Tert-Butyldimethylsilyi.)galactaramides. A Model Study for Aminoalditol Synthesis

Published Jun 1, 1986 · J. Navia, D. Kiely

Journal of Carbohydrate Chemistry

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Abstract

Abstract Tert-butyldimethylsilylation of dimethyl galactarate (1) with tert-butylchlorodimethylsilane/imidazole/N,N-dimethylformamide at 25 [ddot]C dimethyl 2,5-bis-O-(tert-butyldimethylsilyl)galactarate (2) as the principal product, with methyl 2,3,5-tris-O-(tert-butyldimethylsilyl)-D,L-galactarate-l,4-lactone (3) and methyl 2,3-bis-O-(tert-butyldimethyl)-D,L-galactarate-l,5-lactone (4) as minor products. When the reaction was carried out at 65 [ddot]C, the only product was the 1,4-lactone, 3 Ammonolysis of 2 in methanol gave 2,5-bis-O-(tert-butyldimethyl)-galactaramide (5, 94%), which was conveniently reduced with borane- THF to 1,6-diamino-1,6-dideoxygalactitol, isolated as its dihydrochloride 9. Ammonolysis of 3 in methanol gave a mixture of 5; 2,3,4-tris-O-(tert-butyldimethylsilyl)-D,L-galactaramide (6), 2,3,5-tris-O-(tert-butyldimethylsilyl)-D,L-galactaramide (7), and 2,3,5-tris-Q-(tert-butyldimethylsilyl)-D,L-1,4-lactonogalactaramide (8). Borane-THF reduction of a mixture of 6 and 7 also yielded 9....

Study Snapshot

Diborane-THF reduction of O-(tert-butyldimethylsilyl)-galactaramides can lead to 1,6-diamino-1,6-dideoxygalactitol, a promising intermediate for aminoalditol synthesis

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Diborane Reduction of O-(Tert-Butyldimethylsilyi.)galactaramides. A Model Study for Aminoalditol Synthesis

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References

The crystal structure of galactaric acid (mucic acid) at −147°: An unusually dense, hydrogen-bonded structure

Galactaric acid crystallizes at 147°, with strong hydrogen-bonds contributing to its high density and low solubility in water.

The formation of intermediate lactones during aminolysis of diethyl galactarate

Diethyl galactarate aminolysis involves intermediate -lactones, leading to galactaric diamide through competitive, consecutive, second-order kinetics.

Isomerization of tert-butyldimethylsilyl protecting groups in ribonucleosides

Tert-butyldimethylsilyl isomerization in ribonucleosides is most rapid in protic solvents and slow in solvents like dry dimethyl sulfoxide, pyridine, oxolane, chloroform, or N, N -di

Conformations in solution of the stereoisomeric, peracetylated aldohexose dimethyl acetals and diethyl dithioacetals

The conformations of acyclic carbohydrate derivatives with four contiguous asymmetric centers can be predicted using observations made for shorter-chain analogs.

Conformational analysis of peracetylated hexononitriles

Peracetylated hexononitriles generally have a zigzag conformation, with the cyano group in the plane of other carbon atoms, but other conformers are also possible.

Active polycondensation of diethyl 2,3,4,5‐tetrahydroxyadipate with diamines

Diethyl 2,3,4,5-tetrahydroxyadipate with diamines can rapidly produce linear polyamides with pendant hydroxyl groups, yielding high molecular weight polyamides under mild conditions.

Protection of hydroxyl groups as tert-butyldimethylsilyl derivatives

Dimethyl-tert-butylsilyl is a stable, hydroxyl-protecting agent with potential applications in various fields, including prostaglandin synthesis.

Citations

Synthetic polyhydroxypolyamides from galactaric, xylaric, D‐glucaric, and D‐mannaric acids and alkylenediamine monomers—some comparisons

Increased alkylenediamine monomer length decreases polyamide water solubility, with conformational differences in aldaryl units affecting polymer melting points and water solubilities.