A Convenient Preparative Method of Carbohydrate Phosphates With Butyllithium and Phosphorochloridate

Inage, Masaru; Chaki, Haruyuki; Kusumoto, Shoichi; Shiba, Tetsuo

doi:10.1246/cl.1982.1281

Cited by 74 publications

(27 citation statements)

References 5 publications

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“…decanoyloxytetradecanamido]-l-thio-B-~-glucopyranose (9) and its 1-S-tetradecanoyl derivative (10) in 76 and 61% yield, respectively. …”

Section: Acetyl-2-deoxy-4-~-phosphono-3-~-tetradecanoyl-2-[(3~)-3-tetra-mentioning

confidence: 99%

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The Chemical Modification of the C-1 Substituent of A 4-O-Phosphono-O-Glucosamine Derivative (GLA-27) Related to Bacterial Lipid A

Ogawa

Fujishima

Konishi

et al. 1987

Journal of Carbohydrate Chemistry

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“…decanoyloxytetradecanamido]-l-thio-B-~-glucopyranose (9) and its 1-S-tetradecanoyl derivative (10) in 76 and 61% yield, respectively. …”

Section: Acetyl-2-deoxy-4-~-phosphono-3-~-tetradecanoyl-2-[(3~)-3-tetra-mentioning

confidence: 99%

“…Found: C, 52.85;H, 7.70;N, 0.94. Anal. ( 9 ) . To a solution of compound 1 (0.2 g) in acetic acid (5 mL) was added zinc dust (1 g), and the mixture was stirred overnight at room temperature.…”

Section: L-s-acetvl-2-deoxy-46-o-isoprop~lidene-3-o-tetradecanoyl-2-mentioning

confidence: 99%

The Chemical Modification of the C-1 Substituent of A 4-O-Phosphono-O-Glucosamine Derivative (GLA-27) Related to Bacterial Lipid A

Ogawa

Fujishima

Konishi

et al. 1987

Journal of Carbohydrate Chemistry

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“…In the first one, phosphoric acid, their salts, or dialkyl phosphates were used as nucleophiles on glycose peracetates (2), 1 ,2-orthoesters (3), halogenoses (4), 1,2-oxazolines (5), Brig1 anhydrides (6), or on trichloroacetimidates (7). In the second approach, the anomeric hydroxyl groups were activated as lithium (8) or thallium (9) salts and reacted with electrophilic dialkyl phosphorochloridates. More recently, the phosphorarnidite and H-phosphonate methods have also attracted interest (10).…”

Section: Introductionmentioning

confidence: 99%

Syntheses of glycosyl phosphates by phase transfer catalysis

Roy¹,

Tropper²,

Grand‐Maître³

1991

Can. J. Chem.

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R E N~ ROY, FRANGOIS D. TROPPER, and CHANTAL GRAND-MAITRE. Can. J. Chem. 69, 1462Chem. 69, (1991. The peracetylated glycosyl bromides of D-glucose (I), D-galactose (2), and D-lactose (5) were treated with dibenzyl phosphate in a catalytic two-phase system using tetrabutylammonium hydrogen sulfate as catalyst. The reactions proceeded by complete inversion at the anomeric centers and afforded a new stereospecific entry into 1 ,2-trans-P-D-glycosyl phosphates of peracetylated D-glucose (3), D-galactose (4), and the disaccharide D-lactose (6) in 83, 73, and 83% yields respectively. Interestingly, the glycosyl chloride 7 furnished the oxazoline 9 rather than the expected glycosyl phosphate 8.

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“…Finally, the 1-O-a-phosphorylation was carried out via 1-O-lithiation and subsequent treatment with tetrabenzyl diphosphate in THF at -78 °C. 8,18 The protected 1,4'-bisphosphate 7 thus obtained was purified by silica-gel column chromatography. Subsequently, all the protecting groups of 7 were removed by hydrogenolysis (10 kgcm -2 of H 2 ) with Pd-black in one-step.…”

mentioning

confidence: 99%

New Efficient Route for Synthesis of Lipid A by using Affinity Separation

Fukase¹,

Zhang²,

Iseki³

et al. 2001

Synlett

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New efficient synthesis of lipid A, an immunostimulating glycoconjugate of bacteria, was achieved for the construction of lipid A library by using synthesis based on affinity separation (SAS), where the compounds possessing a barbituric acid (BA)-tag are selectively and rapidly purified by interaction with an artificial receptor for BA. Glycosylation of a glycosyl acceptor possessing the BA-tag with a 4'-phosphorylated N-Troc glucosaminyl trichloroacetimidate gave the disaccharide 4'-phosphate, which was purified by the affinity separation. Successive removal of protective groups and introduction of acyl groups were then effected and the synthetic intermediate at each step was purified by the affinity separation. Cleavage of the tag and subsequent deprotection afforded Escherichia coli lipid A. SAS enabled the rapid preparation of lipid A, therefore, proved to be a promising method for synthesis of other complex glycoconjugates.

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A Convenient Preparative Method of Carbohydrate Phosphates With Butyllithium and Phosphorochloridate

Abstract: α-Glycosyl phosphates and 4-phosphates of N-acylglucosamine derivatives were prepared in high yields via the reaction of corresponding O-lithium salts with dibenzyl or diphenyl phosphorochloridate at low temperature.

Cited by 74 publications

References 5 publications

The Chemical Modification of the C-1 Substituent of A 4-O-Phosphono-O-Glucosamine Derivative (GLA-27) Related to Bacterial Lipid A

The Chemical Modification of the C-1 Substituent of A 4-O-Phosphono-O-Glucosamine Derivative (GLA-27) Related to Bacterial Lipid A

Syntheses of glycosyl phosphates by phase transfer catalysis

New Efficient Route for Synthesis of Lipid A by using Affinity Separation

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