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CAS No.: | 53185-12-9 |
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Name: | fagomine |
Article Data: | 24 |
Molecular Structure: | |
Formula: | C6H13 N O3 |
Molecular Weight: | 147.174 |
Synonyms: | 3,4-Piperidinediol,2-(hydroxymethyl)-, [2R-(2a,3b,4a)]-; 1,2,5-Trideoxy-1,5-imino-D-arabino-hexitol;D-Fagomine; Fagomine |
Density: | 1.279g/cm3 |
Melting Point: | 185-186℃ |
Boiling Point: | 315.4°Cat760mmHg |
Flash Point: | 170.5°C |
PSA: | 72.72000 |
LogP: | -1.60880 |
D-fagomine
Conditions | Yield |
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With triethylsilane; palladium on activated charcoal; hydrogen In ethanol at 20℃; | 100% |
(2R,3R,4R)-benzyl 3,4-bis(benzyloxy)-2-(hydroxymethyl)piperidine-1-carboxylate
D-fagomine
Conditions | Yield |
---|---|
With hydrogenchloride; palladium on activated charcoal; hydrogen In ethanol; water for 12h; Inert atmosphere; | 95% |
(2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)piperidine
D-fagomine
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen; acetic acid at 27℃; for 12h; | 87% |
With hydrogenchloride; palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 2585.81 Torr; for 18h; | 82% |
(4aR,8R,8aR)-tert-butyl hexahydro-8-hydroxy-2,2-dimethyl[1,3]dioxino[5,4-b]pyridine-5-carboxylate
D-fagomine
Conditions | Yield |
---|---|
Stage #1: (4aR,8R,8aR)-tert-butyl hexahydro-8-hydroxy-2,2-dimethyl[1,3]dioxino[5,4-b]pyridine-5-carboxylate With hydrogenchloride In methanol; water at 60℃; for 2h; Stage #2: With DOWEX-50wX8 Further stages.; | 83% |
With hydrogenchloride In methanol; ethyl acetate for 2h; |
(3S,4R)-6-[(benzyloxycarbonyl)amino]-5,6-dideoxy-2-hexulose
A
D-fagomine
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In ethanol; water at 20℃; under 2585.81 Torr; | A 83% B n/a |
(1S,2R,6R)-2-(tert-butyldiphenylsilanyloxymethyl)-7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylic acid tert-butyl ester
A
D-fagomine
Conditions | Yield |
---|---|
Stage #1: (1S,2R,6R)-2-(tert-butyldiphenylsilanyloxymethyl)-7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylic acid tert-butyl ester With potassium hydroxide In 1,4-dioxane Stage #2: With hydrogenchloride In methanol at 60℃; for 1h; | A 17% B 82% |
With sulfuric acid In 1,4-dioxane; water | A 44% B 33% |
With sulfuric acid In 1,4-dioxane; water at 95℃; for 3h; | A 44% B 33% |
(2R,3R,4R)-3-(tert-butyldimethylsilyloxy)-2-((tert-butyldimethylsilyloxy)methyl)piperidin-4-ol
D-fagomine
Conditions | Yield |
---|---|
With hydrogenchloride; water at 20℃; for 24h; | 82% |
5,6-dideoxy-6(trifluoroacetamido)-D-threo-hexulose
D-fagomine
Conditions | Yield |
---|---|
With 10 wt% Pd(OH)2 on carbon; hydrogen; potassium carbonate In water under 2585.81 Torr; | 81% |
(2S,3R,4R)-1-benzyl-3,4-bis(benzyloxy)-2-[(benzyloxy)methyl]piperidine
D-fagomine
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 2585.81 Torr; for 24h; | 80% |
(1R,2R,6S)-2-(tert-butyldiphenylsilanyloxymethyl)-7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylic acid tert-butyl ester
D-fagomine
Conditions | Yield |
---|---|
With sulfuric acid In 1,4-dioxane; water | 75% |
With sulfuric acid In 1,4-dioxane; water at 95℃; for 3h; | 75% |