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Adonitol
Conditions | Yield |
---|---|
Stage #1: C17H42O5Si4 With bis(pentafluorophenyl)borinic acid; 1,1,3,3-tetramethyldisilazane In 1,4-dioxane at 25℃; for 24h; Inert atmosphere; Glovebox; Stage #2: In methanol Inert atmosphere; Glovebox; chemoselective reaction; | 92% |
D-Ribose
Adonitol
Conditions | Yield |
---|---|
With methanol; lithium borohydride at 10 - 20℃; for 3h; Large scale; | 78% |
D-allose
Adonitol
Conditions | Yield |
---|---|
With 1-methyl-pyrrolidin-2-one; Wilkinson's catalyst at 130℃; | 50% |
DL-erythro-pentene-(1)-triol-(3.4.5)-triacetate
A
Adonitol
1,2,3,4,5-penta-O-acetyl-DL-arabinitol
Conditions | Yield |
---|---|
With osmium(VIII) oxide; silver(I) chlorate und Acetylierung des erhaltenen Gemisches von Ribit-1.2.3-triacetat und D-Arabit-3.4.5-triacetat Verseifen des Pentaacetats mit methylalkoh.HCl; |
Conditions | Yield |
---|---|
With sodium metaborate; water | |
With nickel; magnesium at 100℃; under 22065.2 Torr; Hydrogenation; | |
Yield given. Multistep reaction; |
L-ribose
Adonitol
Conditions | Yield |
---|---|
With sodium amalgam |
Adonitol
Conditions | Yield |
---|---|
With potassium acetate; acetic anhydride; acetic acid und Verseifen des entstandenen Pentaacetats mit siedender methylalkoh.HCl; |
D-Fructose
A
Adonitol
B
(S)-3,4-dihydroxy-butyraldehyde
C
2,3-dideoxy-3-C-hydroxymethyltetrose
D
2-deoxy-2-C-hydroxymethyltetrose
E
ethylene glycol
F
D-erythrose
Conditions | Yield |
---|---|
In water Quantum yield; Irradiation; 254-nm photolysis in deoxigenated and oxygenated solutions; |
Conditions | Yield |
---|---|
With sodium tetrahydroborate |
D-erythro-pentos-2-ulose
A
D-Arabitol
B
Adonitol
C
D-ribulose
D
D-ribose
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In water at 80℃; for 0.5h; | A n/a B n/a C 70 % Chromat. D n/a |
Conditions | Yield |
---|---|
With 4-nitroperbenzoic acid In dichloromethane at 90℃; |
4,5-O-isopropylidene-D-ribitol
Adonitol
Conditions | Yield |
---|---|
With Dowex 50X8-200 resin In water at 25℃; for 3h; | |
With hydrogenchloride |
(Z)-(4RS)-1,4,5-triacetoxypent-2-ene
Adonitol
Conditions | Yield |
---|---|
With pyridine; hydrogenchloride; tert.-butylhydroperoxide; osmium(VIII) oxide; tetraethylammonium acetate; acetic anhydride Yield given. Multistep reaction; |
(1R,2R)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-propane-1,2,3-triol
Adonitol
Conditions | Yield |
---|---|
With hydrogenchloride In methanol Heating; | |
With hydrogenchloride In methanol Heating; |
(1R,2R)-(S)-1-(1,4-Dioxa-spiro[4.5]dec-2-yl)-propane-1,2,3-triol
Adonitol
Conditions | Yield |
---|---|
With hydrogenchloride In methanol Heating; | |
With hydrogenchloride In methanol Heating; |
2,2-Dimethyl-propionic acid (2R,3R)-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,3-dihydroxy-propyl ester
Adonitol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In diethyl ether at 0℃; | |
Multi-step reaction with 2 steps 1: 5 percent conc HCl / methanol / Heating 2: LiAlH4 / diethyl ether / 0 °C View Scheme |
(2R,3R,4S)-4,5-Bis-benzyloxy-pentane-1,2,3-triol
Adonitol
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In methanol; acetic acid | |
With hydrogen; palladium on activated charcoal In methanol; acetic acid Ambient temperature; |
(1S,2S)-3-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-propane-1,2-diol
Adonitol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In diethyl ether at 0℃; | |
Multi-step reaction with 2 steps 1: 5 percent conc HCl / methanol / Heating 2: (n-Bu)4N(+)F(-) / tetrahydrofuran / Ambient temperature View Scheme |
Adonitol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In diethyl ether at 0℃; |
Adonitol
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran Ambient temperature; |
A
Adonitol
Conditions | Yield |
---|---|
With sodium hydroxide In water |
Conditions | Yield |
---|---|
With sodium hydroxide In water |
(2S,3S,4R)-5-((2R,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-pentane-1,2,3,4-tetraol
A
D-Glucose
B
Adonitol
Conditions | Yield |
---|---|
With sulfuric acid In 1,4-dioxane; water |
D-ribitol 5-phosphate
Adonitol
Conditions | Yield |
---|---|
Hydrolysis; |
arabinoic acid
A
meso-erythritol
B
D-Arabitol
C
XYLITOL
D
Adonitol
Conditions | Yield |
---|---|
With hydrogen; Ru-carbon In water at 80℃; under 45003.6 Torr; Product distribution; Further Variations:; Catalysts; pH-values; Temperatures; Reagents; |
Glycolaldehyde
Glyceraldehyde
A
D-threitol
B
D-Arabitol
C
XYLITOL
D
Adonitol
Conditions | Yield |
---|---|
Stage #1: Glycolaldehyde; Glyceraldehyde With zinc(II) bis(L-proline) In water at 20℃; for 168h; Stage #2: With sodium tetrahydroborate for 3h; Further byproducts given. Title compound not separated from byproducts; |
B
Adonitol
Conditions | Yield |
---|---|
With trifluoroacetic acid at 120℃; for 2h; |
Adonitol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: NaOMe / methanol 2: 5percent H2SO4 / H2O; dioxane View Scheme |
(1R,4'R)-1-(2,2-dimethyl-1,3-dioxolane-4-yl)-2-trimethylsilylprop-2-en-1-ol
Adonitol
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 85 percent / TBHP-VO(acac)2 2: 80 percent / t-BuOK, n-Bu4NF 3: 70 percent / NaOH / 70 °C 4: HCl View Scheme |
Adonitol
2,2-dimethoxy-propane
bis(2,2-dimethyl-1,3-dioxolan-4-yl)methanol
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In N,N-dimethyl-formamide Ambient temperature; | 99% |
With hydrogen cation In acetone for 2h; Ambient temperature; | 95% |
With toluene-4-sulfonic acid In N,N-dimethyl-formamide; acetone at 20℃; for 16h; Cyclization; | 85% |
Conditions | Yield |
---|---|
With 1-methyl-2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine In N,N-dimethyl-formamide at 25℃; for 24h; | 99% |
Conditions | Yield |
---|---|
With Sulfuric acid immobilized on silica gel at 20℃; for 0.333333h; neat (no solvent); | 98% |
With zinc(II) chloride anfangs unter Eiskuehlung; | |
With pyridine Ambient temperature; |
Adonitol
Conditions | Yield |
---|---|
With 1H-imidazole; thionyl chloride In tetrahydrofuran at -10℃; for 0.5h; | 98% |
Adonitol
LACTIC ACID
Conditions | Yield |
---|---|
With barium hydroxide octahydrate In methanol at 140℃; for 12h; Inert atmosphere; Sealed tube; | 93% |
With H2O*Ba8H16O16 In methanol at 140℃; for 12h; Sealed tube; | 88 %Chromat. |
Conditions | Yield |
---|---|
With potassium fluoride In dimethyl sulfoxide 1) 60 deg C, 10 h; 2) 90 deg C, 10 h; | 91% |
Adonitol
Conditions | Yield |
---|---|
With hydrogenchloride at 100℃; for 48h; | 90% |
With pyridine hydrochloride at 150℃; | 70% |
at 290℃; for 2h; | 45% |
With hydrogenchloride at 110℃; |
Adonitol
Conditions | Yield |
---|---|
With carbon tetrabromide; triphenylphosphine In N,N-dimethyl-formamide Ambient temperature; | 90% |
In water at 249.84℃; Kinetics; Temperature; Inert atmosphere; |
Conditions | Yield |
---|---|
In acetonitrile at 20℃; for 1.5h; Cooling with ice; | 88% |
Conditions | Yield |
---|---|
With pyridine at 100℃; for 22h; Inert atmosphere; | 85% |
With pyridine at 100℃; | |
With pyridine at 20℃; | |
With pyridine; dmap at 25℃; for 33h; | |
With pyridine; dmap at 20℃; for 30h; Inert atmosphere; |
Adonitol
acetone
1,2:3,4-Di-O-isopropylidene-DL-ribitol
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In various solvent(s) Ambient temperature; | 85% |
Adonitol
dichloromethylenedimethyliminium chloride
1,5-dichloro-1,5-dideoxy-2,4-di-O--ribitol
Conditions | Yield |
---|---|
In 1,4-dioxane at 25℃; for 2.5h; | 79% |
In 1,4-dioxane at 23℃; for 2.5h; | 79% |
Conditions | Yield |
---|---|
With hydrogenchloride In methanol; water for 8h; | 70% |
Conditions | Yield |
---|---|
Stage #1: Adonitol With di(n-butyl)tin oxide In toluene Stage #2: phenylcarbonochloridothioate In chloroform at 20℃; for 4h; | 63% |
Stage #1: Adonitol With di(n-butyl)tin oxide In toluene Heating; Stage #2: phenylcarbonochloridothioate In chloroform at 20℃; for 4h; | 63% |
Conditions | Yield |
---|---|
Stage #1: Adonitol With pyridine hydrochloride at 150℃; for 4h; Stage #2: 2,2-dimethoxy-propane With toluene-4-sulfonic acid In acetone at 20℃; for 0.5h; Stage #3: C22H22ClF3N2O4S Further stages; | 58% |
Adonitol
ribitol 3-O-(dichlorophosphite) 1,2;4,5-bis-O-(chlorophosphite)
Conditions | Yield |
---|---|
With phosphorus trichloride In 1,4-dioxane at 60 - 65℃; for 30h; | 57% |
Adonitol
acetic anhydride
benzyl bromide
A
penta-O-acetylribitol
Conditions | Yield |
---|---|
Stage #1: Adonitol With bis(tri-n-butyltin)oxide In toluene for 5h; Heating; Stage #2: benzyl bromide at 80℃; for 20h; Stage #3: acetic anhydride With pyridine at 20℃; | A 23% B 52% C 16% |
Adonitol
dichloromethylenedimethyliminium chloride
A
1,5-dichloro-1,5-dideoxy-2,4-di-O--ribitol
Conditions | Yield |
---|---|
In 1,4-dioxane at 23℃; for 26h; | A 47% B 20% |
Adonitol
dichloromethylenedimethyliminium chloride
A
1,5-dichloro-1,5-dideoxy-2,4-di-O--ribitol
Conditions | Yield |
---|---|
In 1,4-dioxane at 23℃; for 26h; | A 47% B 21% |
Adonitol
acetic anhydride
benzyl bromide
A
penta-O-acetylribitol
Conditions | Yield |
---|---|
Stage #1: Adonitol With di(n-butyl)tin oxide In toluene for 16h; Heating; Stage #2: benzyl bromide In chloroform at 65℃; for 65h; Stage #3: acetic anhydride With pyridine at 20℃; | A 47% B 10% C n/a D n/a |
Stage #1: Adonitol With di(n-butyl)tin oxide In toluene for 16h; Heating; Stage #2: benzyl bromide In chloroform at 50℃; for 40h; Stage #3: acetic anhydride With pyridine at 20℃; | A 32% B 31% C 8% D 17% |
Stage #1: Adonitol With di(n-butyl)tin oxide In toluene for 16h; Heating; Stage #2: benzyl bromide In chloroform at 65℃; for 65h; Stage #3: acetic anhydride With pyridine at 20℃; | A 16% B 26% C 11% D 20% |
Conditions | Yield |
---|---|
With (1S)-10-camphorsulfonic acid; phenylboronic acid In toluene at 120 - 130℃; for 24h; Inert atmosphere; Dean-Stark; | 47% |
Conditions | Yield |
---|---|
With (1S)-10-camphorsulfonic acid; phenylboronic acid In toluene at 120 - 130℃; for 24h; Inert atmosphere; Dean-Stark; | 44% |
Conditions | Yield |
---|---|
With C13H21O3Re at 135℃; for 15h; Reagent/catalyst; Inert atmosphere; | 42% |
Adonitol
triethyl phosphite
3-O-(diethyl phosphite)-1,2:4,5-bis-O-(ethyl phosphite)ribitol
Conditions | Yield |
---|---|
at 115 - 130℃; | 38% |
Adonitol
2-Methoxypropene
A
bis(2,2-dimethyl-1,3-dioxolan-4-yl)methanol
1,4:2,3-di-O-isopropylidene-DL-ribitol
1,3:4,5-di-O-isopropylidene-DL-ribitol
1,3:2,5-di-O-isopropylidene-DL-ribitol
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 0℃; for 0.0166667h; | A 36% B 3% C 12% D 5% |
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 0℃; for 0.0166667h; Product distribution; | A 36% B 3% C 12% D 5% |
Conditions | Yield |
---|---|
With methyltrioxorhenium(VII) at 170℃; for 3h; | 33% |
Adonitol
3,4-bis(decyloxy)benzoic acid
Conditions | Yield |
---|---|
With dmap In dichloromethane at 20℃; for 72h; Esterification; | 8% |
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