1-O-Acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose supplier

Name
beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate
EINECS 230-220-4
CAS No. 6974-32-9
Article Data48
CAS DataBase
Density 1.35 g/cm³
Solubility
Melting Point 128-130 °C
Formula C₂₈H₂₄O₉
Boiling Point 621 °C at 760 mmHg
Molecular Weight 504.493
Flash Point 264.3 °C
Transport Information
Appearance white to light yellow crystal powder
Safety 22-24/25-37/39-26
Risk Codes 36/38
Molecular Structure
Hazard Symbols Xi
Synonyms Ribofuranose,1-acetate 2,3,5-tribenzoate, b-D- (6CI,8CI);1-O-Acetyl-2,3,4-tri-O-benzoyl-b-D-ribofuranose;1-O-Acetyl-2,3,5-tri-O-benzoyl-b-D-ribofuranose;1-O-Acetyl-2,3,5-tri-O-benzoyl-b-D-ribose;1-O-Acetyltri-O-benzoyl-b-D-ribofuranose;2,3,5-Tri-O-benzoyl-b-D-ribofuranosylacetate;ABR;NSC 23349;1-O-Acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose;1-O-Acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose;
PSA 114.43000
LogP 3.58260

Synthetic route

: 52783-53-6
methyl 2,3,3'-tri-O-benzoyl-β-D-apiofuranoside

: 108-24-7
acetic anhydride

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

Conditions

Conditions	Yield
With sulfuric acid; acetic acid at 20℃; for 0.5h;	95%
With sulfuric acid In ethyl acetate at 50 - 60℃;	30 g
With sulfuric acid In acetic acid at 0 - 20℃; for 5h;

: 108-24-7
acetic anhydride

: 115459-50-2
2,3,5-Tri-O-benzoyl-D-ribofuranose

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

Conditions

Conditions	Yield
With pyridine at 40℃; Cooling with ice;	92.1%
With sulfuric acid; acetic acid	78%
With sulfuric acid; acetic acid 1.) 0-5 deg C, 0.5 h, 2.) 20 deg C, 1 h;	74%

: 108-24-7
acetic anhydride

: 62374-23-6
N6,N6,2',3',5'-pentabenzoyl-β-D-adenosine

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane at 10 - 20℃; for 12h;	70.9%

: 22224-38-0
1,2,3,5-tetra-O-benzoyl-β-D-ribofuranose

: 108-24-7
acetic anhydride

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate at 0℃; for 1h;	51%
With zinc(II) chloride
With boron fluoride ether

: 55797-81-4
O2,O3,O5-Tribenzoyl-D-ribose

: 108-24-7
acetic anhydride

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

Conditions

Conditions	Yield
With pyridine

: 67-56-1
methanol

: 50-69-1
D-ribose

: 98-88-4
benzoyl chloride

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

Conditions

Conditions	Yield
With pyridine; hydrogenchloride; dichloromethane Behandeln der gebildeten Benzoyl-Derivate mit Bromwasserstoff in Essigsaeure und Behandeln in Chloroform mit Acetanhydrid und Pyridin;
With pyridine; hydrogenchloride; chloroform Behandeln des danach isolierten Reaktionsprodukts mit Acetanhydrid und Essigsaeure unter Zusatz von Schwefelsaeure;

...Expand

: 98-88-4
benzoyl chloride

: 102474-34-0
O1-Acetyl-O2,O5-dibenzoyl-β-D-ribofuranose

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

Conditions

Conditions	Yield
With pyridine

: 58-61-7
adenosine

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

Conditions

Conditions	Yield
durch partielle Benzoylierung, Hydrolyse (wss. Schwefelsaeure) und Acetylierung dargestellt;

: 67525-66-0
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

: 108-24-7
acetic anhydride

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

Conditions

Conditions	Yield
With pyridine Ambient temperature; Yield given;

: 108-24-7
acetic anhydride

: 69350-76-1
methyl 2,3,5-tri-O-benzoyl-αβ-D-ribofuranoside

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

Conditions

Conditions	Yield
With sulfuric acid; acetic acid at 4 - 5℃; Yield given;
With sulfuric acid; acetic acid at -5℃; for 10h; Inert atmosphere;	29.8 g
With sulfuric acid In acetic acid at 0 - 20℃; for 5h;	6 g

: 50-69-1
D-ribose

: 98-88-4
benzoyl chloride

: 64-19-7
acetic acid

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

Conditions

Conditions	Yield
Yield given. Multistep reaction;

...Expand

: 123-91-1
1,4-dioxane

: 111-43-3
Dipropyl ether

: 7664-93-9
sulfuric acid

: 66048-53-1
2',3',5'-tri-O-benzoylguanosine

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

Conditions

Conditions	Yield
anschliessend Behandeln mit Acetanhydrid und Pyridin;

...Expand

guanosine: guanosine

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

Conditions

Conditions	Yield
durch partielle Benzoylierung, Hydrolyse (wss. Schwefelsaeure) und Acetylierung dargestellt;

: 5517-61-3
methyl 3'-O-benzoyl-β-D-apiofuranoside

A: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

B 4-methylbenzimidazole N-trimethylsilyl derivative: 4-methylbenzimidazole N-trimethylsilyl derivative

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 89 percent / DMAP; pyridine / 50 °C 2: 95 percent / AcOH; H2SO4 / 0.5 h / 20 °C View Scheme

: 5517-60-2
methyl 3'-O-benzoyl-2,3-O-isopropylidene-β-D-apiofuranoside

A: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

B 4-methylbenzimidazole N-trimethylsilyl derivative: 4-methylbenzimidazole N-trimethylsilyl derivative

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 87 percent / Dowex 50H+ / methanol / 48 h / 60 °C 2: 89 percent / DMAP; pyridine / 50 °C 3: 95 percent / AcOH; H2SO4 / 0.5 h / 20 °C View Scheme

: 4099-85-8
((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol

A: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

B 4-methylbenzimidazole N-trimethylsilyl derivative: 4-methylbenzimidazole N-trimethylsilyl derivative

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 92 percent / pyridine / 5 h / 20 °C 2: 87 percent / Dowex 50H+ / methanol / 48 h / 60 °C 3: 89 percent / DMAP; pyridine / 50 °C 4: 95 percent / AcOH; H2SO4 / 0.5 h / 20 °C View Scheme

: 98-88-4
benzoyl chloride

6-t-butyl-12-p-tolyl-5,6,7,12-tetrahydrodibenz[c,f][1,5]azastibocine: 6-t-butyl-12-p-tolyl-5,6,7,12-tetrahydrodibenz[c,f][1,5]azastibocine

A: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

B 4-methylbenzimidazole N-trimethylsilyl derivative: 4-methylbenzimidazole N-trimethylsilyl derivative

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 92 percent / pyridine / 5 h / 20 °C 2: 87 percent / Dowex 50H+ / methanol / 48 h / 60 °C 3: 89 percent / DMAP; pyridine / 50 °C 4: 95 percent / AcOH; H2SO4 / 0.5 h / 20 °C View Scheme

...Expand

: 16205-60-0
2,3,5-tri-O-benzoyl-β-D-ribofuranosyl bromide

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: water / CH2Cl2 2: 78 percent / sulfuric acid, acetic acid View Scheme

: 1824-96-0, 1824-97-1, 3795-68-4, 3795-69-5, 4229-54-3, 5531-18-0, 7473-45-2, 13039-63-9, 13039-64-0, 13039-65-1, 13039-67-3, 22416-73-5, 22861-09-2, 25129-51-5, 52485-92-4, 52689-55-1, 52689-56-2, 56607-40-0, 72880-70-7, 79083-42-4, 86782-30-1, 86782-31-2, 89615-03-2, 89673-67-6, 89707-99-3, 102045-32-9, 135910-17-7
methyl ribofuranoside

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / CH2Cl2 / 1) 0-5 deg C, 4 h, 2) 4-5 deg C, 12 h 2: AcOH, conc. H2SO4 / 4 - 5 °C View Scheme
Multi-step reaction with 2 steps 1: pyridine / 3 h / 80 °C / Cooling with ice; Inert atmosphere 2: sulfuric acid; acetic acid / 10 h / -5 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: pyridine / 12 h / 0 - 20 °C 2: sulfuric acid / acetic acid / 5 h / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: pyridine / 12 h / 0 - 20 °C 2: sulfuric acid / acetic acid / 5 h / 0 - 20 °C View Scheme

: 532-20-7, 613-83-2, 7261-25-8, 7687-39-0, 13221-22-2, 14795-83-6, 15761-67-8, 20074-49-1, 25545-03-3, 25545-04-4, 32445-75-3, 34436-17-4, 36441-93-7, 36468-53-8, 37110-85-3, 37388-49-1, 38029-69-5, 40461-77-6, 40461-89-0, 41546-19-4, 41546-20-7, 41546-21-8, 41546-26-3, 41546-29-6, 41546-30-9, 41546-31-0, 126872-16-0, 131064-98-7
D-Ribose

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: KU-2-8 cation-exchange resin (H(1+)-form) / 2 h 2: pyridine / CH2Cl2 / 1) 0-5 deg C, 4 h, 2) 4-5 deg C, 12 h 3: AcOH, conc. H2SO4 / 4 - 5 °C View Scheme
Multi-step reaction with 3 steps 1: sulfuric acid / 5 h / 20 °C 2: pyridine / 12 h / 0 - 20 °C 3: sulfuric acid / acetic acid / 5 h / 0 - 20 °C View Scheme

: 52783-53-6
methyl 2,3,3'-tri-O-benzoyl-β-D-apiofuranoside

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: conc. HCl / dioxane / 1 h / 100 °C 2: pyridine / Ambient temperature View Scheme

: 36468-53-8
β-D-ribofuranose

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: HCl / Ambient temperature 2: pyridine / Ambient temperature 3: conc. HCl / dioxane / 1 h / 100 °C 4: pyridine / Ambient temperature View Scheme
Multi-step reaction with 3 steps 1.1: toluene-4-sulfonic acid / 30 - 50 °C 2.1: triethylamine; dmap / 1,2-dichloro-ethane 2.2: 30 °C 3.1: sulfuric acid / 20 °C View Scheme
Multi-step reaction with 3 steps 1.1: toluene-4-sulfonic acid / 30 - 50 °C 2.1: triethylamine; dmap / 1,2-dichloro-ethane 2.2: 30 °C 3.1: sulfuric acid / ethyl acetate / 50 - 60 °C View Scheme

: 98-88-4
benzoyl chloride

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine / Ambient temperature 2: conc. HCl / dioxane / 1 h / 100 °C 3: pyridine / Ambient temperature View Scheme
Multi-step reaction with 3 steps 1: pyridine 2: palladium/charcoal; ethyl acetate / Hydrogenation 3: pyridine View Scheme
Multi-step reaction with 2 steps 1: methanol. HCl; pyridine; HBr / weiteres Reagens: Ag2CO3; Reaktion ueber mehrere Stufen 2: pyridine View Scheme

: 7473-45-2
1-O-methyl-D-ribofuranose

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine / Ambient temperature 2: conc. HCl / dioxane / 1 h / 100 °C 3: pyridine / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1.1: triethylamine; dmap / 1,2-dichloro-ethane 1.2: 30 °C 2.1: sulfuric acid / ethyl acetate / 50 - 60 °C View Scheme

: 532-31-0
silver benzoate

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: benzene 2: pyridine 3: boron fluoride ether adduct View Scheme

: 59556-69-3
2,3,5-tri-O-benzoyl-1-O-benzyl-β-D-ribofuranose

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: palladium/charcoal; ethyl acetate / Hydrogenation 2: pyridine View Scheme

: 98796-65-7
O1,O3,O5-Tribenzoyl-β-D-ribofuranose

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine 2: boron fluoride ether adduct View Scheme

: 2280-44-6
D-Glucose

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1.1: sulfuric acid 2.1: chromium(VI) oxide; pyridine; acetic anhydride / dichloromethane / 0.42 h / Cooling with ice 3.1: sodium tetrahydroborate; ethanol / Cooling with ice 4.1: periodic acid / ethyl acetate / 2 h 5.1: sodium tetrahydroborate; ethanol / 3 h / Cooling with ice 6.1: acetic acid / 3 h / 80 °C 6.2: 18 h / Cooling with ice 7.1: pyridine / 3 h / 80 °C / Cooling with ice; Inert atmosphere 8.1: sulfuric acid; acetic acid / 10 h / -5 °C / Inert atmosphere View Scheme
Multi-step reaction with 9 steps 1.1: sulfuric acid 2.1: chromium(VI) oxide; pyridine; acetic anhydride / dichloromethane / 0.42 h / Cooling with ice 3.1: sodium tetrahydroborate; ethanol / Cooling with ice 4.1: sulfuric acid / methanol 5.1: sodium periodate / ethanol; water / 4 h 6.1: sodium tetrahydroborate; ethanol / 3 h / Cooling with ice 7.1: acetic acid / 3 h / 80 °C 7.2: 18 h / Cooling with ice 8.1: pyridine / 3 h / 80 °C / Cooling with ice; Inert atmosphere 9.1: sulfuric acid; acetic acid / 10 h / -5 °C / Inert atmosphere View Scheme

Yield

Multi-step reaction with 8 steps
1.1: sulfuric acid
2.1: chromium(VI) oxide; pyridine; acetic anhydride / dichloromethane / 0.42 h / Cooling with ice
3.1: sodium tetrahydroborate; ethanol / Cooling with ice
4.1: periodic acid / ethyl acetate / 2 h
5.1: sodium tetrahydroborate; ethanol / 3 h / Cooling with ice
6.1: acetic acid / 3 h / 80 °C
6.2: 18 h / Cooling with ice
7.1: pyridine / 3 h / 80 °C / Cooling with ice; Inert atmosphere
8.1: sulfuric acid; acetic acid / 10 h / -5 °C / Inert atmosphere
View Scheme

Multi-step reaction with 9 steps
1.1: sulfuric acid
2.1: chromium(VI) oxide; pyridine; acetic anhydride / dichloromethane / 0.42 h / Cooling with ice
3.1: sodium tetrahydroborate; ethanol / Cooling with ice
4.1: sulfuric acid / methanol
5.1: sodium periodate / ethanol; water / 4 h
6.1: sodium tetrahydroborate; ethanol / 3 h / Cooling with ice
7.1: acetic acid / 3 h / 80 °C
7.2: 18 h / Cooling with ice
8.1: pyridine / 3 h / 80 °C / Cooling with ice; Inert atmosphere
9.1: sulfuric acid; acetic acid / 10 h / -5 °C / Inert atmosphere
View Scheme

: 582-52-5
1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: chromium(VI) oxide; pyridine; acetic anhydride / dichloromethane / 0.42 h / Cooling with ice 2.1: sodium tetrahydroborate; ethanol / Cooling with ice 3.1: periodic acid / ethyl acetate / 2 h 4.1: sodium tetrahydroborate; ethanol / 3 h / Cooling with ice 5.1: acetic acid / 3 h / 80 °C 5.2: 18 h / Cooling with ice 6.1: pyridine / 3 h / 80 °C / Cooling with ice; Inert atmosphere 7.1: sulfuric acid; acetic acid / 10 h / -5 °C / Inert atmosphere View Scheme
Multi-step reaction with 8 steps 1.1: chromium(VI) oxide; pyridine; acetic anhydride / dichloromethane / 0.42 h / Cooling with ice 2.1: sodium tetrahydroborate; ethanol / Cooling with ice 3.1: sulfuric acid / methanol 4.1: sodium periodate / ethanol; water / 4 h 5.1: sodium tetrahydroborate; ethanol / 3 h / Cooling with ice 6.1: acetic acid / 3 h / 80 °C 6.2: 18 h / Cooling with ice 7.1: pyridine / 3 h / 80 °C / Cooling with ice; Inert atmosphere 8.1: sulfuric acid; acetic acid / 10 h / -5 °C / Inert atmosphere View Scheme

Yield

Multi-step reaction with 7 steps
1.1: chromium(VI) oxide; pyridine; acetic anhydride / dichloromethane / 0.42 h / Cooling with ice
2.1: sodium tetrahydroborate; ethanol / Cooling with ice
3.1: periodic acid / ethyl acetate / 2 h
4.1: sodium tetrahydroborate; ethanol / 3 h / Cooling with ice
5.1: acetic acid / 3 h / 80 °C
5.2: 18 h / Cooling with ice
6.1: pyridine / 3 h / 80 °C / Cooling with ice; Inert atmosphere
7.1: sulfuric acid; acetic acid / 10 h / -5 °C / Inert atmosphere
View Scheme

Multi-step reaction with 8 steps
1.1: chromium(VI) oxide; pyridine; acetic anhydride / dichloromethane / 0.42 h / Cooling with ice
2.1: sodium tetrahydroborate; ethanol / Cooling with ice
3.1: sulfuric acid / methanol
4.1: sodium periodate / ethanol; water / 4 h
5.1: sodium tetrahydroborate; ethanol / 3 h / Cooling with ice
6.1: acetic acid / 3 h / 80 °C
6.2: 18 h / Cooling with ice
7.1: pyridine / 3 h / 80 °C / Cooling with ice; Inert atmosphere
8.1: sulfuric acid; acetic acid / 10 h / -5 °C / Inert atmosphere
View Scheme

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

: 7408-41-5
2,3,5-tri-O-benzoyl-β-D-ribofuranosyl azide

Conditions

Conditions	Yield
With trimethylsilylazide; tin(IV) chloride In dichloromethane for 12h; Ambient temperature;	100%
With aluminum (III) chloride; trimethylsilylazide	99%
With trimethylsilyl trifluoromethanesulfonate; trimethylsilylazide In dichloromethane	98.5%

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

: 7677-24-9
trimethylsilyl cyanide

: 23316-67-8
2,3,5-tri-O-benzoyl-β-D-ribofuranosyl-1-carbonitrile

Conditions

Conditions	Yield
With tin(IV) chloride	100%
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 20℃; stereoselective reaction;	100%
With boron trifluoride diethyl etherate In nitromethane Ambient temperature;	87%

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

: 165546-13-4
6-(imidazol-1-yl)purine

: 9-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-6-(imidazol-1-yl)purine

Conditions

Conditions	Yield
With tin(IV) chloride In acetonitrile at 20℃; for 4h;	100%
With tin(IV) chloride In acetonitrile at 20℃; for 4h;	100%

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

: 55018-48-9, 55057-27-7, 101914-56-1, 102130-48-3, 107657-22-7
2,3,5-tri-O-benzoyl-1-deoxy-D-ribofuranose

Conditions

Conditions	Yield
With triethylsilane; trimethylsilyl trifluoromethanesulfonate In acetonitrile at 20℃; Inert atmosphere;	100%

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

: 100-51-6
benzyl alcohol

: 59556-69-3
2,3,5-tri-O-benzoyl-1-O-benzyl-β-D-ribofuranose

Conditions

Conditions	Yield
With tin(IV) chloride In dichloromethane at 0 - 20℃;	100%

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

: 75-89-8
2,2,2-trifluoroethanol

: 2,3,5-tri-O-benzoyl-1-O-(2,2,2-trifluoroethyl)-β-D-ribofuranose

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -30℃; for 1.5h;	100%

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

: 64-17-5
ethanol

: 52783-88-7
2,3,5-O-tribenzoyl-1-O-ethyl-β-D-ribofuranose

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -30℃; for 1.5h;	100%

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

: 5522-55-4
1,3-15N2-uracil

: 1,3-15N2-2’,3’,5’-O-benzoyl uridine

Conditions

Conditions	Yield
Stage #1: 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose; 1,3-15N2-uracil With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile at 20 - 60℃; for 0.5h; Inert atmosphere; Stage #2: With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 60℃; for 0.5h; Inert atmosphere;	100%

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

: 78103-44-3
5-morpholin-4-yl-2,4-bis-trimethylsilanyloxy-pyrimidine

: 58581-73-0
5-morpholinouridine 2',3',5'-tri-O-benzoate

Conditions

Conditions	Yield
trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane at 24℃; for 24h;	99%
With tin(IV) chloride In acetonitrile

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

: 5151-34-8
2,4-Dimethoxy-5-methylpyrimidine

: 7323-83-3
4-methoxy-5-methyl-1-(tri-O-benzoyl-β-D-ribofuranosyl)-1H-pyrimidin-2-one

Conditions

Conditions	Yield
With tin(IV) chloride In acetonitrile Ambient temperature;	99%

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

: 120268-57-7
5-Hexyl-2,4-dimethoxy-pyrimidine

: 120268-62-4
C37H38N2O9

Conditions

Conditions	Yield
With tin(IV) chloride In acetonitrile Ambient temperature;	99%

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

: 52522-97-1
5-nitro-2,4-bis-trimethylsilanyloxy-pyrimidine

: 23392-16-7
5-nitrouridine 2',3',5'-tri-O-benzoate

Conditions

Conditions	Yield
With 2,6-di-tert-butyl-4-methylpyridinium trifluoromethanesulfonate In acetonitrile at 120℃; for 0.00833333h; silyl-Hilbert-Johnson reaction; tubing reactor;	99%
trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane at 24℃; for 2h;	93%
With 2-methyl-5-phenylbenzoxazolium perchlorate In acetone for 6h; Vorbrueggen Nucleoside Synthesis; Reflux; Inert atmosphere; Schlenk technique;	153 mg

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

: 7288-28-0
2,4-bis(trimethylsiloxy)-5-methylpyrimidine

: 3180-76-5
2',3',5'-tri-O-benzoyluridine

Conditions

Conditions	Yield
With 2,6-di-tert-butyl-4-methylpyridinium trifluoromethanesulfonate In acetonitrile at 150℃; for 0.05h; silyl-Hilbert-Johnson reaction; Microwave irradiation;	99%
With tin(IV) chloride In 1,2-dichloro-ethane for 20h; Ambient temperature;	95%
With tin(IV) chloride In 1,2-dichloro-ethane at 20℃; for 48h;	93%

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

: 1070982-29-4
C15H27N5OSi2

: N6-isobutyryl-9-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)adenine

Conditions

Conditions	Yield
With 2,6-di-tert-butyl-4-methylpyridinium trifluoromethanesulfonate In acetonitrile at 150℃; for 0.05h; silyl-Hilbert-Johnson reaction; Microwave irradiation;	99%

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

: 38953-72-9
5-iodo-2,4-bis-O-trimethylsilyluracil

: 38953-75-2, 2880-91-3
(2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(5-iodo-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl dibenzoate

Conditions

Conditions	Yield
With 2,6-di-tert-butyl-4-methylpyridinium trifluoromethanesulfonate In acetonitrile at 120℃; for 0.0166667h; silyl-Hilbert-Johnson reaction; Microwave irradiation;	99%
With 2-methyl-5-phenylbenzoxazolium perchlorate In acetone for 6h; Vorbrueggen Nucleoside Synthesis; Reflux; Inert atmosphere; Schlenk technique;	193 mg
With poly(4,5-diphenyl-2-vinyloxazolium perchlorate) In acetonitrile for 6h; Vorbrueggen Nucleoside Synthesis; Schlenk technique; Inert atmosphere; Reflux;	194 mg

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

: 7057-43-4
5-trifluoromethyl-2,4-bis(trimethylsilyloxy)pyrimidine

: 2',3',5'-tri-O-benzoyl-5-(trifluoromethyl)uridine

Conditions

Conditions	Yield
With 2,6-di-tert-butyl-4-methylpyridinium trifluoromethanesulfonate In acetonitrile at 120℃; for 0.0166667h; silyl-Hilbert-Johnson reaction; Microwave irradiation;	99%
With 2-methyl-5-phenylbenzoxazolium perchlorate In acetone for 6h; Vorbrueggen Nucleoside Synthesis; Reflux; Inert atmosphere; Schlenk technique;	173 mg
With poly(4,5-diphenyl-2-vinyloxazolium perchlorate) In acetonitrile for 6h; Vorbrueggen Nucleoside Synthesis; Schlenk technique; Inert atmosphere; Reflux;	183 mg

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

: 79607-23-1, 122794-99-4
ethyl 6-bromo-4-oxo-1,4-dihydro-quinoline-3-carboxylate

: 224175-70-6
ethyl 6-bromo-1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-4-quinolone-3-carboxylate

Conditions

Conditions	Yield
Stage #1: 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose; ethyl 6-bromo-4-oxo-1,4-dihydro-quinoline-3-carboxylate With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile at 80℃; for 0.5h; Vorbrueggen Nucleoside Synthesis; Inert atmosphere; Stage #2: With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 80℃; for 3h; Inert atmosphere;	99%
Stage #1: ethyl 6-bromo-4-oxo-1,4-dihydro-quinoline-3-carboxylate With chloro-trimethyl-silane; N,O-Bis(trimethylsilyl)trifluoroacetamide In acetonitrile at 60 - 70℃; Stage #2: 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose With trimethylsilyl trifluoromethanesulfonate Stage #3: With sodium hydrogencarbonate In water

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

: 5451-40-1
2,6 dichloropurine

: 15373-23-6
(2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(2,6-dichloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl dibenzoate

Conditions

Conditions	Yield
Stage #1: 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose; 2,6 dichloropurine With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile at 60℃; for 0.5h; Stage #2: With titanium tetrachloride In dichloromethane; acetonitrile at -30 - 65℃; for 0.333333h;	98.8%
microwave irradiation;	37%
With tin(IV) chloride In acetonitrile at 20℃;
In ethanol at 100℃;	28 g
at 100℃;	28 g

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

: 4648-54-8
trimethylsilylazide

: 7408-41-5
2,3,5-tri-O-benzoyl-β-D-ribofuranosyl azide

Conditions

Conditions	Yield
With aluminium trichloride In dichloromethane at 0℃; for 0.166667h;	98%
With tin(IV) chloride	88%

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

: 18037-10-0
2,4-O,N-bis(trimethylsilyl)cytosine

: 31652-74-1
2',3',5'-tri-O-benzoyl-L-cytidine

Conditions

Conditions	Yield
trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane; benzene for 1h; Heating;	98%

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

: 57041-87-9
3-chloro-6-trimethylsilanyloxy-pyridazine

: 5116-33-6
3-chloro-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyridazin-6-one

Conditions

Conditions	Yield
With tin(IV) chloride In 1,2-dichloro-ethane 1.)45 deg C 2.)r.t., 1.5 h;	98%

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

: 66-22-8
uracil

: 58-96-8
uridine

Conditions

Conditions	Yield
With chloro-trimethyl-silane; trimethylsilyl trifluoromethanesulfonate; 1,1,1,3,3,3-hexamethyl-disilazane In acetonitrile Substitution;	98%

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

: 71-23-8
propan-1-ol

: 2,3,5-O-tribenzoyl-1-O-propyl-β-D-ribofuranose

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -30℃; for 0.5h;	98%

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

: 78-83-1
2-methyl-propan-1-ol

: 2,3,5-O-tribenzoyl-1-O-(2-methylpropyl)-β-D-ribofuranose

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -30℃; for 2.5h;	98%

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

: 5-D-6-13C-uracil

: C29(13)CH23(2)HN2O9

Conditions

Conditions	Yield
With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate In acetonitrile at 60℃; for 1h;	98%

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

: 1016-58-6
6-nitroveratryl alcohol

: 851597-72-3
4,5-dimethoxy-2-nitrobenzyl 2,3,5-tri-O-benzoyl-β-D-ribofuranoside

Conditions

Conditions	Yield
With tin(IV) chloride In dichloromethane at 0 - 20℃;	96%

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

: 120268-56-6
2,4-Dimethoxy-5-pentyl-pyrimidine

: 120268-61-3
C36H36N2O9

Conditions

Conditions	Yield
With tin(IV) chloride In acetonitrile Ambient temperature;	95%

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

2-chloro-4-methylbenzimidazole N-trimethylsilyl derivative: 2-chloro-4-methylbenzimidazole N-trimethylsilyl derivative

: 2-chloro-4-methyl-1-[β-D-erythro-pentofuranosyl]-1H-benzimidazole

Conditions

Conditions	Yield
Stage #1: 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose; 2-chloro-4-methylbenzimidazole N-trimethylsilyl derivative With tin(IV) chloride In acetonitrile at 15℃; for 3h; Stage #2: With ammonia In methanol	95%

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

: 4212-49-1
5-ethyluracil

: 25692-02-8
2',3',5'-tri-O-benzoyl-5-ethyluridine

Conditions

Conditions	Yield
Stage #1: 5-ethyluracil With bis-(trimethylsilyl)acetamide In acetonitrile at 60℃; for 4h; Stage #2: 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 60℃; for 4h;	95%

1-O-Acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose Specification

The 1-O-Acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose, with the CAS registry number 6974-32-9, is also known as beta-D-Ribofuranose, 1-acetate 2,3,5-tribenzoate. It belongs to the product categories of Pharmaceutical Intermediates; Sugars, Carbohydrates & Glucosides; Chiral; Carbohydrates; (intermediate of clofarabine); Biochemistry; Nucleosides, Nucleotides & Related Reagents; O-Substituted Sugars; Ribose; Riboses and 2'-Deoxyriboses; Sugars; Nucleic acids; Carbohydrates & Derivatives. Its EINECS registry number is 230-220-4. This chemical's molecular formula is C₂₈H₂₄O₉ and molecular weight is 504.48. Its IUPAC name is called [(2R,3R,4R,5S)-5-acetyloxy-3,4-dibenzoyloxyoxolan-2-yl]methyl benzoate. This chemical can be used as pharmaceutical intermediates.

Physical properties of 1-O-Acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose: (1)ACD/LogP: 3.18; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 3.18; (4)ACD/LogD (pH 7.4): 3.18; (5)ACD/BCF (pH 5.5): 154.86; (6)ACD/BCF (pH 7.4): 154.86; (7)ACD/KOC (pH 5.5): 1285.78; (8)ACD/KOC (pH 7.4): 1285.78; (9)#H bond acceptors: 9; (10)#Freely Rotating Bonds: 12; (11)Index of Refraction: 1.61; (12)Molar Refractivity: 129.52 cm³; (13)Molar Volume: 373.4 cm³; (14)Surface Tension: 59.4 dyne/cm; (15)Density: 1.35 g/cm³; (16)Flash Point: 264.3 °C; (17)Enthalpy of Vaporization: 92.02 kJ/mol; (18)Boiling Point: 621 °C at 760 mmHg; (19)Vapour Pressure: 2.41E-15 mmHg at 25°C.

Preparation: this chemical can be prepared by acetic acid anhydride and methyl 2,3,5-tri-O-benzoyl-a-L-arabinofuranoside. This reaction will need reagent H₂SO₄ conc. and solvent acetic acid. The reaction time is 4 hours. The yield is about 95%.

Uses of 1-O-Acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose: it can be used to produce 5-methyl-1-(tri-O-benzoyl-a-L-arabinofuranosyl)-1H-pyrimidine-2,4-dione by heating. This reaction will need reagent Me₃SiNHSiMe₃, Me₃SiCl, SnCl₄ and solvent acetonitrile with reaction time of 1 hour. The yield is about 60%.

When you are using this chemical, please be cautious about it as the following:
This chemical may cause inflammation to the skin or other mucous membranes. It is irritating to eyes and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing and eye/face protection.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O[C@@H]3O[C@@H]([C@@H](OC(=O)c1ccccc1)[C@H]3OC(=O)c2ccccc2)COC(=O)c4ccccc4)C
(2)InChI: InChI=1/C28H24O9/c1-18(29)34-28-24(37-27(32)21-15-9-4-10-16-21)23(36-26(31)20-13-7-3-8-14-20)22(35-28)17-33-25(30)19-11-5-2-6-12-19/h2-16,22-24,28H,17H2,1H3/t22-,23-,24-,28-/m1/s1
(3)InChIKey: GCZABPLTDYVJMP-CBUXHAPBBG

Product Name

beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate

Synthetic route

1-O-Acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose Specification

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