beta-D-Ribofuranose1,2,3,5-tetraacetate supplier

Name
beta-D-Ribofuranose 1,2,3,5-tetraacetate
EINECS 235-898-5
CAS No. 13035-61-5
Article Data54
CAS DataBase
Density 1.29 g/cm³
Solubility
Melting Point 81-83 °C(lit.)
Formula C₁₃H₁₈O₉
Boiling Point 385.6 °C at 760 mmHg
Molecular Weight 318.281
Flash Point 168.5 °C
Transport Information
Appearance white to almost white crystalline powder
Safety 22-24/25
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Ribofuranose,tetraacetate, β-D- (8CI);β-D-Ribofuranose, tetraacetate (9CI);1,2,3,5-Tetra-O-acetyl-β-D-ribofuranose;1,2,3,5-Tetra-O-acetyl-β-D-ribose;1,2,3,5-Tetraacetyl-β-D-ribofuranose;1β-D-Tetraacetylribose;NSC 18738;Tetra-O-acetyl-β-D-ribofuranose;Tetraacetyl-β-D-ribofuranose;Tetraacetylribofuranose;
PSA 114.43000
LogP -0.29910

Synthetic route

: 108-24-7
acetic anhydride

: 118-00-3
G

A: 3056-33-5
2,9-diacetylguanine

B: 13035-61-5
1,2,3,5-tetraacetylribose

Conditions

Conditions	Yield
Stage #1: acetic anhydride; G at 136℃; for 1h; Stage #2: With trifluoroacetic acid at 60 - 100℃;	A 96% B 86%

...Expand

: 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

: 108-24-7
acetic anhydride

: 13035-61-5
1,2,3,5-tetraacetylribose

Conditions

Conditions	Yield
With pyridine for 24h;	95%
With sodium acetate for 5h; Reflux;

: 103-84-4
Acetanilid

: 58-63-9
inosine

: 13035-61-5
1,2,3,5-tetraacetylribose

Conditions

Conditions	Yield
With aluminum (III) chloride In methanol at 60℃; for 2h; Solvent; Temperature;	95%

: 54548-46-8
(2R,3R,4R,5R)-4-(acetyloxty)-2-[(acetyloxy)methyl]-5-(1H-1,2,3-benzotriazol-1-yl)tetrahydro-3-furanyl acetate

A: 95-14-7
1,2,3-Benzotriazole

B: 13035-61-5
1,2,3,5-tetraacetylribose

Conditions

Conditions	Yield
With acetic anhydride; trifluoroacetic acid at 95℃;	A n/a B 94.3%

: 28708-32-9
1,2,3,5-tetra-O-acetyl-D-ribofuranose

A: 119240-35-6
1,2,3-tri-O-acetyl-α-D-ribofuranoside

B: 13035-61-5
1,2,3,5-tetraacetylribose

Conditions

Conditions	Yield
With Lipozyme TL IM In di-isopropyl ether; butan-1-ol at 40 - 42℃; for 12h; Enzymatic reaction; regioselective reaction;	A 92% B n/a

: 108-24-7
acetic anhydride

: 58-63-9
Inosine

A: 408531-05-5
C7H6N4O2

B: 13035-61-5
1,2,3,5-tetraacetylribose

Conditions

Conditions	Yield
Stage #1: acetic anhydride; Inosine at 136℃; Stage #2: With trifluoroacetic acid at 60 - 100℃;	A n/a B 90%

...Expand

: 86357-13-3
2-(acetoxymethoxy)-1,3-propanediyl diacetate

: 9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-N2-acetylguanine

A: 86357-17-7
7-(1,3-diacetoxy-2-propoxymethyl)-N2-acetylguanine

B: 86357-14-4
9-(1,3-diacetoxy-2-propoxymethyl)-N2-acetylguanine

C: 13035-61-5
1,2,3,5-tetraacetylribose

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In chlorobenzene for 2h; Heating;	A 38% B 53% C 85%

...Expand

: 108-24-7
acetic anhydride

: 58-61-7
adenosine

A: 10527-91-0
9-acetyl-6-acetylamino-9H-purine

B: 13035-61-5
1,2,3,5-tetraacetylribose

Conditions

Conditions	Yield
Stage #1: acetic anhydride; adenosine at 136℃; Stage #2: With trifluoroacetic acid at 60 - 100℃;	A n/a B 84%

...Expand

: 52554-28-6
methyl 2,3,5-tri-O-acetyl-D-ribofuranoside

: 108-24-7
acetic anhydride

A: 13035-61-5
1,2,3,5-tetraacetylribose

B: 50730-26-2
tetra-O-acetyl-D-ribofuranose

Conditions

Conditions	Yield
With sulfuric acid In acetic acid	A 45% B n/a

...Expand

: 37077-80-8
2,3,5-tri-O-acetyl-1-O-methyl-β-D-ribofuranose

: 108-24-7
acetic anhydride

: 13035-61-5
1,2,3,5-tetraacetylribose

Conditions

Conditions	Yield
With sulfuric acid; acetic acid at 20℃; for 3h;	43%
With sulfuric acid; acetic acid	43%
With sulfuric acid; acetic acid

: 94482-37-8
5-O-triphenylmethyl-D-ribofuranose-1,2,3-triacetate

: 506-96-7
Acetyl bromide

: 108-24-7
acetic anhydride

: 13035-61-5
1,2,3,5-tetraacetylribose

...Expand

: 110-86-1
pyridine

: 50-69-1
D-ribose

: 108-24-7
acetic anhydride

A: 13035-61-5
1,2,3,5-tetraacetylribose

B: 50730-26-2
tetra-O-acetyl-D-ribofuranose

C: 4257-95-8
1,2,3,4-tri-O-acetyl-α-D-ribopyranose

D: 4627-30-9
1,2,3,4-tetra-O-acetyl-β-D-ribopyranose

...Expand

: 50-69-1
D-ribose

: 13035-61-5
1,2,3,5-tetraacetylribose

Conditions

Conditions	Yield
With sulfuric acid anschl. mit Acetanhydrid und Essigsaeure unter Zusatz von H2SO4;
With sulfuric acid anschl. mit Acetanhydrid und Pyridin, Beh. des Rktprod. mit Essigsaeure, Acetanhydrid und H2SO4;
With hydrogenchloride; methanol anschl. mit Acetanhydrid und Pyridin, Beh. des Rktprod. mit HBr in Essigsaeure, anschl. Beh. des isolierten Rktprod. mit Acetanhydrid und Pyridin;
Multi-step reaction with 3 steps 1: Acidic conditions 2: pyridine 3: acetic acid; sulfuric acid View Scheme

: 50-69-1
D-ribose

: 127-09-3
sodium acetate

: 108-24-7
acetic anhydride

A: 13035-61-5
1,2,3,5-tetraacetylribose

B: 50730-26-2
tetra-O-acetyl-D-ribofuranose

C: 4257-95-8
1,2,3,4-tri-O-acetyl-α-D-ribopyranose

D: 4627-30-9
1,2,3,4-tetra-O-acetyl-β-D-ribopyranose

...Expand

: 50-69-1
D-ribose

: 108-24-7
acetic anhydride

: 13035-61-5
1,2,3,5-tetraacetylribose

Conditions

Conditions	Yield
With pyridine

: 50-69-1
D-ribose

: 108-24-7
acetic anhydride

A: 13035-61-5
1,2,3,5-tetraacetylribose

B: 4627-30-9
1,2,3,4-tetra-O-acetyl-β-D-ribopyranose

Conditions

Conditions	Yield
With sodium acetate

...Expand

: 108-24-7
acetic anhydride

: 130792-81-3
(2S,3R,4R,5R)-5-(hydroxymethyl)tetrahydrofuran-2,3,4-triyl triacetate

: 13035-61-5
1,2,3,5-tetraacetylribose

Conditions

Conditions	Yield
With pyridine

: 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

: 108-24-7
acetic anhydride

A: 13035-61-5
1,2,3,5-tetraacetylribose

B: 50730-26-2
tetra-O-acetyl-D-ribofuranose

C: 4257-95-8
1,2,3,4-tri-O-acetyl-α-D-ribopyranose

D: 4627-30-9
1,2,3,4-tetra-O-acetyl-β-D-ribopyranose

Conditions

Conditions	Yield
With H-Beta zeolite for 2h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

...Expand

: 50-69-1
D-ribose

: 108-24-7
acetic anhydride

A: 13035-61-5
1,2,3,5-tetraacetylribose

B tetra-O-acetyl-β-ribopyranose: tetra-O-acetyl-β-ribopyranose

Conditions

Conditions	Yield
With pyridine

...Expand

: 10257-32-6
D-ribose

: 108-24-7
acetic anhydride

A: 13035-61-5
1,2,3,5-tetraacetylribose

B: 50730-26-2
tetra-O-acetyl-D-ribofuranose

C: 4257-95-8
1,2,3,4-tri-O-acetyl-α-D-ribopyranose

D: 4627-30-9
1,2,3,4-tetra-O-acetyl-β-D-ribopyranose

Conditions

Conditions	Yield
Stage #1: D-ribose With ammonium chloride; ammonia In methanol at 0℃; for 0.5h; Stage #2: acetic anhydride In pyridine at 20℃; for 12h; Title compound not separated from byproducts;
With sulfuric acid In acetic acid at 50℃; for 3h; Acetylation; Further byproducts. Title compound not separated from byproducts.;
Stage #1: D-ribose With boric acid In acetic acid at 50℃; for 1h; Cyclization; Stage #2: acetic anhydride With sulfuric acid In acetic acid at 50℃; for 3h; Acetylation; Further stages. Further byproducts. Title compound not separated from byproducts.;

...Expand

: 94482-37-8
5-O-triphenylmethyl-D-ribofuranose-1,2,3-triacetate

: 13035-61-5
1,2,3,5-tetraacetylribose

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: water; acetic acid 2: pyridine View Scheme

: 36468-53-8
β-D-ribofuranose

: 108-24-7
acetic anhydride

A: 13035-61-5
1,2,3,5-tetraacetylribose

B: 50730-26-2
tetra-O-acetyl-D-ribofuranose

Conditions

Conditions	Yield
With perchloric acid In water at -70 - 20℃;

...Expand

: 108-05-4
vinyl acetate

: 50-69-1
D-ribose

A: 13035-61-5
1,2,3,5-tetraacetylribose

B: 50730-26-2
tetra-O-acetyl-D-ribofuranose

Conditions

Conditions	Yield
With sodium carbonate In water at 20℃; for 0.666667h; pH=9;

...Expand

: 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

A: 13035-61-5
1,2,3,5-tetraacetylribose

B: 50730-26-2
tetra-O-acetyl-D-ribofuranose

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Candida antarctica lipase B / tetrahydrofuran / 55 °C / Enzymatic reaction 2: pyridine / 20 °C View Scheme

: 108-24-7
acetic anhydride

: 146572-26-1, 146572-27-2, 146572-32-9, 146572-33-0
Acetic acid (2R,3S,4R)-3,4,5-trihydroxy-tetrahydro-furan-2-ylmethyl ester

A: 13035-61-5
1,2,3,5-tetraacetylribose

B: 50730-26-2
tetra-O-acetyl-D-ribofuranose

Conditions

Conditions	Yield
With pyridine at 20℃; optical yield given as %de;

...Expand

: 108-05-4
vinyl acetate

: 36468-53-8
β-D-ribofuranose

: 13035-61-5
1,2,3,5-tetraacetylribose

Conditions

Conditions	Yield
at 20℃; pH=12; aq. phosphate buffer;

: 36468-53-8
β-D-ribofuranose

: 108-24-7
acetic anhydride

: 13035-61-5
1,2,3,5-tetraacetylribose

Conditions

Conditions	Yield
With iron(III) chloride at 25℃; for 0.25h; Sonication;
With iron(III) chloride at 25℃; for 0.25h; Sonication;

: 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

: 108-24-7
acetic anhydride

A: 13035-61-5
1,2,3,5-tetraacetylribose

B: 4627-30-9
1,2,3,4-tetra-O-acetyl-β-D-ribopyranose

Conditions

Conditions	Yield
In neat (no solvent) at 80℃; for 24h; Molecular sieve; Overall yield = 61 %;

...Expand

: 36468-53-8
β-D-ribofuranose

: 13035-61-5
1,2,3,5-tetraacetylribose

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: Dowex-50W 2: pyridine 3: acetic acid; sulfuric acid View Scheme

: 13035-61-5
1,2,3,5-tetraacetylribose

: 53402-29-2
2,3,5-tri-O-acetyl-β-D-ribofuranosyl chloride

Conditions

Conditions	Yield
With thionyl chloride; acetic acid In dichloromethane for 18h; Ambient temperature;	100%
With hydrogenchloride In dichloromethane at 0℃; for 2.5h;
With methanol; acetyl chloride In dichloromethane at 20℃; for 72h;

: 13035-61-5
1,2,3,5-tetraacetylribose

: 70964-85-1
1-azido-2,3,4-tri-O-acetylribose

Conditions

Conditions	Yield
With trimethylsilylazide; tin(IV) chloride In dichloromethane at 20℃;	100%
With trimethylsilylazide; tin(IV) chloride In dichloromethane at 20℃; stereoselective reaction;	100%
With trimethylsilylazide; tin(IV) chloride In dichloromethane for 48h; Ambient temperature;	98%

: 27607-77-8
trimethylsilyl trifluoromethanesulfonate

: 98-92-0
nicotinamide

: 13035-61-5
1,2,3,5-tetraacetylribose

: 3-carbamoyl-1-((2R,3R,4R,5R)-3,4-diacetoxy-5-(acetoxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium trifluoromethanesulfonate

Conditions

Conditions	Yield
Stage #1: nicotinamide; 1,2,3,5-tetraacetylribose In acetonitrile at 20℃; Stage #2: trimethylsilyl trifluoromethanesulfonate In acetonitrile for 0.333333h;	100%
Stage #1: nicotinamide; 1,2,3,5-tetraacetylribose With chloro-trimethyl-silane; 1,1,1,3,3,3-hexamethyl-disilazane In acetonitrile Stage #2: trimethylsilyl trifluoromethanesulfonate In acetonitrile at 20℃; Reagent/catalyst;
Stage #1: trimethylsilyl trifluoromethanesulfonate; nicotinamide In acetonitrile for 0.0833333h; Stage #2: 1,2,3,5-tetraacetylribose In acetonitrile at 20℃; for 0.5h; Inert atmosphere;
In acetonitrile at -5℃; for 8h; Inert atmosphere;	19 g

...Expand

: 27607-77-8
trimethylsilyl trifluoromethanesulfonate

: 1079394-06-1
N-(trimethylsilyl)pyridine-3-carboxamide

: 13035-61-5
1,2,3,5-tetraacetylribose

: 3-carbamoyl-1-((2R,3R,4R,5R)-3,4-diacetoxy-5-(acetoxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium trifluoromethanesulfonate

Conditions

Conditions	Yield
In dichloromethane for 0.5h; Milling;	100%
for 0.5h; Milling;

...Expand

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

: 13035-61-5
1,2,3,5-tetraacetylribose

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

Conditions

Conditions	Yield
Stage #1: ethyl 6-bromo-4-oxo-1,4-dihydro-quinoline-3-carboxylate; 1,2,3,5-tetraacetylribose 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%

: 7677-24-9
trimethylsilyl cyanide

: 13035-61-5
1,2,3,5-tetraacetylribose

: 82225-19-2
2,3,5-tri-O-acetyl-β-D-ribofuranosyl cyanide

Conditions

Conditions	Yield
With tin(IV) chloride In dichloromethane for 4h; Ambient temperature;	98%
With tin(IV) chloride In dichloromethane at 20℃; for 30h; Reflux;

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

: 13035-61-5
1,2,3,5-tetraacetylribose

: 84500-33-4, 65499-40-3
2',3',5'-tri-O-acetyl-5-iodouridine

Conditions

Conditions	Yield
With 2-methyl-5-phenylbenzoxazolium perchlorate In acetonitrile for 7h; Reflux;	98%
With 2-methyl-5-phenylbenzoxazolium perchlorate In acetonitrile for 7h; Vorbrueggen Nucleoside Synthesis; Reflux; Inert atmosphere; Schlenk technique;	1.71 g
With poly(4,5-diphenyl-2-vinyloxazolium perchlorate) In acetonitrile for 7h; Vorbrueggen Nucleoside Synthesis; Schlenk technique; Inert atmosphere; Reflux;	143 mg

: 6320-03-2
2-chlorothiphenol

: 13035-61-5
1,2,3,5-tetraacetylribose

: 2-chlorophenyl 2,3,5-tetra-O-acetyl-1-thio-β-D-ribofuranoside

Conditions

Conditions	Yield
With indium(III) bromide In dichloromethane at 20℃; for 2h; stereoselective reaction;	98%

: 371-42-6
4-Fluorothiophenol

: 13035-61-5
1,2,3,5-tetraacetylribose

: 4-fluorobenzene 2,3,5-tetra-O-acetyl-1-thio-β-D-ribofuranoside

Conditions

Conditions	Yield
With indium(III) bromide In dichloromethane at 20℃; for 2h; stereoselective reaction;	98%

: 5451-40-1
2,6-dichloro-7H-purine

: 13035-61-5
1,2,3,5-tetraacetylribose

: 3056-18-6
(2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(2,6-dichloro-9H-purin-9-yl)tetrahydro-3-furanyl acetate

Conditions

Conditions	Yield
With dmap In toluene at 100℃; for 2h; Reagent/catalyst;	97.5%

: 4551-15-9
phenylthiotrimethylsilane

: 13035-61-5
1,2,3,5-tetraacetylribose

: 52544-88-4
phenyl 2,3,5-tri-O-acetyl-1-thio-β-D-ribofuranoside

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane	97%

: 645-96-5
Benzeneselenol

: 13035-61-5
1,2,3,5-tetraacetylribose

: 74458-63-2
phenyl 2,3,5-tri-O-acetyl-1-seleno-β-D-ribofuranoside

Conditions

Conditions	Yield
With indium(III) bromide In dichloromethane at 20℃; for 2h; stereoselective reaction;	97%
With boron trifluoride diethyl etherate	92%

: 108-98-5
thiophenol

: 13035-61-5
1,2,3,5-tetraacetylribose

: 52544-88-4
phenyl 2,3,5-tri-O-acetyl-1-thio-β-D-ribofuranoside

Conditions

Conditions	Yield
With iodine; iron In dichloromethane at 20℃; for 1h; Inert atmosphere; diastereoselective reaction;	97%
With molybdenium(VI) dioxodichloride In dichloromethane at 20℃; for 14h;	86%

: 106-45-6
para-thiocresol

: 13035-61-5
1,2,3,5-tetraacetylribose

: 817197-67-4
(2R,5S)-2-(acetoxymethyl)-5-(p-tolylthio)tetrahydrofuran-3,4-diyl diacetate

Conditions

Conditions	Yield
With indium(III) bromide In dichloromethane at 20℃; for 2h; stereoselective reaction;	97%
With boron trifluoride diethyl etherate In dichloromethane at -78 - 0℃; Inert atmosphere;	96%
With tin(IV) chloride In dichloromethane at 0 - 20℃; for 4h;

: 7677-24-9
trimethylsilyl cyanide

: 13035-61-5
1,2,3,5-tetraacetylribose

: 82372-97-2
3,5-di-O-acetyl-1,2-O-(1-endo-cyanoethylidene)-α-D-ribofuranose

Conditions

Conditions	Yield
tin(ll) chloride Ambient temperature;	96%
tin(ll) chloride for 2h; Ambient temperature;	96%

: 13035-61-5
1,2,3,5-tetraacetylribose

: 39110-68-4
2,3,5-tri-O-acetyl-D-ribofuranosyl bromide

Conditions

Conditions	Yield
With trimethylsilyl bromide In dichloromethane at -40 - 20℃;	96%
With hydrogen bromide In dichloromethane at -20℃; for 3h;
With trimethylsilyl bromide In chloroform at 0℃;
With hydrogen bromide; acetic acid In dichloromethane at 0℃; for 0.333333h;

: 27607-77-8
trimethylsilyl trifluoromethanesulfonate

: 13035-61-5
1,2,3,5-tetraacetylribose

: 69688-12-6
N,N-bis(trimethylsilyl)nicotinamide

: 3-carbamoyl-1-((2R,3R,4R,5R)-3,4-diacetoxy-5-(acetoxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium trifluoromethanesulfonate

Conditions

Conditions	Yield
In 1,2-dichloro-ethane at 45℃; for 2h;	96%
In 1,2-dichloro-ethane at 45℃; for 2h; Inert atmosphere;	144 mg

...Expand

: 21873-50-7
6-fluoroquinolin-4(1H)-one

: 13035-61-5
1,2,3,5-tetraacetylribose

: 6-fluoro-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)quinolin-4(1H)-one

Conditions

Conditions	Yield
Stage #1: 6-fluoroquinolin-4(1H)-one; 1,2,3,5-tetraacetylribose With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile at 80℃; for 0.25h; microwave irradiation; Stage #2: With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 80℃; for 0.833333h; microwave irradiation; Further stages.;	96%

: 10597-52-1
4-nitro-benzimidazole

: 13035-61-5
1,2,3,5-tetraacetylribose

: 89986-36-7
(2R,3R,4R,5R)-2-(acetoxymethyl)-5-(4-nitro-1H-benzo[d]imidazol-1-yl)tetrahydrofuran-3,4-diyl diacetate

Conditions

Conditions	Yield
With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate In acetonitrile for 3h; Reflux;	95%
With toluene-4-sulfonic acid at 160℃; under 25 Torr; for 0.333333h;	60%
With tin(IV) chloride In acetonitrile	37%

: 127211-14-7
2-Bromo-6-[2-(4-nitro-phenyl)-ethoxy]-9-trimethylsilanyl-9H-purine

: 13035-61-5
1,2,3,5-tetraacetylribose

A: Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-{2-bromo-6-[2-(4-nitro-phenyl)-ethoxy]-purin-7-yl}-tetrahydro-furan-3-yl ester

B: 127218-16-0
Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-{2-bromo-6-[2-(4-nitro-phenyl)-ethoxy]-purin-9-yl}-tetrahydro-furan-3-yl ester

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In acetonitrile reflux, 1h; rt, 16 h; Yields of byproduct given;	A n/a B 95%

...Expand

: 75-77-4
chloro-trimethyl-silane

: 13035-61-5
1,2,3,5-tetraacetylribose

: 490-59-5
isoalloxazine

: 259530-49-9
3-(2',3',5'-triacetyl-β-D-ribofuranosyl)benzo[g]pteridine-2,4-(1H,3H)-dione

Conditions

Conditions	Yield
Stage #1: chloro-trimethyl-silane; isoalloxazine With triethylamine In benzene at 20℃; for 48h; Substitution; Stage #2: 1,2,3,5-tetraacetylribose With tin(IV) chloride In dichloromethane at -20℃; for 0.25h; Substitution; Further stages.;	95%

...Expand

: 2302-30-9
4,5-dibromo-1H-imidazole

: 13035-61-5
1,2,3,5-tetraacetylribose

: 437614-21-6
4,5-dibromo-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazole

Conditions

Conditions	Yield
Stage #1: 4,5-dibromo-1H-imidazole With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile at 35℃; for 0.333333h; Stage #2: 1,2,3,5-tetraacetylribose With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 65℃; for 1.5h; Vorbruggen's reaction;	95%
Stage #1: 4,5-dibromo-1H-imidazole; 1,2,3,5-tetraacetylribose With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile at 20℃; for 5h; Stage #2: With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 0 - 60℃; for 8h; Further stages.;	66%
Stage #1: 4,5-dibromo-1H-imidazole; 1,2,3,5-tetraacetylribose With benzenesulfonamide In acetonitrile Stage #2: With trimethylsilyl trifluoromethanesulfonate Further stages.;

: 4928-88-5
methyl 1H-1,2,4-triazole-3-carboxylate

: 13035-61-5
1,2,3,5-tetraacetylribose

: 57198-04-6, 39925-10-5
1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-1,2,4-triazole-3-carboxylic acid methyl ester

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In methanol	95%
With toluene-4-sulfonic acid In ethanol	92%
With toluene-4-sulfonic acid In 2-methyl-propan-1-ol	92%

: 2,2,2-trifluoro-N-(7-chloro-5-methyl-3H-imidazo[4,5-b]pyridin-6-yl)acetamide

: 13035-61-5
1,2,3,5-tetraacetylribose

: 2,2,2-trifluoro-N-[7-chloro-5-methyl-3-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridin-6-yl]acetamide

Conditions

Conditions	Yield
Stage #1: 2,2,2-trifluoro-N-(7-chloro-5-methyl-3H-imidazo[4,5-b]pyridin-6-yl)acetamide With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile at 80℃; for 0.25h; Inert atmosphere; Stage #2: 1,2,3,5-tetraacetylribose With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 0℃; for 3h; Inert atmosphere; Reflux;	95%

: 6-chloro-2-((3,3,3-trifluoropropyl)thio)-9H-purine

: 13035-61-5
1,2,3,5-tetraacetylribose

: [(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-({6-chloro-2-[(3,3,3-trifluoropropyl)thio]-9H-purin-9-yl})tetrahydrofuran-2-yl]methyl acetate

Conditions

Conditions	Yield
Stage #1: 6-chloro-2-((3,3,3-trifluoropropyl)thio)-9H-purine; 1,2,3,5-tetraacetylribose In 1,2-dichloro-ethane for 0.5h; Reflux; Large scale; Stage #2: With tin(IV) chloride In 1,2-dichloro-ethane for 2h; Reagent/catalyst; Solvent; Temperature; Reflux; Large scale;	95%

: 13035-61-5
1,2,3,5-tetraacetylribose

: 106707-71-5
2,3,5-tri-O-acetyl-1,4-anhydro-D-ribitol

Conditions

Conditions	Yield
With triethylsilane; trimethylsilyl trifluoromethanesulfonate In acetonitrile for 24h; Ambient temperature;	94%
Multi-step reaction with 2 steps 1: trifluoroborane diethyl ether / dichloromethane / 2 h / 0 - 20 °C 2: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / toluene / 2.5 h / Reflux View Scheme

beta-D-Ribofuranose1,2,3,5-tetraacetate Specification

The beta-D-Ribofuranose1,2,3,5-tetraacetate, with the CAS registry number 13035-61-5 and EINECS registry number 235-898-5, has the systematic name of 1,2,3,5-tetra-O-acetyl-β-L-ribofuranose. It is a kind of white to almost white crystalline powder, and belongs to the following product categories: Pharmaceutical Intermediates; Sugars, Carbohydrates & Glucosides; Biochemistry; Nucleosides, Nucleotides & Related Reagents; O-Substituted Sugars; Ribose; Riboses and 2'-Deoxyriboses; Sugars; Nucleic acids. And the molecular formula of the chemical is C₁₃H₁₈O₉. Besides, it is always used as intermediates of ribavirin.

The physical properties of beta-D-Ribofuranose1,2,3,5-tetraacetate are as followings: (1)ACD/LogP: 0.82; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 9; (4)#H bond donors: 0; (5)#Freely Rotating Bonds: 9; (6)Polar Surface Area: 114.43 Å²; (7)Index of Refraction: 1.475; (8)Molar Refractivity: 69.27 cm³; (9)Molar Volume: 245.8 cm³; (10)Polarizability: 27.46×10^-24cm³; (11)Surface Tension: 44.5 dyne/cm; (12)Density: 1.29 g/cm³; (13)Flash Point: 168.5 °C; (14)Enthalpy of Vaporization: 63.45 kJ/mol; (15)Boiling Point: 385.6 °C at 760 mmHg; (16)Vapour Pressure: 3.76E-06 mmHg at 25°C.

You should be cautious while dealing with this chemical. It irritates to eyes, respiratory system and skin. Therefore, you had better take the following instructions: Do not breathe dust and then try to avoid contacting with skin and eyes.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O[C@H]1O[C@H]([C@H](OC(=O)C)[C@@H]1OC(=O)C)COC(=O)C)C
(2)InChI: InChI=1/C13H18O9/c1-6(14)18-5-10-11(19-7(2)15)12(20-8(3)16)13(22-10)21-9(4)17/h10-13H,5H2,1-4H3/t10-,11-,12-,13-/m0/s1
(3)InChIKey: IHNHAHWGVLXCCI-CYDGBPFRBE

Product Name

beta-D-Ribofuranose 1,2,3,5-tetraacetate

Synthetic route

beta-D-Ribofuranose1,2,3,5-tetraacetate Specification

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