Spongouridine supplier | CasNO.3083-77-0

Name
Spongouridine
EINECS 221-386-9
CAS No. 3083-77-0
Article Data64
CAS DataBase
Density 1.674 g/cm³
Solubility
Melting Point 220-222 °C
Formula C₉H₁₂N₂O₆
Boiling Point
Molecular Weight 244.204
Flash Point
Transport Information
Appearance white to off-white solid
Safety 22-24/25-36-26
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione;1-pentofuranosylpyrimidine-2,4(1H,3H)-dione;Ara-U;Arabinofuranosyluracil;Arabinosyluracil;Arauridine;Uracil arabinoside;Uracil b-D-arabinofuranoside;
PSA 124.78000
LogP -2.85190

Synthetic route

: 14057-18-2
1-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)uracil

: 3083-77-0
araU

Conditions

Conditions	Yield
With keratinase from Paecilomyces marquandii for 216h; pH=8; aq. phosphate buffer; Enzymatic reaction;	100%

: 147-94-4
arabinosyl cytosine

: 3083-77-0
araU

Conditions

Conditions	Yield
With cytidine deaminase enzyme In aq. phosphate buffer at 37℃; for 0.0833333h; pH=7; Enzymatic reaction;	99%
cytidine deaminase ( EC 3.5.4.5 ) at 37℃; for 48h; pH=6.8 with acetic acid;
With sodium hydroxide at 90.1℃; Rate constant; Mechanism; various reagent concentration, decomposition to nonchromophoric products;

: 3736-77-4
2,2'-Anhydrouridine

: 3083-77-0
araU

Conditions

Conditions	Yield
With trifluoroacetic acid In N,N-dimethyl-formamide at 80℃; for 10h;	95%
With trifluoroacetic acid In N,N-dimethyl-formamide at 80℃;	95%
Stage #1: 2,2'-Anhydrouridine With sodium hydroxide; water at 20℃; for 18 - 20h; Stage #2: With hydrogenchloride; water pH=~ 6.5;	88%

: 87186-13-8
2,2'-Anhydrouridine 3'-carbamate

: 3083-77-0
araU

Conditions

Conditions	Yield
With water; triethylamine at 60℃; for 48h;	90%

: 28309-53-7
2,2''-anhydro-1-(3'',5''-di-O-acetyl-β-D-arabinofuranosyl)uracil

: 3083-77-0
araU

Conditions

Conditions	Yield
With sodium hydroxide for 4h; Ambient temperature;	68%

: 847650-91-3
1-((2R,4S,5R)-3,4-anhydro-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-4(1H)-one

: 3083-77-0
araU

Conditions

Conditions	Yield
Stage #1: 1-((2R,4S,5R)-3,4-anhydro-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-4(1H)-one With hydrogenchloride; water at 80℃; for 2h; Stage #2: With sodium hydroxide pH=Ca. 7;	68%

: 58-96-8
uridine

: 3083-77-0
araU

Conditions

Conditions	Yield
With bis(phenyl) carbonate; copper; sodium hydrogencarbonate In N,N-dimethyl-formamide at 140 - 150℃; for 45h;	58.5%
Multi-step reaction with 2 steps 1: 80 percent / diphenyl carbonate; NaHCO3 / dimethylformamide / 1.67 h / 140 °C 2: 95 percent / TFA / dimethylformamide / 10 h / 80 °C View Scheme
Multi-step reaction with 2 steps 1: 79 percent / (C6H5O)2CO / dimethylformamide 2: 61 percent / LiOH View Scheme

: 28321-79-1
diiminosuccinonitrile

: 58-96-8
uridine

A: 3736-77-4
2,2'-Anhydrouridine

B: 3083-77-0
araU

C: 87186-13-8
2,2'-Anhydrouridine 3'-carbamate

D: 6195-72-8
1-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2-oxotetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-pyrimidine-2,4(1H,3H)-dione

Conditions

Conditions	Yield
With diiminosuccinonitrile; Imidazole-HCl buffer at 2℃; for 96h; Further byproducts given;	A 10% B n/a C 54% D 5%

...Expand

: C15H24N2O6

: 3083-77-0
araU

Conditions

Conditions	Yield
Stage #1: C15H24N2O6 With diethylamino-sulfur trifluoride In dichloromethane Stage #2: With hydrogenchloride In methanol; water	53%

: 506-68-3
bromocyane

: 58-96-8
uridine

A: 3736-77-4
2,2'-Anhydrouridine

B: 3083-77-0
araU

C: 87186-13-8
2,2'-Anhydrouridine 3'-carbamate

D: 89998-90-3
Uridine 3'-carbamate

Conditions

Conditions	Yield
With triethylamine In water at 2℃; for 0.75h; Further byproducts given;	A 4% B 13% C 37% D 27%

...Expand

: 506-68-3
bromocyane

: 58-96-8
uridine

A: 3736-77-4
2,2'-Anhydrouridine

B: 3083-77-0
araU

C: 87186-13-8
2,2'-Anhydrouridine 3'-carbamate

D: 89998-90-3
Uridine 3'-carbamate

E: 89998-91-4
2'-O-carbamoyluridine

F: 6195-72-8
1-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2-oxotetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-pyrimidine-2,4(1H,3H)-dione

Conditions

Conditions	Yield
With triethylamine In water at 2℃; for 0.75h; or with diiminosuccinonitrile;	A 2% B 13% C 37% D 27% E 2% F 4%

...Expand

: 506-68-3
bromocyane

: 58-96-8
uridine

A: 3083-77-0
araU

B: 87186-13-8
2,2'-Anhydrouridine 3'-carbamate

C: 89998-90-3
Uridine 3'-carbamate

D: 6195-72-8
1-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2-oxotetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-pyrimidine-2,4(1H,3H)-dione

Conditions

Conditions	Yield
With triethylamine In water at 2℃; for 0.75h; Further byproducts given;	A 13% B 37% C 27% D 4%

...Expand

: 58-96-8
uridine

A: 3083-77-0
araU

B: 87186-13-8
2,2'-Anhydrouridine 3'-carbamate

C: 89998-90-3
Uridine 3'-carbamate

D: 6195-72-8
1-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2-oxotetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-pyrimidine-2,4(1H,3H)-dione

Conditions

Conditions	Yield
With bromocyane; triethylamine In water at 2℃; for 45h; Further byproducts given;	A 13% B 37% C 27% D 4%

...Expand

: 58-96-8
uridine

A: 3736-77-4
2,2'-Anhydrouridine

B: 3083-77-0
araU

Conditions

Conditions	Yield
With bis(phenyl) carbonate; copper; sodium hydrogencarbonate In N,N,N,N,N,N-hexamethylphosphoric triamide at 150℃; for 20h;	A 30% B 35%

: 28321-79-1
diiminosuccinonitrile

: 3106-18-1
uridine-5'-monophosphate sodium

A: 3736-77-4
2,2'-Anhydrouridine

B: 3083-77-0
araU

C: 87186-13-8
2,2'-Anhydrouridine 3'-carbamate

D: 89998-90-3
Uridine 3'-carbamate

Conditions

Conditions	Yield
With Imidazole hydrochloride at 2℃; for 72h; Further byproducts given;	A 21% B 6% C 32% D 8%

...Expand

: 28321-79-1
diiminosuccinonitrile

: 3106-18-1
uridine-5'-monophosphate sodium

A: 3736-77-4
2,2'-Anhydrouridine

B: 3083-77-0
araU

C: 87186-13-8
2,2'-Anhydrouridine 3'-carbamate

D: 89998-90-3
Uridine 3'-carbamate

E: 89998-91-4
2'-O-carbamoyluridine

F: 6195-72-8
1-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2-oxotetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-pyrimidine-2,4(1H,3H)-dione

Conditions

Conditions	Yield
With bovine alkaline phosphatase or with BrCN;	A 21% B 6% C 32% D 8% E 2% F 3%

...Expand

: 1024-99-3
5-iodouridine

A: 3083-77-0
araU

B: 3052-06-0
1-β-D-arabinofuranosyl-5-iodouracil

Conditions

Conditions	Yield
With bis(phenyl) carbonate; copper; sodium hydrogencarbonate In N,N-dimethyl-formamide at 140 - 150℃;

: 112475-38-4
ara-UpUpU

: 3083-77-0
araU

Conditions

Conditions	Yield
With snake venom diasterease Product distribution;

: 292037-79-7
O2,2'-anhydro-1-(β-D-arabinofuranosyl)uracil

: 3083-77-0
araU

Conditions

Conditions	Yield
With sodium hydroxide In water Ambient temperature;

: 147-94-4
arabinosyl cytosine

A: 3083-77-0
araU

B: 66-22-8
uracil

Conditions

Conditions	Yield
With water at 90℃; Rate constant; pH 3.63;

: 52769-97-8
ara-UpU

: 3083-77-0
araU

Conditions

Conditions	Yield
With snake venom diasterease Product distribution;

: 1-(2',3',5'-tri-O-acetyl-β-D-arabinofuranosyl)-5-trimethylstannyl pyrimidine-2,4(3H)-dione

A: 1-(β-D-arabinofuranosyl)-5-[125I]iodopyrimidin-2,4(3H)-dione

B: 3083-77-0
araU

Conditions

Conditions	Yield
Stage #1: 1-(2',3',5'-tri-O-acetyl-β-D-arabinofuranosyl)-5-trimethylstannyl pyrimidine-2,4(3H)-dione With hexamethyldistannane; bis-triphenylphosphine-palladium(II) chloride In 1,4-dioxane at 100℃; for 2h; Stage #2: With sodium methylate In methanol at 0℃; for 7h; Stage #3: With sodium hydroxide; sodium (¹²⁵I)iodide; acetic acid; dihydrogen peroxide In chloroform for 0.0166667h; Further stages.;

Yield

Stage #1: 1-(2',3',5'-tri-O-acetyl-β-D-arabinofuranosyl)-5-trimethylstannyl pyrimidine-2,4(3H)-dione With hexamethyldistannane; bis-triphenylphosphine-palladium(II) chloride In 1,4-dioxane at 100℃; for 2h;
Stage #2: With sodium methylate In methanol at 0℃; for 7h;
Stage #3: With sodium hydroxide; sodium (¹²⁵I)iodide; acetic acid; dihydrogen peroxide In chloroform for 0.0166667h; Further stages.;

: 1-(2',3',5'-tri-O-acetyl-β-D-arabinofuranosyl)-5-trimethylstannyl pyrimidine-2,4(3H)-dione

: 3083-77-0
araU

Conditions

Conditions	Yield
With sodium methylate In methanol at 0℃; for 7h;

: 3868-21-1
2',3'-O-isopropylidene-O2,5'-cyclouridine

: 3083-77-0
araU

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: NaH, H2(17)O (54.75percent) / dimethylformamide 2: CF3COOH (90percent) 3: 79 percent / (C6H5O)2CO / dimethylformamide 4: 61 percent / LiOH View Scheme

: 362-43-6
2',3'-O-isopropylideneuridine

: 3083-77-0
araU

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: CF3COOH (90percent) 2: 79 percent / (C6H5O)2CO / dimethylformamide 3: 61 percent / LiOH View Scheme
Multi-step reaction with 5 steps 1: pyridine 2: aqueous acetic acid 3: pyridine 4: methanol. NH3 5: aqueous H2SO4 View Scheme

: 1748-04-5
tribenzoyl uridine

: 3083-77-0
araU

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 83 percent / Et3N / methanol; H2O 2: 79 percent / (C6H5O)2CO / dimethylformamide 3: 61 percent / LiOH View Scheme

: 4418-14-8
1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-4-chloro-2(1H)-pyrimidinone

: 3083-77-0
araU

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: H2(17)O (54.75percent) / CHCl3 2: 83 percent / Et3N / methanol; H2O 3: 79 percent / (C6H5O)2CO / dimethylformamide 4: 61 percent / LiOH View Scheme

: 10212-25-6
ancitabine hydrochloride

: 3083-77-0
araU

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 2 M KOH / H2O / 0.33 h / Ambient temperature; pH=10.3 2: cytidine deaminase ( EC 3.5.4.5 ) / 48 h / 37 °C / pH=6.8 with acetic acid View Scheme

: 3106-18-1
uridine-5'-monophosphate sodium

: 3083-77-0
araU

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / H2O / 1.33 h / 2 °C 2: 90 percent / H2O, triethylamine / 48 h / 60 °C View Scheme

: 3083-77-0
araU

: 108-24-7
acetic anhydride

: 14057-18-2
1-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)uracil

Conditions

Conditions	Yield
With dmap	100%
With dmap; triethylamine In acetonitrile at 20℃;	96%
With pyridine at 4℃; for 24h;	91%

: 3083-77-0
araU

: 146-77-0
2-Chloroadenosine

: 10147-12-3
2-chloro-9-(β-D-arabinofuranosyl)adenine

Conditions

Conditions	Yield
With uridine phosphorylase; disodium hydrogen arsenate heptahydrate; Escherichia coli purine nucleoside phosphorylase for 48h; Enzymatic reaction;	99%

: 3083-77-0
araU

: 58-63-9
inosine

: 7013-16-3
9-(β-D-arabinofuranosyl)-9H-purin-6(1H)-one

Conditions

Conditions	Yield
With uridine phosphorylase; disodium hydrogen arsenate heptahydrate; Escherichia coli purine nucleoside phosphorylase for 48h; Enzymatic reaction;	98%

: 3083-77-0
araU

: 18162-48-6
tert-butyldimethylsilyl chloride

: 82845-94-1
1-[(2R,3S,4R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

Conditions

Conditions	Yield
With silver nitrate; triethylamine In 1,2-dimethoxyethane for 5h; Ambient temperature;	96%
With triethylamine; silver nitrate In 1,2-dimethoxyethane for 5h;	96%

: 3083-77-0
araU

A: α-D-arabinofuranosyl-1-phosphate barium salt

B: 66-22-8
uracil

Conditions

Conditions	Yield
Stage #1: araU With magnesium(II) chloride hexahydrate; recombinant E. coli uridine phosphorylase In aq. phosphate buffer at 40℃; for 72h; pH=7.0; Stage #2: With ammonium hydroxide; barium(II) acetate In aq. phosphate buffer at 4℃; pH=8.0;	A 96% B n/a

: 613-90-1
benzoyl cyanide

: 3083-77-0
araU

: 4348-69-0
1-(tri-O-benzoyl-β-D-arabinofuranosyl)-1H-pyrimidine-2,4-dione

Conditions

Conditions	Yield
With triethylamine In acetonitrile for 2h; Ambient temperature;	95%

: 106-43-4
para-chlorotoluene

: 3083-77-0
araU

: 81777-54-0
1-(2,3,5-tri-O-p-toluyl-β-D-arabinofuranosyl)uracil

Conditions

Conditions	Yield
In pyridine 1.) 0 degC to R.T., 2.) 50 degC, 2 h;	95%

: 3083-77-0
araU

: 18162-48-6
tert-butyldimethylsilyl chloride

: 82845-98-5
1-<3,5-bis-O-(tert-butyldimethylsilyl)-β-D-arabinofuranosyl>-uracil

Conditions

Conditions	Yield
With 3-picoline-N-oxide; silver nitrate In tetrahydrofuran for 2h; Ambient temperature;	95%
With 3-picoline-N-oxide; silver nitrate In tetrahydrofuran for 1.5h;	95%

: 3083-77-0
araU

: 957-75-5, 3266-88-4, 3370-69-2, 38953-77-4, 82950-04-7
aBrUra

Conditions

Conditions	Yield
With N-Bromosuccinimide; sodium azide In 1,2-dimethoxyethane; water at 25℃; for 24h;	95%
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In N,N-dimethyl-formamide at 25℃; for 1h;	65%
With N-Bromosuccinimide In ethanol; chloroform; N,N-dimethyl-formamide

: 3083-77-0
araU

: 7803-88-5
6-O-methylguanosine

: 9-(β-D-Arabinofuranosyl)-2-amino-6-methoxy-9H-purine

Conditions

Conditions	Yield
With potassium dihydrogenphosphate; uridine phosphorylase; disodium hydrogen arsenate heptahydrate; Escherichia coli purine nucleoside phosphorylase In aq. phosphate buffer at 52 - 55℃; for 168h; pH=7; Enzymatic reaction;	95%

: 3083-77-0
araU

: 58-61-7
adenosine

: 5536-17-4
arabinosyl adenine

Conditions

Conditions	Yield
With uridine phosphorylase; disodium hydrogen arsenate heptahydrate; Escherichia coli purine nucleoside phosphorylase In aq. phosphate buffer at 52℃; for 16h; pH=7; Enzymatic reaction;	93%

: 3083-77-0
araU

: 66224-66-6, 66224-67-7, 66224-68-8, 66224-69-9, 134434-48-3, 134434-49-4, 134454-76-5, 134461-75-9
adenine

: 5536-17-4
arabinosyl adenine

Conditions

Conditions	Yield
With phosphate buffer; cell paste of Enterobacter aerogenes AJ 11125 at 60℃; for 15h; pH 7.0; several purine bases also investigated;	92%
With phosphate buffer; cell paste of Enterobacter aerogenes AJ 11125 at 60℃; for 15h; pH 7.0;	92%
With potassium dihydrogenphosphate at 60℃; for 15h; Enterobacter aerogenes AJ 11125, pH 7.0;	87%

: 3083-77-0
araU

: 146-78-1
2-fluoroadenosine

: 146-78-1, 19768-92-4, 21679-14-1, 21679-15-2
Fludarabine

Conditions

Conditions	Yield
With uridine phosphorylase; disodium hydrogen arsenate heptahydrate; Escherichia coli purine nucleoside phosphorylase In aq. phosphate buffer at 52℃; pH=7; Enzymatic reaction;	92%

: 40615-36-9
4,4'-dimethoxytrityl chloride

: 3083-77-0
araU

: 82854-27-1
1-{(2R,3S,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3,4-dihydroxy-tetrahydro-furan-2-yl}-1H-pyrimidine-2,4-dione

Conditions

Conditions	Yield
With pyridine at -5℃; for 1h;	90%

: 3083-77-0
araU

: 18162-48-6
tert-butyldimethylsilyl chloride

A: 82845-98-5
1-<3,5-bis-O-(tert-butyldimethylsilyl)-β-D-arabinofuranosyl>-uracil

B: 82845-94-1
1-[(2R,3S,4R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

C: 87418-77-7
1-[(2R,3S,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

Conditions

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide for 40h; Product distribution; further solvents, reaction times, reagents, reagents and catalyst concentration,;	A 6% B 2% C 90%
With 1H-imidazole In N,N-dimethyl-formamide for 40h;	A 6% B 2% C 90%

...Expand

: 3083-77-0
araU

: 14470-28-1
mono-4-methoxytrityl chloride

: 87418-73-3
5'-O-monomethoxytritylarabinouridine

Conditions

Conditions	Yield
With pyridine at 50℃;	90%

: 3083-77-0
araU

: 30100-83-5
1-(β-D-arabinofuranosyl)-5,6-dihydrouracil

Conditions

Conditions	Yield
With hydrogen; Rh on carbon In water under 2400.2 Torr; for 16h; Ambient temperature;	90%

: 3083-77-0
araU

: 3052-06-0
1-β-D-arabinofuranosyl-5-iodouracil

Conditions

Conditions	Yield
With sodium azide; Iodine monochloride In acetonitrile at 25℃; for 36h;	90%
With ammonium cerium (IV) nitrate; iodine; acetic acid at 80℃; for 1h;	82%
With iodine; nitric acid In chloroform	62%
Multi-step reaction with 3 steps 1: 89 percent / pyridine / 0.5 h / 20 °C 2: 70 percent / I2; ceric(IV) ammonium nitrate / acetonitrile / 1 h / 80 °C 3: 80 percent / NaOMe / methanol / 0.5 h / 20 °C View Scheme
With iodine; nitric acid In chloroform

: 3083-77-0
araU

: 106-96-7
propargyl bromide

: 1-(β-D-arabinofuranosyl)-3-(prop-2-yn-1-yl)uracil

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃;	90%

: 69304-37-6
1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane

: 3083-77-0
araU

: 104477-70-5
5',3'-O-(tetraisopropyldisiloxane-1,3-di-yl)-1-β-D-arabinofuranosyl-uracil

Conditions

Conditions	Yield
With pyridine at 0 - 20℃;	89%
With pyridine at 5 - 22℃; under 24 Torr; for 3h; regioselective reaction;	86%
With pyridine at 0 - 20℃;	60.3%
With pyridine
With pyridine

: 3083-77-0
araU

: 108-24-7
acetic anhydride

: 84500-33-4
1-(2',3',5'-tri-O-acetyl-β-D-arabinofuranosyl)-5-iodo-pyrimidine-2,4(3H)-dione

Conditions

Conditions	Yield
Stage #1: araU; acetic anhydride With pyridine Stage #2: With ammonium cerium(IV) nitrate; iodine In acetonitrile	88%

: 3083-77-0
araU

: 1904-98-9
2,6-diaminopurine

: 34079-68-0
2,6-diamino-9-(β-D-arabinofuranosyl)-purine

Conditions

Conditions	Yield
With phosphate buffer; cell paste of Enterobacter aerogenes AJ 11125 at 60℃; for 15h; pH 7.0;	83%
With dipotassium hydrogenphosphate; sodium azide; purine nucleoside phodphorylase ( EC 2.4.2.1 ); uridine phosphorylase ( EC 2.4.2.3 ) at 37℃; for 288h; pH=7.1; Yield given;
With potassium phosphate; Geobacillus thermoglucosidasius purine nucleoside phosphorylase; Thermus thermophilus pyrimidine nucleoside phosphorylase In water at 70℃; for 3h; pH=7; Enzymatic reaction;

: 3083-77-0
araU

: 133360-56-2
propan-2-one O-butyryl oxime

: 1-(5-O-butanoyl-β-D-arabinofuranosyl)uracil

Conditions

Conditions	Yield
In tetrahydrofuran at 60℃; for 7h; lipase from Candida antarctica (CAL SP435L);	81%

: 2466-76-4
N-Acetylimidazole

: 3083-77-0
araU

: 14057-18-2
1-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)uracil

Conditions

Conditions	Yield
With sodium hydroxide In water at 20℃; for 4h; pH=8;	78%

: 2051-49-2
n-hexanoic anhydride

: 3083-77-0
araU

A: 1-(5-O-hexanoyl-β-D-arabinofuranosyl)uracil

B: Hexanoic acid (2R,3S,4S,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-yl ester

Conditions

Conditions	Yield
In 1,4-dioxane for 3h; Ambient temperature; Lipase SP435;	A 77% B 3%

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Spongouridine Specification

The Arabinofuranosyluracil, with the CAS registry number 3083-77-0 and EINECS registry number 221-386-9, has the IUPAC name of 1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione. It is a kind of white to off-white solid, and belongs to the following product categories: Bases & Related Reagents; Carbohydrates & Derivatives; Intermediates & Fine Chemicals; Nucleotides; Pharmaceuticals. And the molecular formula of the chemical is C₉H₁₂N₂O₆. What's more, it is a kind of antiviral agent, and always used for the treatment of severe acute respiratory syndrome (SARS). Besides, it should be stored at 2-8 °C.

The physical properties of Arabinofuranosyluracil are as followings: (1)ACD/LogP: -1.61; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.61; (4)ACD/LogD (pH 7.4): -1.67; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 3.16; (8)ACD/KOC (pH 7.4): 2.79; (9)#H bond acceptors: 8; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 77.54 Å²; (13)Index of Refraction: 1.643; (14)Molar Refractivity: 52.73 cm³; (15)Molar Volume: 145.7 cm³; (16)Polarizability: 20.9×10^-24cm³; (17)Surface Tension: 88.5 dyne/cm; (18)Density: 1.674 g/cm³.

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 avoid contacting with skin and eyes; Wear suitable protective clothing, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C/1NC(=O)N(\C=C\1)C2OC(C(O)C2O)CO
(2)InChI: InChI=1/C9H12N2O6/c12-3-4-6(14)7(15)8(17-4)11-2-1-5(13)10-9(11)16/h1-2,4,6-8,12,14-15H,3H2,(H,10,13,16)
(3)InChIKey: DRTQHJPVMGBUCF-UHFFFAOYAQ

Product Name

Spongouridine

Synthetic route

Spongouridine Specification

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