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Spongouridine

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Name

Spongouridine

EINECS 221-386-9
CAS No. 3083-77-0 Density 1.674 g/cm3
PSA 124.78000 LogP -2.85190
Solubility N/A Melting Point 220-222 °C
Formula C9H12N2O6 Boiling Point N/A
Molecular Weight 244.204 Flash Point N/A
Transport Information N/A Appearance white to off-white solid
Safety 22-24/25-36-26 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 3083-77-0 (Spongouridine) Hazard Symbols IrritantXi
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;

Article Data 64

Spongouridine Synthetic route

14057-18-2

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

Conditions
ConditionsYield
With keratinase from Paecilomyces marquandii for 216h; pH=8; aq. phosphate buffer; Enzymatic reaction;100%
147-94-4

arabinosyl cytosine

Conditions
ConditionsYield
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

Conditions
ConditionsYield
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

Conditions
ConditionsYield
With water; triethylamine at 60℃; for 48h;90%
28309-53-7

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

Conditions
ConditionsYield
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

Conditions
ConditionsYield
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

Conditions
ConditionsYield
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

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

C15H24N2O6

Conditions
ConditionsYield
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

C

87186-13-8

2,2'-Anhydrouridine 3'-carbamate

D

89998-90-3

Uridine 3'-carbamate

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

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

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