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2',2'-Difluoro-2'-deoxycytidine-3',5'-dibenzoate
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Name

2',2'-Difluoro-2'-deoxycytidine-3',5'-dibenzoate

 EINECS 603-873-1
CAS No. 134790-39-9 Density 1.459 g/cm3
PSA 122.74000 LogP 3.02200
Solubility N/A Melting Point 229-232°C
Formula C23H19F2N3O6 Boiling Point 608.383 °C at 760 mmHg
Molecular Weight 471.417 Flash Point 321.739 °C
Transport Information N/A Appearance Tan solid
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 134790-39-9 (2',2'-Difluoro-2'-deoxycytidine-3',5'-dibenzoate) Hazard Symbols N/A
Synonyms

3',5'-Di-O-benzoyl-2'-deoxy-2',2'-difluorocytidine; 2'-deoxy-2,2'-difluoro-3,5-dibenzyl-cytidine; Chloropurine riboside; GeMcitabine InterMediate 9;

Article Data 5

2',2'-Difluoro-2'-deoxycytidine-3',5'-dibenzoate Synthetic route

134877-42-2, 134877-43-3, 122111-11-9

3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-D-erythro-pentofuranose

18037-10-0

2,4-O,N-bis(trimethylsilyl)cytosine

134790-39-9

(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate

Conditions
ConditionsYield
In toluene at 120℃; for 6h; Temperature;97.38%
73416-12-3

4-Amino-1-trimethylsilanyl-1H-pyrimidin-2-one

134877-42-2

2-deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-diphenylmethyl ester-1-methanesulfonate

134790-39-9

(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate

Conditions
ConditionsYield
With phosphomolybdic acid In pentan-1-ol at 70 - 137℃; for 5h; Reagent/catalyst; Solvent; Temperature; Reflux;95%
134877-42-2

2-deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-diphenylmethyl ester-1-methanesulfonate

18037-10-0

2,4-O,N-bis(trimethylsilyl)cytosine

134790-39-9

(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate

Conditions
ConditionsYield
at 120℃; for 3h; Heating;85.5%
134877-42-2, 134877-43-3, 122111-11-9

3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-D-erythro-pentofuranose

18037-10-0

2,4-O,N-bis(trimethylsilyl)cytosine

A

134790-40-2

C23H19F2N3O6

B

134790-39-9

(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate 1) 1,1,2-trichloroethane, r.t., 30 min, 2) 113 deg C, 18 h; Yield given. Multistep reaction. Yields of byproduct given;
1173824-58-2

(2R,3R)-2-((benzoyloxy)methyl)-4,4-difluoro-5-hydroxyoxolan-3-yl benzoate

134790-39-9

(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 100 percent / triethylamine / CH2Cl2 / 2 h / 23 °C
2: 1) Me3SiOTf / 1) 1,1,2-trichloroethane, r.t., 30 min, 2) 113 deg C, 18 h
View Scheme
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 2 h / 5 - 20 °C
2: 3 h / 120 °C / Heating
View Scheme
122111-01-7

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate

134790-39-9

(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 100 percent / LiAl(OBu-t)3H / diethyl ether; tetrahydrofuran / 1 h / 10 - 30 °C
2: 100 percent / triethylamine / CH2Cl2 / 2 h / 23 °C
3: 1) Me3SiOTf / 1) 1,1,2-trichloroethane, r.t., 30 min, 2) 113 deg C, 18 h
View Scheme
71-30-7

Cytosine

134877-42-2

2-deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-diphenylmethyl ester-1-methanesulfonate

A

134790-40-2

C23H19F2N3O6

B

134790-39-9

(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate

Conditions
ConditionsYield
With potassium sulfate; lithium chloride at 120 - 125℃; for 4h; Overall yield = 85.7 %; Overall yield = 405.2 g;A n/a
B n/a
134877-42-2, 134877-43-3, 122111-11-9

3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-D-erythro-pentofuranose

134790-39-9

(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ethanol / 50 - 60 °C
2: 3 h / 120 °C / Heating
View Scheme
134790-39-9

(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate

C23H20F2N2O7

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen; acetic acid In water; ethyl acetate at 50 - 60℃; under 3750.38 Torr; for 18h;95.6%
Stage #1: (2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate With hydrogenchloride In water; ethyl acetate for 0.0833333h;
Stage #2: With formic acid; 5%-palladium/activated carbon In water; ethyl acetate at 68 - 70℃; for 24h; Inert atmosphere;
134790-39-9

(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate

95058-81-4

gemcitabine

Conditions
ConditionsYield
With ammonium hydroxide In methanol at 20℃; for 3h;82.7%
With sodium t-butanolate In methanol at 20℃; for 2h;

2',2'-Difluoro-2'-deoxycytidine-3',5'-dibenzoate Chemical Properties

Following is the structure of 2',2'-Difluoro-2'-deoxycytidine-3',5'-dibenzoate (CAS NO.134790-39-9):
                     
Empirical Formula: C23H19F2N3O6
Molecular Weight: 471.4103 g/mol
Molar Refractivity: 114.273 cm3
Molar Volume: 323.151 cm3
Density: 1.459 g/cm3
Flash Point: 321.739 °C
Index of Refraction: 1.625
Surface Tension: 53.506 dyne/cm
Enthalpy of Vaporization: 90.392 kJ/mol
Boiling Point of 2',2'-Difluoro-2'-deoxycytidine-3',5'-dibenzoate (CAS NO.134790-39-9): 608.383 °C at 760 mmHg
Appearance of 2',2'-Difluoro-2'-deoxycytidine-3',5'-dibenzoate (CAS NO.134790-39-9): Tan Solid
SMILES: O=C1/N=C(/N)\C=C/N1[C@@H]3O[C@@H]([C@@H](OC(=O)c2ccccc2)C3(F)F)COC(=O)c4ccccc4
InChI: InChI=1/C23H19F2N3O6/c24-23(25)18(34-20(30)15-9-5-2-6-10-15)16(13-32-19(29)14-7-3-1-4-8-14)33-21(23)28-12-11-17(26)27-22(28)31/h1-12,16,18,21H,13H2,(H2,26,27,31)/t16-,18-,21-/m1/s1
InChIKey: ZPUUYUUQQGBHBU-HGHGUNKEBC

2',2'-Difluoro-2'-deoxycytidine-3',5'-dibenzoate Uses

 2',2'-Difluoro-2'-deoxycytidine-3',5'-dibenzoate (CAS NO.134790-39-9) can be used as a (-anomer) intermediate of Gemcitabine ; antitumor compound.

2',2'-Difluoro-2'-deoxycytidine-3',5'-dibenzoate Specification

 2',2'-Difluoro-2'-deoxycytidine-3',5'-dibenzoate , its cas register number is 134790-39-9. It also can be called 3',5'-Di-O-benzoyl-2'-deoxy-2',2'-difluorocytidine ; and Cytidine, 2'-deoxy-2',2'-difluoro-, 3',5'-dibenzoate .

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