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134790-39-9

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134790-39-9 Usage

Chemical Properties

Tan Solid

Uses

Different sources of media describe the Uses of 134790-39-9 differently. You can refer to the following data:
1. A (-anomer) intermediate of Gemcitabine; antitumor compound
2. A (β-anomer) intermediate of Gemcitabine; antitumor compound.

Check Digit Verification of cas no

The CAS Registry Mumber 134790-39-9 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,4,7,9 and 0 respectively; the second part has 2 digits, 3 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 134790-39:
(8*1)+(7*3)+(6*4)+(5*7)+(4*9)+(3*0)+(2*3)+(1*9)=139
139 % 10 = 9
So 134790-39-9 is a valid CAS Registry Number.

134790-39-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

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

1.2 Other means of identification

Product number -
Other names 3',5'-Di-O-benzoyl-2'-deoxy-2',2'-difluorocytidine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:134790-39-9 SDS

134790-39-9Synthetic route

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

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

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

(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate
134790-39-9

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

Conditions
ConditionsYield
In toluene at 120℃; for 6h; Temperature;97.38%
4-Amino-1-trimethylsilanyl-1H-pyrimidin-2-one
73416-12-3

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

2-deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-diphenylmethyl ester-1-methanesulfonate
134877-42-2

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

(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate
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%
2-deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-diphenylmethyl ester-1-methanesulfonate
134877-42-2

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

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

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

(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate
134790-39-9

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

Conditions
ConditionsYield
at 120℃; for 3h; Heating;85.5%
3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-D-erythro-pentofuranose
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

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

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

A

C23H19F2N3O6
134790-40-2

C23H19F2N3O6

B

(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate
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;
(2R,3R)-2-((benzoyloxy)methyl)-4,4-difluoro-5-hydroxyoxolan-3-yl benzoate
1173824-58-2

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

(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate
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
2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate
122111-01-7

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

(2'-deoxy-2',2'-difluorocytidine)-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
Cytosine
71-30-7

Cytosine

2-deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-diphenylmethyl ester-1-methanesulfonate
134877-42-2

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

A

C23H19F2N3O6
134790-40-2

C23H19F2N3O6

B

(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate
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
3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-D-erythro-pentofuranose
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

(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate
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
(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate
134790-39-9

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

C23H20F2N2O7

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;
(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate
134790-39-9

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

gemcitabine
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'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate
134790-39-9

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

Benzoic acid (2R,3R,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-4,4-difluoro-3-hydroxy-tetrahydro-furan-2-ylmethyl ester

Benzoic acid (2R,3R,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-4,4-difluoro-3-hydroxy-tetrahydro-furan-2-ylmethyl ester

Conditions
ConditionsYield
With ammonia In methanol
(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate
134790-39-9

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

C34H55F2N3O8

C34H55F2N3O8

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: dmap; triethylamine / 1,4-dioxane / 5 h / 40 °C
2: sodium hydroxide / methanol / 4 h / 20 °C
3: triethylamine / dichloromethane / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: N,N-lutidine / 1,4-dioxane / 5 h / 40 °C
2: sodium hydroxide; sodium methylate / 4 h / 20 °C
3: triethylamine / dichloromethane / 20 °C
View Scheme
(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate
134790-39-9

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

2',2'-difluoro-2'-deoxycytidine 3',5'-di-n-decanoate

2',2'-difluoro-2'-deoxycytidine 3',5'-di-n-decanoate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: dmap; triethylamine / 1,4-dioxane / 5 h / 40 °C
2: sodium hydroxide / methanol / 4 h / 20 °C
3: triethylamine / dichloromethane / 20 °C
4: trifluoroacetic acid / dichloromethane / 4 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: N,N-lutidine / 1,4-dioxane / 5 h / 40 °C
2: sodium hydroxide; sodium methylate / 4 h / 20 °C
3: triethylamine / dichloromethane / 20 °C
4: trifluoroacetic acid / dichloromethane / 4 h / 20 °C
View Scheme
(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate
134790-39-9

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

C30H37F2N3O6Si

C30H37F2N3O6Si

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: dmap; triethylamine / 1,4-dioxane / 5 h / 40 °C
2: sodium hydroxide / methanol / 4 h / 20 °C
3: dmap / N,N-dimethyl-formamide / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: N,N-lutidine / 1,4-dioxane / 5 h / 40 °C
2: sodium hydroxide; sodium methylate / 4 h / 20 °C
3: N,N-lutidine / N,N-dimethyl-formamide / 20 °C
View Scheme
(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate
134790-39-9

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

tert-butyl [1-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-hydroxymethyl-tetrahydrofuran-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-carbamate

tert-butyl [1-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-hydroxymethyl-tetrahydrofuran-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-carbamate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dmap; triethylamine / 1,4-dioxane / 5 h / 40 °C
2: sodium hydroxide / methanol / 4 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: N,N-lutidine / 1,4-dioxane / 5 h / 40 °C
2: sodium hydroxide; sodium methylate / 4 h / 20 °C
View Scheme
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate
134790-39-9

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

C28H27F2N3O8

C28H27F2N3O8

Conditions
ConditionsYield
With dmap; triethylamine In 1,4-dioxane at 40℃; for 5h;
With N,N-lutidine In 1,4-dioxane at 40℃; for 5h;
3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-D-erythro-pentofuranose
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

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

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

(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate
134790-39-9

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

Conditions
ConditionsYield
In toluene at 120℃; for 6h; Temperature;97.38%
4-Amino-1-trimethylsilanyl-1H-pyrimidin-2-one
73416-12-3

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

2-deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-diphenylmethyl ester-1-methanesulfonate
134877-42-2

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

(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate
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%
2-deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-diphenylmethyl ester-1-methanesulfonate
134877-42-2

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

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

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

(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate
134790-39-9

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

Conditions
ConditionsYield
at 120℃; for 3h; Heating;85.5%
3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-D-erythro-pentofuranose
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

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

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

A

C23H19F2N3O6
134790-40-2

C23H19F2N3O6

B

(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate
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;
(2R,3R)-2-((benzoyloxy)methyl)-4,4-difluoro-5-hydroxyoxolan-3-yl benzoate
1173824-58-2

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

(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate
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
2-deoxy-2,2-difluoro-D-erythro-pentonic acid γ-lactone 3,5-dibenzoate
122111-01-7

2-deoxy-2,2-difluoro-D-erythro-pentonic acid γ-lactone 3,5-dibenzoate

(2'-deoxy-2',2'-difluorocytidine)-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
Cytosine
71-30-7

Cytosine

2-deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-diphenylmethyl ester-1-methanesulfonate
134877-42-2

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

A

C23H19F2N3O6
134790-40-2

C23H19F2N3O6

B

(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate
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
3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-D-erythro-pentofuranose
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

(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate
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
(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate
134790-39-9

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

C23H20F2N2O7

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;
(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate
134790-39-9

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

gemcitabine
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'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate
134790-39-9

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

Benzoic acid (2R,3R,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-4,4-difluoro-3-hydroxy-tetrahydro-furan-2-ylmethyl ester

Benzoic acid (2R,3R,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-4,4-difluoro-3-hydroxy-tetrahydro-furan-2-ylmethyl ester

Conditions
ConditionsYield
With ammonia In methanol
(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate
134790-39-9

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

C23H22F2N2O7

C23H22F2N2O7

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: hydrogenchloride / ethyl acetate; water / 0.08 h
1.2: 24 h / 68 - 70 °C / Inert atmosphere
2.1: cerium(III) chloride heptahydrate / dichloromethane; ethanol / 0.08 h
2.2: 2 h / 0 - 6 °C
View Scheme
Multi-step reaction with 2 steps
1: acetic acid; palladium 10% on activated carbon; hydrogen / ethyl acetate; water / 18 h / 50 - 60 °C / 3750.38 Torr
2: cerium(III) chloride heptahydrate; sodium tetrahydroborate / water; dichloromethane; ethanol / 2 h / 6 °C
View Scheme
(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate
134790-39-9

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

2’-deoxy-2’,2’-difluorotetrahydrouridine
1141397-48-9

2’-deoxy-2’,2’-difluorotetrahydrouridine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: hydrogenchloride / ethyl acetate; water / 0.08 h
1.2: 24 h / 68 - 70 °C / Inert atmosphere
2.1: cerium(III) chloride heptahydrate / dichloromethane; ethanol / 0.08 h
2.2: 2 h / 0 - 6 °C
3.1: ammonia / methanol / 27 h / 25 °C
View Scheme
Multi-step reaction with 3 steps
1: acetic acid; palladium 10% on activated carbon; hydrogen / ethyl acetate; water / 18 h / 50 - 60 °C / 3750.38 Torr
2: cerium(III) chloride heptahydrate; sodium tetrahydroborate / water; dichloromethane; ethanol / 2 h / 6 °C
3: 1,8-diazabicyclo[5.4.0]undec-7-ene / methanol / 3 h / 40 °C
View Scheme
(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate
134790-39-9

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

(4R)-2’-deoxy-2’,2’-difluoro-3,4,5,6-tetrahydrouridine
1141397-80-9

(4R)-2’-deoxy-2’,2’-difluoro-3,4,5,6-tetrahydrouridine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: hydrogenchloride / ethyl acetate; water / 0.08 h
1.2: 24 h / 68 - 70 °C / Inert atmosphere
2.1: cerium(III) chloride heptahydrate / dichloromethane; ethanol / 0.08 h
2.2: 2 h / 0 - 6 °C
3.1: ammonia / methanol / 27 h / 25 °C
4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / water; acetonitrile / 74 h / 25 °C / Large scale
4.2: 16 h / 0 - 40 °C / Large scale
View Scheme
Multi-step reaction with 4 steps
1: acetic acid; palladium 10% on activated carbon; hydrogen / ethyl acetate; water / 18 h / 50 - 60 °C / 3750.38 Torr
2: cerium(III) chloride heptahydrate; sodium tetrahydroborate / water; dichloromethane; ethanol / 2 h / 6 °C
3: 1,8-diazabicyclo[5.4.0]undec-7-ene / methanol / 3 h / 40 °C
4: 1,8-diazabicyclo[5.4.0]undec-7-ene / water; acetonitrile / 48 h / 20 - 30 °C
View Scheme
(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate
134790-39-9

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

C9H9F2N3O6P(1-)*Na(1+)

C9H9F2N3O6P(1-)*Na(1+)

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: ammonium hydroxide / methanol / 3 h / 20 °C
2.1: pyridine; trichlorophosphate / 0 - 20 °C
2.2: 0.5 h / pH 3 - 4
3.1: sodium hydrogencarbonate / ethanol; water / 3 h
View Scheme
(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate
134790-39-9

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

1-[(4aR,6R,7aR)-7,7-difluoro-2-hydroxy-2-oxo-4,4a,6,7a-tetrahydrofuro[3,2-d][1,3,2]dioxaphosphinin-6-yl]-4-amino-pyrimidin-2-one

1-[(4aR,6R,7aR)-7,7-difluoro-2-hydroxy-2-oxo-4,4a,6,7a-tetrahydrofuro[3,2-d][1,3,2]dioxaphosphinin-6-yl]-4-amino-pyrimidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: ammonium hydroxide / methanol / 3 h / 20 °C
2.1: pyridine; trichlorophosphate / 0 - 20 °C
2.2: 0.5 h / pH 3 - 4
View Scheme
(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate
134790-39-9

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

C34H55F2N3O8

C34H55F2N3O8

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: dmap; triethylamine / 1,4-dioxane / 5 h / 40 °C
2: sodium hydroxide / methanol / 4 h / 20 °C
3: triethylamine / dichloromethane / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: N,N-lutidine / 1,4-dioxane / 5 h / 40 °C
2: sodium hydroxide; sodium methylate / 4 h / 20 °C
3: triethylamine / dichloromethane / 20 °C
View Scheme
(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate
134790-39-9

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

2',2'-difluoro-2'-deoxycytidine 3',5'-di-n-decanoate

2',2'-difluoro-2'-deoxycytidine 3',5'-di-n-decanoate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: dmap; triethylamine / 1,4-dioxane / 5 h / 40 °C
2: sodium hydroxide / methanol / 4 h / 20 °C
3: triethylamine / dichloromethane / 20 °C
4: trifluoroacetic acid / dichloromethane / 4 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: N,N-lutidine / 1,4-dioxane / 5 h / 40 °C
2: sodium hydroxide; sodium methylate / 4 h / 20 °C
3: triethylamine / dichloromethane / 20 °C
4: trifluoroacetic acid / dichloromethane / 4 h / 20 °C
View Scheme
(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate
134790-39-9

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

C30H37F2N3O6Si

C30H37F2N3O6Si

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: dmap; triethylamine / 1,4-dioxane / 5 h / 40 °C
2: sodium hydroxide / methanol / 4 h / 20 °C
3: dmap / N,N-dimethyl-formamide / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: N,N-lutidine / 1,4-dioxane / 5 h / 40 °C
2: sodium hydroxide; sodium methylate / 4 h / 20 °C
3: N,N-lutidine / N,N-dimethyl-formamide / 20 °C
View Scheme
(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate
134790-39-9

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

tert-butyl [1-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-hydroxymethyl-tetrahydrofuran-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-carbamate

tert-butyl [1-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-hydroxymethyl-tetrahydrofuran-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-carbamate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dmap; triethylamine / 1,4-dioxane / 5 h / 40 °C
2: sodium hydroxide / methanol / 4 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: N,N-lutidine / 1,4-dioxane / 5 h / 40 °C
2: sodium hydroxide; sodium methylate / 4 h / 20 °C
View Scheme
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate
134790-39-9

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

C28H27F2N3O8

C28H27F2N3O8

Conditions
ConditionsYield
With dmap; triethylamine In 1,4-dioxane at 40℃; for 5h;
With N,N-lutidine In 1,4-dioxane at 40℃; for 5h;
n-decyl chloroformate
55488-51-2

n-decyl chloroformate

(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate
134790-39-9

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

C34H39F2N3O8

C34H39F2N3O8

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 1.5h;
Reaxys ID: 37235391

Reaxys ID: 37235391

(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate
134790-39-9

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

Reaxys ID: 37235389

Reaxys ID: 37235389

134790-39-9Downstream Products

134790-39-9Relevant articles and documents

Preparation method of beta-configuration gemcitabine hydrochloride intermediate

-

Paragraph 0028; 0036-0054, (2021/04/01)

The invention provides a preparation method of a beta-configuration gemcitabine hydrochloride intermediate, which comprises the following step: in a solvent, in the presence of an alpha-configurationgemcitabine hydrochloride intermediate II', reacting a gemcitabine hydrochloride intermediate I with silanized cytosine to prepare the beta-configuration gemcitabine hydrochloride intermediate II. Thebeta-configuration gemcitabine hydrochloride intermediate II is prepared in the presence of the alpha-configuration gemcitabine hydrochloride intermediate II', and the production of the alpha-configuration gemcitabine hydrochloride intermediate is effectively inhibited, so that the yield and the purity of a target product, namely the beta-configuration gemcitabine hydrochloride intermediate II, are improved, and post-treatment steps are simplified.

A miazines new compounds

-

Paragraph 0007; 0010; 0011, (2017/07/07)

The invention relates to a new pyrimidine compound. The experiment proves that the new compound disclosed in the specification can inhibit growth of tumor cells, and has favorable effectiveness and safety when being used for preparing antineoplastic drugs. The vessel irritation experiment proves that the new compound does not have hemolysis or irritation and can be prepared into an injection for clinical use.

Stereospecific synthesis of 2-deoxy-2,2-difluororibonolactone and its use in the preparation of 2'-deoxy-2',2'-difluoro-β-D-ribofuranosyl pyrimidine nucleosides: The key role of selective crystallization

Chou,Heath,Patterson,Poteet,Lakin,Hunt

, p. 565 - 570 (2007/10/02)

A stereospecific synthesis of 2'-deoxy-2',2'-difluorocytidine (gemcitabine), a potential anticancer agent, is described. The stereoselectivity was accomplished via two diastereoselective crystallizations, i.e. the crystallization of the key intermediate, difluororibonolactone 2a, and the crystallization of the hydrochloride salt of gemcitabine 16b from the anomeric mixture. Because of the availability of 2a in large quantities, other 2'-deoxy-2',2'-difluoropyrimidine nucleosides such as 2'-deoxy-2',2'-difluorouridine (19) were synthesized for structure-activity relationship studies.

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