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764659-72-5

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  • (1R,2S,5R)-5-Methyl-2-(1-methylethyl)-cyclohexyl (2R,5S)-5-[4-amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl]-1,3-oxathiolane-2-carboxylate

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  • TIANFU-CHEM (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-Oxathiolane-2-carboxylic acid, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester

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  • 1,3-Oxathiolane-2-carboxylic acid, 5-(4-amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester, (2R,5S)- 764659-72-5

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  • (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-Oxathiolane-2-carboxylic acid, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester

    Cas No: 764659-72-5

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764659-72-5 Usage

Chemical Properties

(2R,5S)-5-(4-amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-Oxathiolane-2-carboxylic acid, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester is Off-White Solid

Uses

(2R,5S)-5-(4-amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-Oxathiolane-2-carboxylic acid, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester is an intermediate in the synthesis of Emtricitabine (E525000). A reverse transcriptase inhibitor. It is an effective antiviral agent against HIV, HBV, and other viruses replicating in a similar manner. A nucleoside analog structurally related to Lamivudine (L172500).

Check Digit Verification of cas no

The CAS Registry Mumber 764659-72-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 7,6,4,6,5 and 9 respectively; the second part has 2 digits, 7 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 764659-72:
(8*7)+(7*6)+(6*4)+(5*6)+(4*5)+(3*9)+(2*7)+(1*2)=215
215 % 10 = 5
So 764659-72-5 is a valid CAS Registry Number.

764659-72-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name [(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] 5-(4-amino-5-fluoro-2-oxopyrimidin-1-yl)-1,3-oxathiolane-2-carboxylate

1.2 Other means of identification

Product number -
Other names -

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:764659-72-5 SDS

764659-72-5Synthetic route

C21H31FN4O4S

C21H31FN4O4S

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate
764659-72-5

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate

Conditions
ConditionsYield
With hydrogenchloride In dichloromethane; water at 20 - 25℃;96.7%
Flucytosine
2022-85-7

Flucytosine

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5R)-5-(methylcarbonyloxy)-1,3-oxathiolane-2-carboxylate
147027-09-6

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5R)-5-(methylcarbonyloxy)-1,3-oxathiolane-2-carboxylate

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate
764659-72-5

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate

Conditions
ConditionsYield
Stage #1: (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5R)-5-(methylcarbonyloxy)-1,3-oxathiolane-2-carboxylate With triethylsilane; iodine In dichloromethane at 0℃; for 1h; Inert atmosphere;
Stage #2: Flucytosine With N,O-bis-(trimethylsilyl)-acetamide In dichloromethane at 0 - 20℃; for 1h; Reagent/catalyst; Inert atmosphere; stereoselective reaction;
91%
Stage #1: Flucytosine With chloro-trimethyl-silane; 1,1,1,3,3,3-hexamethyl-disilazane at 25 - 130℃; Inert atmosphere;
Stage #2: (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5R)-5-(methylcarbonyloxy)-1,3-oxathiolane-2-carboxylate With zirconium(IV) chloride In dichloromethane at 25 - 30℃; for 6h; Inert atmosphere;
80%
2-trimethylsilyloxy-4-trimethylsilylamino-5-fluoropyrimidine
111878-21-8

2-trimethylsilyloxy-4-trimethylsilylamino-5-fluoropyrimidine

5S-chloro-[1,3]oxathiolane-2R-carboxilic acid 2-(1'R,2'S,5'R)-isopropyl-5-methyl-cyclohexyl ester
288325-76-8

5S-chloro-[1,3]oxathiolane-2R-carboxilic acid 2-(1'R,2'S,5'R)-isopropyl-5-methyl-cyclohexyl ester

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate
764659-72-5

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate

Conditions
ConditionsYield
Stage #1: 2-trimethylsilyloxy-4-trimethylsilylamino-5-fluoropyrimidine; 5S-chloro-[1,3]oxathiolane-2R-carboxilic acid 2-(1'R,2'S,5'R)-isopropyl-5-methyl-cyclohexyl ester With triethylamine In dichloromethane at 42 - 45℃; for 19h; Heating / reflux;
Stage #2: With water at 25℃; for 0.5h;
81%
Flucytosine
2022-85-7

Flucytosine

5R-hydroxy-[1,3]oxathiolane-2R-carboxylic acid 2-(1'R,2'S,5'R)-isopropyl-5-methyl-cyclohexyl ester

5R-hydroxy-[1,3]oxathiolane-2R-carboxylic acid 2-(1'R,2'S,5'R)-isopropyl-5-methyl-cyclohexyl ester

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate
764659-72-5

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate

Conditions
ConditionsYield
Stage #1: 5R-hydroxy-[1,3]oxathiolane-2R-carboxylic acid 2-(1'R,2'S,5'R)-isopropyl-5-methyl-cyclohexyl ester With thionyl chloride In dichloromethane at 0 - 15℃; for 2h;
Stage #2: Flucytosine With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane In toluene Reflux;
Stage #3: With triethylamine at 90℃; Reflux;
50.5%
Stage #1: 5R-hydroxy-[1,3]oxathiolane-2R-carboxylic acid 2-(1'R,2'S,5'R)-isopropyl-5-methyl-cyclohexyl ester With thionyl chloride In dichloromethane; toluene; N,N-dimethyl-d6-formamide at 10 - 15℃; for 2h;
Stage #2: Flucytosine With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane In dichloromethane; N,N-dimethyl-formamide; toluene Reflux; Further stages;
50.5%
5-chloro-[1,3]oxathiolane-2-carboxylic acid 2-isopropyl-5-methyl-cyclohexyl ester

5-chloro-[1,3]oxathiolane-2-carboxylic acid 2-isopropyl-5-methyl-cyclohexyl ester

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate
764659-72-5

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate

Conditions
ConditionsYield
Stage #1: Flucytosine With methanesulfonic acid; 1,1,1,3,3,3-hexamethyl-disilazane In toluene for 3h;
Stage #2: 5-chloro-[1,3]oxathiolane-2-carboxylic acid 2-isopropyl-5-methyl-cyclohexyl ester With triethylamine In dichloromethane at 20 - 25℃; for 20 - 21h; Heating / reflux;
Multi-step reaction with 4 steps
1.1: triethylamine / dichloromethane / 8 - 50 °C
2.1: toluene / 1 h / Molecular sieve
3.1: toluene / 75 - 80 °C
4.1: methanesulfonic acid / methanol / 4 h
4.2: 0.17 h
View Scheme
(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(methylcarbonyloxy)-1,3-oxathiolane-2-carboxylate
147126-65-6

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(methylcarbonyloxy)-1,3-oxathiolane-2-carboxylate

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate
764659-72-5

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate

Conditions
ConditionsYield
Stage #1: Flucytosine With methanesulfonic acid; 1,1,1,3,3,3-hexamethyl-disilazane In toluene for 3h; Heating / reflux;
Stage #2: (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(methylcarbonyloxy)-1,3-oxathiolane-2-carboxylate With trimethylsilyl iodide In dichloromethane at 20℃; for 2h;
Flucytosine
2022-85-7

Flucytosine

(2R,5R)-5-hydroxy-[1,3]-oxathiolane-2-carboxylic acid, 2S-isopropyl-5R-methyl-1R-cyclohexyl ester

(2R,5R)-5-hydroxy-[1,3]-oxathiolane-2-carboxylic acid, 2S-isopropyl-5R-methyl-1R-cyclohexyl ester

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate
764659-72-5

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate

Conditions
ConditionsYield
Stage #1: (2R,5R)-5-hydroxy-[1,3]-oxathiolane-2-carboxylic acid, 2S-isopropyl-5R-methyl-1R-cyclohexyl ester With thionyl chloride; methanesulfonic acid; N,N-dimethyl-formamide In dichloromethane at 8 - 20℃; for 8h; Heating / reflux;
Stage #2: Flucytosine With 1,1,1,3,3,3-hexamethyl-disilazane In dichloromethane; toluene for 5h; Heating / reflux;
Stage #3: With triethylamine In dichloromethane; water; toluene at 25 - 65℃; for 6h; pH=7.8; Heating / reflux;
(2R,5R)-5-hydroxy-1,3-oxathiolane-2-carboxylic acid (1R,2S,5R)-5-methyl-2-isopropylcyclohexyl ester
147126-62-3

(2R,5R)-5-hydroxy-1,3-oxathiolane-2-carboxylic acid (1R,2S,5R)-5-methyl-2-isopropylcyclohexyl ester

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate
764659-72-5

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: pyridine / dmap / di-isopropyl ether / 5 - 20 °C
2.1: 1,1,1,3,3,3-hexamethyl-disilazane / methanesulfonic acid / toluene / 6 h / Reflux
2.2: 10 - 55 °C
3.1: methanesulfonic acid / di-isopropyl ether; methanol / 0.83 h / 20 °C
3.2: 1 h / 20 °C
View Scheme
(1'R,2'S,5'R)-menthyl-5(R,S)-acetoxy-[1,3]-oxathiolane-2R-carboxylate
1144099-18-2

(1'R,2'S,5'R)-menthyl-5(R,S)-acetoxy-[1,3]-oxathiolane-2R-carboxylate

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate
764659-72-5

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 1,1,1,3,3,3-hexamethyl-disilazane / methanesulfonic acid / toluene / 6 h / Reflux
1.2: 10 - 55 °C
2.1: methanesulfonic acid / di-isopropyl ether; methanol / 0.83 h / 20 °C
2.2: 1 h / 20 °C
View Scheme
C21H30FN3O5S

C21H30FN3O5S

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate
764659-72-5

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate

Conditions
ConditionsYield
Stage #1: C21H30FN3O5S With methanesulfonic acid In methanol; di-isopropyl ether at 20℃; for 0.833333h;
Stage #2: With triethylamine In hexane; water; ethyl acetate at 20℃; for 1h;
C21H32NO4S(1+)*I(1-)

C21H32NO4S(1+)*I(1-)

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate
764659-72-5

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: toluene / 75 - 80 °C
2.1: methanesulfonic acid / methanol / 4 h
2.2: 0.17 h
View Scheme
5-(4-acetylamino-5-fluoro-2-oxo-2H-pyrimidin-1-yl)-[1,3]oxathiolane-2-carboxylic acid 2-isopropyl-5-methyl-cyclohexyl ester
1321928-75-9

5-(4-acetylamino-5-fluoro-2-oxo-2H-pyrimidin-1-yl)-[1,3]oxathiolane-2-carboxylic acid 2-isopropyl-5-methyl-cyclohexyl ester

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate
764659-72-5

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate

Conditions
ConditionsYield
Stage #1: 5-(4-acetylamino-5-fluoro-2-oxo-2H-pyrimidin-1-yl)-[1,3]oxathiolane-2-carboxylic acid 2-isopropyl-5-methyl-cyclohexyl ester With methanesulfonic acid In methanol for 4h;
Stage #2: With sodium hydrogencarbonate In methanol; dichloromethane; water for 0.166667h; Product distribution / selectivity;
5-(pyridin-2-yloxy)-[1,3]oxathiolane-2-carboxylic acid 2-isopropyl-5-methyl-cyclohexyl ester
1321928-66-8

5-(pyridin-2-yloxy)-[1,3]oxathiolane-2-carboxylic acid 2-isopropyl-5-methyl-cyclohexyl ester

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate
764659-72-5

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: toluene / 1 h / Molecular sieve
2.1: toluene / 75 - 80 °C
3.1: methanesulfonic acid / methanol / 4 h
3.2: 0.17 h
View Scheme
5-hydroxy-[1,3]oxathiolane-2-carboxylic acid 2-isopropyl-5-methylcyclohexyl ester
1309459-32-2

5-hydroxy-[1,3]oxathiolane-2-carboxylic acid 2-isopropyl-5-methylcyclohexyl ester

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate
764659-72-5

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: N,N-dimethyl-formamide; methanesulfonic acid / dichloromethane / 8 - 12 °C
1.2: 2 h / 8 - 12 °C
2.1: triethylamine / dichloromethane / 8 - 50 °C
3.1: toluene / 1 h / Molecular sieve
4.1: toluene / 75 - 80 °C
5.1: methanesulfonic acid / methanol / 4 h
5.2: 0.17 h
View Scheme
L-menthol glyoxylate monohydrate
111969-64-3

L-menthol glyoxylate monohydrate

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate
764659-72-5

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: acetic acid / toluene / 50 - 115 °C
2.1: pyridine / dichloromethane / 0 - 5 °C / Inert atmosphere
3.1: 1,1,1,3,3,3-hexamethyl-disilazane; chloro-trimethyl-silane / 25 - 130 °C / Inert atmosphere
3.2: 6 h / 25 - 30 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: acetic acid / toluene / 2 h / 120 °C / Dean-Stark
1.2: 4 h / Reflux
1.3: 16 h / 0 °C
2.1: pyridine / dichloromethane / 0 - 20 °C / Inert atmosphere
3.1: triethylsilane; iodine / dichloromethane / 1 h / 0 °C / Inert atmosphere
3.2: 1 h / 0 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: acetic acid / toluene / 2 h / 120 °C / Dean-Stark
1.2: 4 h / Reflux
1.3: 16 h / 0 °C
2.1: acetic anhydride; pyridine / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere
2.2: 72 h / -20 °C
3.1: triethylsilane; iodine / dichloromethane / 1 h / 0 °C / Inert atmosphere
3.2: 1 h / 0 - 20 °C / Inert atmosphere
View Scheme
(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-hydroxy-1,3-oxathiolane-2-carboxylate
200396-19-6

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-hydroxy-1,3-oxathiolane-2-carboxylate

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate
764659-72-5

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: pyridine / dichloromethane / 0 - 20 °C / Inert atmosphere
2.1: triethylsilane; iodine / dichloromethane / 1 h / 0 °C / Inert atmosphere
2.2: 1 h / 0 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1.1: acetic anhydride; pyridine / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere
1.2: 72 h / -20 °C
2.1: triethylsilane; iodine / dichloromethane / 1 h / 0 °C / Inert atmosphere
2.2: 1 h / 0 - 20 °C / Inert atmosphere
View Scheme
trans 5-chloro-1,3-oxathiolane-2-carboxylic acid menthyl ester

trans 5-chloro-1,3-oxathiolane-2-carboxylic acid menthyl ester

2-trimethylsilyloxy-4-trimethylsilylamino-5-fluoropyrimidine
111878-21-8

2-trimethylsilyloxy-4-trimethylsilylamino-5-fluoropyrimidine

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate
764659-72-5

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate

Conditions
ConditionsYield
With triethylamine at 75℃; for 7h;15.42 g
(-)-menthol
2216-51-5

(-)-menthol

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate
764659-72-5

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: dichloro-acetic acid; dmap; dicyclohexyl-carbodiimide / hexane / 8 h / -5 - 100 °C
2.1: tetrabutylammomium bromide / water / 5 h / 95 °C
3.1: acetic acid / toluene / 100 °C / Inert atmosphere
3.2: 2 h / 20 - 80 °C
4.1: bis(trichloromethyl) carbonate; pyridine / dichloromethane / 6 h / -5 - 25 °C
5.1: triethylamine / 7 h / 75 °C
View Scheme
(1R,2S,5R)-(-)-menthyl dichloroacetate
21758-30-5

(1R,2S,5R)-(-)-menthyl dichloroacetate

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate
764659-72-5

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: tetrabutylammomium bromide / water / 5 h / 95 °C
2.1: acetic acid / toluene / 100 °C / Inert atmosphere
2.2: 2 h / 20 - 80 °C
3.1: bis(trichloromethyl) carbonate; pyridine / dichloromethane / 6 h / -5 - 25 °C
4.1: triethylamine / 7 h / 75 °C
View Scheme
L-menthyl glyoxylate
26315-61-7

L-menthyl glyoxylate

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate
764659-72-5

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: acetic acid / toluene / 100 °C / Inert atmosphere
1.2: 2 h / 20 - 80 °C
2.1: bis(trichloromethyl) carbonate; pyridine / dichloromethane / 6 h / -5 - 25 °C
3.1: triethylamine / 7 h / 75 °C
View Scheme
(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate
764659-72-5

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate

emtricitabine
143491-57-0

emtricitabine

Conditions
ConditionsYield
With sodium tetrahydroborate; dipotassium hydrogenphosphate; water; sodium hydroxide In ethanol at 20℃; Temperature;70%
Stage #1: (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathiolane-2-carboxylate With sodium tetrahydroborate In methanol at -5℃; for 5h; Inert atmosphere;
Stage #2: With isopropyl alcohol In water at 60℃; for 1h;
Stage #3: With methanol In water Product distribution / selectivity;
65%
With methanol; sodium tetrahydroborate at -7 - -5℃; for 6h; Product distribution / selectivity; Inert atmosphere;65%
(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate
764659-72-5

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate

2',3'-dideoxy-5-fluoro-3'-thiacytidine hydrochloride
258832-61-0

2',3'-dideoxy-5-fluoro-3'-thiacytidine hydrochloride

Conditions
ConditionsYield
Stage #1: (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathiolane-2-carboxylate With dipotassium hydrogenphosphate; water In ethanol at 15 - 20℃; for 1.16667h;
Stage #2: With sodium hydroxide; sodium tetrahydroborate In ethanol; water at 18 - 22℃; for 4h;
Stage #3: With hydrogenchloride In water pH=6 - 6.5;
(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate
764659-72-5

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate

succinic acid
110-15-6

succinic acid

lamivudine succinic acid
1235712-39-6

lamivudine succinic acid

Conditions
ConditionsYield
Stage #1: (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathiolane-2-carboxylate With sodium tetrahydroborate; dipotassium hydrogenphosphate; water; sodium hydroxide In methanol; ethanol at 12 - 20℃; for 3h;
Stage #2: succinic acid In water at 20℃; for 10h;
(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate
764659-72-5

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate

o-fluoro-benzoic acid
445-29-4

o-fluoro-benzoic acid

4-amino-5-fluoro-1-((2R,5S)-2-hydroxymethyl-[1,3]oxathiolane-5-yl)-1H-pyrimidin-2-one 2-fluorobenzoic acid salt
1321928-76-0

4-amino-5-fluoro-1-((2R,5S)-2-hydroxymethyl-[1,3]oxathiolane-5-yl)-1H-pyrimidin-2-one 2-fluorobenzoic acid salt

Conditions
ConditionsYield
Stage #1: (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathiolane-2-carboxylate With sodium tetrahydroborate; dipotassium hydrogenphosphate; sodium hydroxide In industrially methylated spirit; water at 18 - 22℃; for 4h;
Stage #2: o-fluoro-benzoic acid In water at 22 - 42℃;
(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate
764659-72-5

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate

C18H26FN3O4S*ClH

C18H26FN3O4S*ClH

Conditions
ConditionsYield
Stage #1: (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathiolane-2-carboxylate With sodium tetrahydroborate; potassium dihydrogenphosphate; sodium hydroxide In ethanol; water at 10 - 30℃;
Stage #2: With hydrogenchloride In ethanol; water for 0.5h; pH=4 - 5;

764659-72-5Relevant articles and documents

Synthesis of (±)-Emtricitabine and (±)-Lamivudine by Chlorotrimethylsilane-Sodium Iodide-Promoted Vorbrüggen Glycosylation

Jamison, Timothy F.,Mear, Sarah Jane,Nguyen, Long V.,Rochford, Ashley J.

, (2022/02/07)

By simple combination of water and sodium iodide (NaI) with chlorotrimethylsilane (TMSCl), promotion of a Vorbrüggen glycosylation en route to essential HIV drugs emtricitabine (FTC) and lamivudine (3TC) is achieved. TMSCl-NaI in wet solvent (0.1 M water)

PROCESS FOR PRODUCING LAMIVUDINE AND EMTRICITABINE

-

Page/Page column 19; 20; 21; 22, (2018/01/20)

This invention provides for flow and batch synthesis processes for the production of Lamivudine and Emtricitabine, including flow and batch synthesis processes wherein at least of the synthesis steps are conducted in a solvent free environment.

Preparation method for emtricitabine hydrohalide

-

Paragraph 0048; 0049; 0050, (2017/08/27)

The invention discloses a preparation method for emtricitabine hydrohalide. The preparation method for the emtricitabine hydrohalide provided by the invention comprises the following steps: subjecting crude emtricitabine and hydrogen halide to a salt-forming reaction in an alcohol solvent so as to obtain emtricitabine hydrohalide, wherein the HPLC purity of the crude emtricitabine is larger than 85%; the hydrogen halide is selected from the group consisting of hydrogen chloride, hydrogen bromide or hydrogen iodide; and X is selected from the group consisting of chlorine, bromine or iodine. The preparation method provided by the invention has the advantages of simple operation, simple and convenient postprocessing and high yield; and the prepared emtricitabine product has high purity, can reach standards of raw medicines, has an HPLC purity larger than 99.60% and a largest single impurity less than 0.10%, is low in production cost, and is applicable to industrial production.

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