ChemicalBook > CAS DataBase List > ((2R,3R,4R)-3-(benzoyloxy)-4-fluoro-4-methyl-5-oxotetrahydrofuran-2-yl)methyl benzoate

((2R,3R,4R)-3-(benzoyloxy)-4-fluoro-4-methyl-5-oxotetrahydrofuran-2-yl)methyl benzoate

Product Name
((2R,3R,4R)-3-(benzoyloxy)-4-fluoro-4-methyl-5-oxotetrahydrofuran-2-yl)methyl benzoate
CAS No.
874638-80-9
Chemical Name
((2R,3R,4R)-3-(benzoyloxy)-4-fluoro-4-methyl-5-oxotetrahydrofuran-2-yl)methyl benzoate
Synonyms
(2R)-2-DEOXY-2-FLUORO-2-METHYL-D-ERYTHRO;((2R,3S,4R)-3-(benzoyloxy)-4-fluoro-4-methyl-5-oxotetrahydrofuran-2-yl)methyl benzoate;(S)-isopropyl 2-(((S)-(((2R,3R,4R,5S)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate;SFBM;SF-X1;Sofosbuvir INT 3;Sofosbuvir imp-2;PSI-6130 interMediate;Sofosbuvir Impurity 30;SofosBuvir Impurity 46
CBNumber
CB32514087
Molecular Formula
C20H17FO6
Formula Weight
372.35
MOL File
874638-80-9.mol
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((2R,3R,4R)-3-(benzoyloxy)-4-fluoro-4-methyl-5-oxotetrahydrofuran-2-yl)methyl benzoate Property

Melting point:
133℃
Boiling point:
458.6±34.0 °C(Predicted)
Density 
1.33
storage temp. 
2-8°C
Appearance
White to yellow Solid
InChI
InChI=1/C20H17FO6/c1-20(21)16(27-18(23)14-10-6-3-7-11-14)15(26-19(20)24)12-25-17(22)13-8-4-2-5-9-13/h2-11,15-16H,12H2,1H3/t15-,16-,20-/s3
InChIKey
OUKYMZJNLWKCSO-ZFVYKOPKNA-N
SMILES
C([C@H]1OC(=O)[C@@](F)(C)[C@@H]1OC(C1C=CC=CC=1)=O)OC(C1C=CC=CC=1)=O |&1:1,5,8,r|
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

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N-Bromosuccinimide Price

TRC
Product number
D232985
Product name
(2R)-2-Deoxy-2-fluoro-2-methyl-D-erythropentonicAcidγ-Lactone3,5-Dibenzoate
Packaging
25g
Price
$165
Updated
2021/12/16
TRC
Product number
D232985
Product name
(2R)-2-Deoxy-2-fluoro-2-methyl-D-erythropentonicAcidγ-Lactone3,5-Dibenzoate
Packaging
50g
Price
$275
Updated
2021/12/16
Usbiological
Product number
293138
Product name
3,5-Di-O-benzoyl-2-deoxy-2-fluoro-2C-methyl-D-ribono-1,4-lactone
Packaging
2g
Price
$319
Updated
2021/12/16
Biosynth Carbosynth
Product number
MD09387
Product name
3,5-Di-O-benzoyl-2-deoxy-2-fluoro-2C-methyl-D-ribono-1,4-lactone
Packaging
100g
Price
$410
Updated
2021/12/16
SynQuest Laboratories
Product number
2H23-3-13
Product name
((2R,3R,4R)-3-(Benzoyloxy)-4-fluoro-4-methyl-5-oxotetrahydrofuran-2-yl)methylbenzoate
Packaging
100g
Price
$295
Updated
2021/12/16
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((2R,3R,4R)-3-(benzoyloxy)-4-fluoro-4-methyl-5-oxotetrahydrofuran-2-yl)methyl benzoate Chemical Properties,Usage,Production

Uses

neuromuscular blocking agent

Uses

(2R)-2-Deoxy-2-fluoro-2-methyl-D-erythropentonic Acid γ-Lactone 3,5-Dibenzoate is a reactant used in the synthesis of 1''-C-cyano-2''-fluoro-2''-C-methyl pyrimidine nucleosides as HCV polymerase inhibitors.

Application

((2R,3R,4R)-3-(benzoyloxy)-4-fluoro-4-methyl-5-oxotetrahydrofuran-2-yl)methyl benzoate is an impurity of Sofosbuvir. Sofosbuvir is a NS5B inhibtor used for the treatment of hepatitis C. It is only recommended with some combination of ribavirin, peginterferon-alfa, simeprevir, ledipasvir or daclatasvir.

Synthesis

879551-04-9

98-88-4

874638-80-9

(3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one (60 mg, 0.16 mmol) was dissolved in anhydrous pyridine (1 mL) and benzoyl chloride (0.3 mL) was added slowly. The reaction mixture was stirred at room temperature for 20 min, then water (1 mL) was added and stirring was continued for 20 min. The reaction solution was diluted with ethyl acetate (5 mL) and washed sequentially with water (2 mL) and 1M HCl (2 mL x 3). The organic phase was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=10:1) to afford ((2R,3R,4R)-3-(benzyloxy)-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate (118 mg, 87% yield) as a white solid.1H NMR (CDCl3) δ (ppm): 8.08 (m, 2H. Ar-H), 7.99 (m, 2H, Ar-H), 7.63 (m, 1H, Ar-H), 7.58 (m, 1H, Ar-H), 7.49 (m, 2H, Ar-H), 7.43 (m, 2H, Ar-H), 5.51 (dd, 1H, J=7.2,17.6Hz, H-3), 5.00 (m, 1H, H-4). 4.78 (dd, 1H, J=3.6,12.8Hz, H-5), 4.59 (dd, 1H, J=5.2,12.8Hz, H-5'), 1.75 (d, 3H, J=23.6Hz, CH3-2).

References

[1] Patent: WO2006/31725, 2006, A2. Location in patent: Page/Page column 13; 30-31
[2] Patent: CN105418547, 2016, A. Location in patent: Paragraph 0019; 0020
[3] Patent: CN106146433, 2016, A. Location in patent: Paragraph 0009; 0025
[4] Patent: CN107573304, 2018, A. Location in patent: Paragraph 0120-0124
[5] Patent: WO2014/108525, 2014, A1. Location in patent: Page/Page column 18

((2R,3R,4R)-3-(benzoyloxy)-4-fluoro-4-methyl-5-oxotetrahydrofuran-2-yl)methyl benzoate Preparation Products And Raw materials

Raw materials

Preparation Products

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((2R,3R,4R)-3-(benzoyloxy)-4-fluoro-4-methyl-5-oxotetrahydrofuran-2-yl)methyl benzoate Suppliers

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View Lastest Price from ((2R,3R,4R)-3-(benzoyloxy)-4-fluoro-4-methyl-5-oxotetrahydrofuran-2-yl)methyl benzoate manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
((2R,3R,4R)-3-(benzoyloxy)-4-fluoro-4-methyl-5-oxotetrahydrofuran-2-yl)methyl benzoate 874638-80-9
Price
US $0.00-0.00/KG
Min. Order
100g
Purity
98%min
Supply Ability
100kgs
Release date
2021-08-30
Henan Aochuang Chemical Co.,Ltd.
Product
((2R,3R,4R)-3-(benzoyloxy)-4-fluoro-4-methyl-5-oxotetrahydrofuran-2-yl)methyl benzoate 874638-80-9
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
1Ton
Release date
2022-10-17
Henan Bao Enluo International TradeCo.，LTD
Product
((2R,3R,4R)-3-(benzoyloxy)-4-fluoro-4-methyl-5-oxotetrahydrofuran-2-yl)methyl benzoate 874638-80-9
Price
US $10.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
500t/month
Release date
2023-08-17

874638-80-9, ((2R,3R,4R)-3-(benzoyloxy)-4-fluoro-4-methyl-5-oxotetrahydrofuran-2-yl)methyl benzoateRelated Search:

D-Alanine, N-[[P(S),2'R]-2'-cyano-2'-deoxy-2'-Methyl-P-phenyl-5'-cytidylyl]-, 1-Methylethyl ester Cytidine,N-benzoyl-2^-C-Methyl-,3^,5^-dibenzoate(9CI) Sofosbuvir Impurity 17 L-Alanine, N-[(R)-(2,3,4,5,6-pentafluorophenoxy)phenoxyphosphinyl]-, 1-Methylethyl ester (3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxyMethyl)-3-Methyl-dihydrofuran-2(3H)-one N-[(S)-(2,3,4,5,6-pentafluorophenoxy)phenoxyphosphinyl]-L-alanine 1-Methylethyl ester L-Alanine isopropyl ester hydrochloride (2'R)-2'-Deoxy-2'-fluoro-2'-Methyl-uridine 3',5'-dibenzoate PSI-6130 derivative D-Arabinonic acid, 2-C-methyl-4,5-O-(1-methylethylidene)-,ethyl ester 2'-deoxy-2'-fluoro-2'-C-methyluridine Sofosbuvir alpha-D-erythro-Pentofuranous-2-ulose 1,3,5-tribenzoate sofosBuvir impurity 36 SofosBuvir Impurity 55 Sofosbuvir impurity E SofosBuvir Impurity 40 SofosBuvir Impurity 54

  • 3,5-di-O-benzoyl-2-deoxy-2-fluoro-D-ribono-γ-latone
  • SFBM
  • (2R)-2-Deoxy-2-fluoro-2-methyl-D-erythropentonic acid γ-lactone 3,5-dibenzoate
  • Sofosbuvir intermediate
  • Sofosbuvir Impurity 30
  • 3,5-Di-O-benzoyl-2-deoxy-2-fluoro-2C-methyl-D-ribono-1,4-lactone
  • (2R,3R,4R)-2-[(benzoyloxy)methyl]-4-fluoro-4-methyl-5-oxooxolan-3-yl benzoate
  • Sofosbuvir Intermediate 1
  • Sofosbuvir INT 3
  • ((2R,3S,4R)-3-(benzoyloxy)-4-fluoro-4-methyl-5-oxotetrahydrofuran-2-yl)methyl benzoate
  • ((2R,3R,4R)-3-(benzoyloxy)-4-fluoro-5-oxotetrahydrofuran-2-yl)methyl benzoate
  • (2R)-2-Deoxy-2-fluoro-2-methy-D- erythropentonic acid gamma-lactone 3,5- dibenzoate
  • nterMediate of Sofosbuvir
  • Di-O-benzoyl-2-deoxy-2-fluoro-2-C-Methyl-D
  • Sofosbuvir imp-2
  • 3,5-di-O-benzoyl-2-deoxy-2-fluoro-2-C-methyl-D-ribono-γ-latone
  • 4-amino-1-[(2R,3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyloxolan-2-yl]pyrimidin-2-one
  • (S)-isopropyl 2-(((S)-(((2R,3R,4R,5S)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
  • (2R)-2-Deoxy-2-fluoro-2-Methyl-D-erythro-pentonic acid-g-lactone 3,5-dibenzoate
  • Methyl ((2R,3R,4R)-3-(benzoyloxy)-4-fluoro-4-Methyl-5-oxotetrahydrofuran-2-yl) benzoate
  • (2R)-2-Deoxy-2-fluoro-2-methyl-D-erythropentonic acid gamma-lactone 3,5-dibenzoate
  • PSI-6130 interMediate
  • (2R)-2-DEOXY-2-FLUORO-2-METHYL-D-ERYTHRO
  • ((2R,3R,4R)-3-(benzoyloxy)-4-fluoro-4-methyl-5-oxotetrahydrofuran-2-yl)methyl benzoate
  • 3,5-Di-O-benzoyl-2-deoxy-2-fluoro-2-C-Methyl-D-ribono-γ-lactone
  • D-erythro-Pentonic acid, 2-deoxy-2-fluoro-2-Methyl-, γ-lactone, 3,5-dibenzoate, (2R)-
  • (2R)-2-Deoxy-2-fluoro-2-Methyl-D-erythropentonic acid
  • InterMediate of Sofosbuvir
  • 3. ((2R,3R,4R)-3-(benzoyloxy)-4-fluoro-4-Methyl-5-oxotetra
  • SofosBuvir Impurity 46
  • 3,5-Di-O-benzoyl-2-deoxy-2-fluoro-2C-methyl-D-arabino-1,4-lactone
  • (2R-3R,4R)-3-(Benzoyzxy)-4-Fluoro-4-Methyl-5-Oxotetrahydrofuran-2Yl)Methyl Benzoate
  • Sofosbuvir Impurity 101
  • SF-X1
  • ((2R,3R,4R)-3-(BENZOYLOXY)-4-FLUORO-4-METHYL-5-OXOTETRAHYDROFURAN-2-YL)METHYL BENZOATE 874638-80-9
  • ((2R,3R,4R)-3-(benzoyloxy)-4-fluoro-4-methyl-5-oxotetrahydrofuran-2-yl)methyl benzoate ISO 9001：2015 REACH
  • ((2R,3R,4R)-3-(DENZOYLOXY)-4-FLUORO-4-METHYL-5-OXOTETRAHYDROFURAN-2-YL)METHYL BENZOATE
  • ((2R,3R,4R)-3-(benzoyloxy)-4-fluoro-4-methyl-5-oxotetrahydro...
  • (2R,3R,4R)-3- (benzoyoxy)-4-fluoro-4-methyl-5-oxotetrahydrofuran-2yl)methyl Benzoate, 98%
  • (2R)-3,5-di-O-benzoyl-2-fluoro-2-C-methyl-D-ribono-r-lactone
  • (2R)-2-Deoxy-2-fluoro-2-methyl-D-erythropentonic acid γ-lactone 3,5-dibenzoate
  • (2R,3R,4R)-3-Benzoyloxy-4-fluoro-4-methyl-5-oxo-2-(benzoyloxymethyl)tetrahydrofuran
  • (2R) -2-Deoxy-2-Fluoro-2-Methyl-D-Erythropentonic Acid y-Lactone 3,5-Dibenzoate
  • 874638-80-9
  • 1334518-02-8
  • 874638-08-9
  • C20H17FO6
  • C20H17O6F
  • apis
  • Sofosbuvir intermediate