2-Deoxy-2,2-difluoro-D-ribofuranose-3,5-dibenzoate-1-methanesulfonate

Product Name: 2-Deoxy-2,2-difluoro-D-ribofuranose-3,5-dibenzoate-1-methanesulfonate
CAS No.: 134877-42-2
Chemical Name: 2-Deoxy-2,2-difluoro-D-ribofuranose-3,5-dibenzoate-1-methanesulfonate
Synonyms: T8;2-Deoxy-2,2-difluoro-alpha-D-erythro-pentofuranose 3,5-dibenzoate 1-Methanesulfonate;Gemcitabine impurity 2/2-Deoxy-2,2-difluoro-3,5-dibenzoate-1-methanesulfonate α-D-erythro-Pentofuranose;Ly-2;Ly-B;Lyt2;Ly-35;Lyt-2;-3-(Benzoyloxy);((2R,3R,5R)-3-(benzoyloxy)-
CBNumber: CB01075243
Molecular Formula: C20H18F2O8S
Formula Weight: 456.41
MOL File: 134877-42-2.mol

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2-Deoxy-2,2-difluoro-D-ribofuranose-3,5-dibenzoate-1-methanesulfonate Property

Boiling point:: 588.4±50.0 °C(Predicted)
Density: 1.46
storage temp.: 2-8°C
Appearance: White to off-white Solid

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

TRC

Product number: D232725
Product name: 2-Deoxy-2,2-difluoro-3,5-dibenzoate-1-methanesulfonateα-D-erythro-Pentofuranose
Packaging: 25mg
Price: $45
Updated: 2021/12/16

TRC

Product number: D232725
Product name: 2-Deoxy-2,2-difluoro-3,5-dibenzoate-1-methanesulfonateα-D-erythro-Pentofuranose
Packaging: 50mg
Price: $70
Updated: 2021/12/16

TRC

Product number: D232725
Product name: 2-Deoxy-2,2-difluoro-3,5-dibenzoate-1-methanesulfonateα-D-erythro-Pentofuranose
Packaging: 100mg
Price: $105
Updated: 2021/12/16

Biosynth Carbosynth

Product number: MD71568
Product name: 3,5-Di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-a-D-ribofuranoside - 75% alpha purity
Packaging: 25g
Price: $50
Updated: 2021/12/16

Biosynth Carbosynth

Product number: MD71568
Product name: 3,5-Di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-a-D-ribofuranoside - 75% alpha purity
Packaging: 50g
Price: $90
Updated: 2021/12/16

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2-Deoxy-2,2-difluoro-D-ribofuranose-3,5-dibenzoate-1-methanesulfonate Chemical Properties,Usage,Production

Uses

2-Deoxy-2,2-difluoro-3,5-dibenzoate-1-methanesulfonate α-D-erythro-Pentofuranose is an impurity of Gemcitabine (G305028), a potential anticancer agent.

Synthesis

124-63-0

1173824-58-2

134877-42-2

((2R,3R)-3-(Benzoyloxy)-4,4-difluoro-5-hydroxytetrahydrofuran-2-yl)methyl benzoate (4.14 g, 10.9 mmol) was dissolved in anhydrous dichloromethane (52 mL), anhydrous triethylamine (2.4 mL) was added and the solution was cooled to 0 °C. Methylsulfonyl chloride (1.23 mL, 15.8 mmol) was added slowly and dropwise with stirring. The reaction mixture was stirred at room temperature for 18 hours. Upon completion of the reaction, the mixture was transferred to a partition funnel and partitioned with methylene chloride (140 mL) and saturated sodium bicarbonate solution (56 mL). The organic phase was separated, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give an oily product as a mixture of isoheads (5.03 g, quantitative yield). The chemical shifts were analyzed by 19F NMR (CDCl3, 471 MHz) and were δ -107.770, -108.22, -120.65, -121.17, -122.21, -122.73, -123.76, -124.45.1H NMR (CDCl3, 500 MHz) data of the main isocaprolite (60%): δ 8.13-8.04 (m, 4H, benzoyl), 7.65-7.54 (m, 2H, benzoyl), 7.50-7.41 (m, 4H, benzoyl), 6.17 (d, J=5.6 Hz, 1H, H-1), 5.62 (dd, J1=4.2 Hz, J2=16.4 Hz, 1H, H-3), 4.91 (q, J= 3.9 Hz, 1H, H-4), 4.81-4.61 (m, 2H, H-5), 3.17 (s, 3H, CH3). 1H NMR (CDCl3, 500MHz) data of the minor isohead (40%): δ 8.13-8.04 (4H, m, benzoyl), 7.65-7.54 (m, 2H, benzoyl), 7.50-7.41 (m, 4H, benzoyl), 6.09 (d, J=6.4Hz, 1H, H-1), 5.98 (dt, J1 = 7.3 Hz, J2=15.0 Hz, 1H, H-3), 4.81-4.61 (m, 3H, H-4, H-5), 3.03 (s, 3H, CH3).13C NMR (CDCl3, 126 MHz) data: δ 40.09, 40.20 (CH3), 62.52, 63.08 (C-5), 69.61 (dd ), 71.04 (dd, J1C-F=15.7 Hz, J2C-F=26.0 Hz, C-3), 79.68, 79.75, 82.59 (C-4), 98.81 (dd, J1C-F=25.0 Hz, J2C-F=41.8 Hz, C-1), 99.52 (dd, J1C-F=25.0 Hz, J2C-F=41.8 Hz, C-1), 99.52 (dd, J1C-F=25.0 Hz, J2C-F=41.8 Hz C-1), 99.52 (dd, J1C-F=24.5Hz, J2C-F=46.3Hz, C-1), 120.61 (dd, J1C-F=253.5Hz, J2C-F=269.8Hz, C-2), 120.91 (dd, J1C-F=249.3Hz, J2C-F=276.3Hz, C-2) , 128.42, 128.58, 128.63, 128.70, 128.76, 128.79 (benzene ring), 129.18, 129.25 ('ipso' benzene ring), 129.76, 130.07, 130.14, 133.51, 133.63, 134.19, 134.26 (benzene ring), 164.89 , 165.03, 165.81, 165.90 (carbonyl).

References

[1] Synthesis, 1992, # 6, p. 565 - 570
[2] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 14, p. 4338 - 4345
[3] Patent: WO2009/61781, 2009, A1. Location in patent: Page/Page column 102-103
[4] Biochemistry, 2010, vol. 49, # 7, p. 1404 - 1417
[5] Patent: WO2005/95430, 2005, A1. Location in patent: Page/Page column 18

2-Deoxy-2,2-difluoro-D-ribofuranose-3,5-dibenzoate-1-methanesulfonate Preparation Products And Raw materials

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View Lastest Price from 2-Deoxy-2,2-difluoro-D-ribofuranose-3,5-dibenzoate-1-methanesulfonate manufacturers

Career Henan Chemical Co

Product: 2-Deoxy-2,2-difluoro-D-ribofuranose-3,5-dibenzoate-1-methanesulfonate 134877-42-2
Price: US $7.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 100KG
Release date: 2019-08-29

134877-42-2, 2-Deoxy-2,2-difluoro-D-ribofuranose-3,5-dibenzoate-1-methanesulfonateRelated Search:

Deoxyribonuclease DEOXYRIBONUCLEIC ACID SODIUM SALT 3Epigemcitabine Cytosine Gemcitabine Impurity 21 2-Deoxy-2,2-difluoro-D-erythro-pentafuranous-1-ulose-3,5-dibenzoate b-D-ribofuranose, 2-deoxy-2,2-difluoro- Gemcitabine hydrochloride (R)-(+)-2,2-Dimethyl-1,3-dioxolane-4-carboxaldehyde Ethyl 3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-difluoro-3-hydroxypropionate 4-Amino-1-(2-deoxy-2,2-difluoro-a-D-erythro-pentofuranosyl)-2(1H)-pyrimidinone Hydrochloride Gemcitabine Impurity 10 Gemcitabine Impurity 12 α-D-erythro-Pentofuranose-2-deoxy-2,2-difluoro-3,5-dibenzoate DnaseⅠ DNA, SINGLE STRANDED, IMM. ON CELLULOSE, FROM CALF THYMUS* methanesulfonate 2-Deoxy-2,2-difluoro-D-ribofuranose-3,5-dibenzoate-1-methanesulfonate

T8

((2R,3R,5R)-3-(benzoyloxy)-

Gemcitabine impurity 2/2-Deoxy-2,2-difluoro-3,5-dibenzoate-1-methanesulfonate α-D-erythro-Pentofuranose

2-Deoxy-2,2-difluoro-alpha-D-erythro-pentofuranose 3,5-dibenzoate 1-Methanesulfonate

((2R,3R,5S)-3-(Benzoyloxy)-4,4-difluoro-5-((methyl-sulfonyl)oxy)tetrahydrofuran-2-yl)methyl benzo

-3-(Benzoyloxy)

-4,4-difluoro-5-((methylsulfonyl)

((2R,3R,5S)-3-(Benzoyloxy)-4,4-difluoro-5-((methyl-sulfonyl)oxy)tetrahydrofuran-2-yl)methyl be

2-Deoxy-2,2-difluoro-D-ribofuranose-3,5-dibenzoate-1-methanesulfonate

((2R,3R,5R)-3-(Benzoyloxy)-4,4-difluoro-5-((Methylsulfonyl)oxy)tetrahydrofuran-2-yl)Methyl benzoate

((2R,3R,5S)-3-(benzoyloxy)-4,4-difluoro-5-((Methylsulfonyl)oxy)tetrahydrofuran-2-yl)Methyl benzoate

3,5-Di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-a-D-ribofuranoside - 75% alpha purity

3,5-Di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-a-D-ribofuranoside - 98% alpha purity

3,5-Bis(benzoyl)-1-methanesulfonyloxy-2-deoxy-2,2-difluororibose(α-form)

2-Deoxy-2,2-difluoro-3,5-dibenzoate-1-methanesulfonate α-D-erythro-Pentofuranose

3,5-Bis(benzoyl)-1-methanesulfonyloxy-2-deoxy-2,2-difluorori...

134877-42-2 2-Deoxy-2,2-difluoro-D-ribofuranose-3,5-dibenzoate-1-methanesulfonate

α-D-erythro-Pentofuranose, 2-deoxy-2,2-difluoro-, 3,5-dibenzoate 1-methanesulfonate

alpha-2-deoxy-2,2-difluoro-D-ribofuranose-3,5-dibenzoate-1-methanesulfonate

3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-α-D-ribofuranoside

2-Deoxy-2,2-difluoro-D-ribofuranosyl-3,5-dibenzoyl-1-methanesulfonate

Ly-2

Ly-35

Ly-B

Lyt2

Lyt-2

134877-42-2

1211-11-9

122-11-9

C20H18O8SF2

Antineoplastic drug, difluorine nucleoside analog