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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

Raw materials

Preparation Products

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

China 94 Germany 1 India 8 United Kingdom 1 United States 9 Global 113
Service Chemical Inc.
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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