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ChemicalBook >> CAS DataBase List >>2-Deoxy-2,2-difluoro-D-ribofuranose-3,5-dibenzoate-1-methanesulfonate

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
Molecular Weight:
456.41
MDL Number:
MFCD09842850
MOL File:
134877-42-2.mol
MSDS File:
SDS
Last updated:2025-07-24 18:13:42
Product description Number Pack Size Price
3,5-Di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-a-D-ribofuranoside - 75% alpha purity MD71568 50g $150
3,5-Di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-a-D-ribofuranoside - 75% alpha purity MD71568 25g $150
3,5-Di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-a-D-ribofuranoside - 75% alpha purity MD71568 100g $155
3,5-Di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-a-D-ribofuranoside - 98% alpha purity MD08302 5g $172.35
3,5-Di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-a-D-ribofuranoside - 75% alpha purity MD71568 250g $310
More product size

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

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

2-Deoxy-2,2-difluoro-D-ribofuranose-3,5-dibenzoate-1-methanesulfonate price More Price(59)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Biosynth MD71568 3,5-Di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-a-D-ribofuranoside - 75% alpha purity 134877-42-2 50g $150 2026-06-04 Buy
Biosynth MD71568 3,5-Di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-a-D-ribofuranoside - 75% alpha purity 134877-42-2 25g $150 2026-06-04 Buy
Biosynth MD71568 3,5-Di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-a-D-ribofuranoside - 75% alpha purity 134877-42-2 100g $155 2026-06-04 Buy
Biosynth MD08302 3,5-Di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-a-D-ribofuranoside - 98% alpha purity 134877-42-2 5g $172.35 2026-06-04 Buy
Biosynth MD71568 3,5-Di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-a-D-ribofuranoside - 75% alpha purity 134877-42-2 250g $310 2026-06-04 Buy
Product number Packaging Price Buy
MD71568 50g $150 Buy
MD71568 25g $150 Buy
MD71568 100g $155 Buy
MD08302 5g $172.35 Buy
MD71568 250g $310 Buy

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

Methanesulfonyl chloride

124-63-0

2-deoxy-2,2-difluoro-D-erythro-Pentofuranose-3,5-dibenzoate

1173824-58-2

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

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

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

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2-Deoxy-2,2-difluoro-D-ribofuranose-3,5-dibenzoate-1-methanesulfonate pictures 2019-08-30 2-Deoxy-2,2-difluoro-D-ribofuranose-3,5-dibenzoate-1-methanesulfonate
134877-42-2
$7.00 1KG 99% 100KG Career Henan Chemical Co
((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 ((2R,3R,5R)-3-(benzoyloxy)- 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 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 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 T8 134877-42-2 1211-11-9 122-11-9 C20H18O8SF2 Antineoplastic drug, difluorine nucleoside analog
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