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

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

Product Name
2-Deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-dibenzoate-1-methanesulfonate
CAS No.
122111-11-9
Chemical Name
2-Deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-dibenzoate-1-methanesulfonate
Synonyms
GCTB-T8;ER-878898;acid(TES);Gemcitabine salt;GeMcitabine InterMediate 8;"2-Deoxy-2,2-difluoro-D-erythro-;((2R,3R)-3-(benzoyloxy)-4,4-difluoro;2-Deoxy-2,2-difluoro-D-erythro-pentofura...;2-DEXY-2,2-DIFLUORO-3,5-O-DIBENZOYLRIBOSE MESYLATE;D-erythro-Pentofuranose, 2-deoxy-2,2-difluoro-, 3,5-dibenzoate-1-
CBNumber
CB8187886
Molecular Formula
C20H18F2O8S
Formula Weight
456.41
MOL File
122111-11-9.mol
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2-Deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-dibenzoate-1-methanesulfonate Property

Melting point:
66-74°C
Boiling point:
588.4±50.0 °C(Predicted)
Density 
1.46±0.1 g/cm3(Predicted)
storage temp. 
2-8°C
solubility 
Chloroform, Methanol
form 
Solid
color 
Off-White to Pale Yellow
optical activity
96.07°(C=0.01g/ml CHCL3)
InChI
InChI=1S/C20H18F2O8S/c1-31(25,26)30-19-20(21,22)16(29-18(24)14-10-6-3-7-11-14)15(28-19)12-27-17(23)13-8-4-2-5-9-13/h2-11,15-16,19H,12H2,1H3/t15-,16-,19?/m1/s1
InChIKey
LIAQHZDWFACWFK-QNRNLVPOSA-N
SMILES
C1(OS(C)(=O)=O)O[C@H](COC(=O)C2=CC=CC=C2)[C@@H](OC(=O)C2=CC=CC=C2)C1(F)F
CAS DataBase Reference
122111-11-9(CAS DataBase Reference)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

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

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N-Bromosuccinimide Price

Usbiological
Product number
008073
Product name
2-Deoxy-2,2-difluoro-D-erythro-ribofuranose-3,5-dibenzoate 1-Methanesulfonate
Packaging
50mg
Price
$425
Updated
2021/12/16
TRC
Product number
D232790
Product name
2-Deoxy-2,2-difluoro-D-erythro-ribofuranose-3,5-dibenzoate1-Methanesulfonate
Packaging
500mg
Price
$1210
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
CRB0000194
Product name
2-DEOXY-2,2-DIFLUORO-D-ERYTHRO-RIBOFURANOSE-3,5-DIBENZOATE 1-METHANESULFONATE
Purity
95.00%
Packaging
500MG
Price
$1732.5
Updated
2021/12/16
AK Scientific
Product number
B651
Product name
2-Deoxy-2,2-difluoro-3,5-O-dibenzoylribosemesylate
Packaging
100g
Price
$717
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
CRB0000194
Product name
2-DEOXY-2,2-DIFLUORO-D-ERYTHRO-RIBOFURANOSE-3,5-DIBENZOATE 1-METHANESULFONATE
Purity
95.00%
Packaging
50MG
Price
$721.88
Updated
2021/12/16
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2-Deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-dibenzoate-1-methanesulfonate Chemical Properties,Usage,Production

Chemical Properties

Brown Liquid

Uses

Gemcitabine intermediate.

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. After completion of the reaction, the mixture was diluted with dichloromethane (140 mL) and washed with saturated sodium bicarbonate solution (56 mL). The organic phase was dried with anhydrous sodium sulfate and concentrated under reduced pressure to give an oily product as a mixture of isomers (5.03 g, quantitative yield). 19F NMR (CDCl3, 471 MHz): δ -107.70, -108.22, -120.65, -121.17, -122.21, -122.73, -123.76, -124.45. 1H NMR (CDCl3, 500 MHz) of the major isomer (60%): δ 8.13-8.04 (m, 4H, Bz), 7.65-7.54 (m, 2H, Bz), 7.50-7.41 (m, 4H, Bz), 6.17 (d, J = 5.6 Hz, 1H, H-1), 5.62 (dd, J1 = 4.2 Hz, J2 = 16.4 Hz), 5.62 (dd, J1 = 16.4 Hz, J2 = 16.4 Hz, J2 = 16.4 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, 500 MHz) of the secondary isomer (40%): δ 8.13-8.04 (m, 4H, Bz), 7.65-7.54 (m, 2H, Bz), 7.50-7.41 (m, 4H, Bz), 6.09 (d, J = 6.4 Hz, 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): δ 40.09, 40.20 (CH3), 62.52, 63.08 (C-5), 69.61 (dd, J1C-F = 15.7 Hz, J2C-F = 26.0 Hz, C-3), 71.04 (dd, J1C-F = 17.4 Hz, J2C-F = 36.4 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 = 24.5 Hz, J2C-F = 46.3 Hz, C-1), 120.61 (dd, J1C-F = 253.5 Hz, J2C-F = 269.8 Hz, C-2), 120.91 (dd, J1C-F = 249.3 Hz, J2C-F = 276.3 Hz, C-2), 128.42, 128.58, 128.63, 128.70, 128.76, 128.79 (Ph), 129.18, 129.25 ('ipso ' Ph), 129.76, 130.07, 130.14, 133.51, 133.63, 134.19, 134.26 (Ph), 164.89, 165.03, 165.81, 165.90 (CO).

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-erythro-pentofuranose-3,5-dibenzoate-1-methanesulfonate Preparation Products And Raw materials

Raw materials

Preparation Products

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

Canada 1 China 202 India 16 United Kingdom 2 United States 13 Global 234
Carbosynth Limited
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View Lastest Price from 2-Deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-dibenzoate-1-methanesulfonate manufacturers

Shanghai Joiny Pharmaceutical Co.,LTD
Product
2-Deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-dibenzoate-1-methanesulfonate 122111-11-9
Price
US $0.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
1 Ton
Release date
2022-12-09
Zhuozhou Wenxi import and Export Co., Ltd
Product
2-Deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-dibenzoate-1-methanesulfonate 122111-11-9
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-11
Zhuozhou Wenxi import and Export Co., Ltd
Product
2-Deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-dibenzoate-1-methanesulfonate 122111-11-9
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-09

122111-11-9, 2-Deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-dibenzoate-1-methanesulfonateRelated Search:

Pazufloxacin mesilate Imatinib Gabexate mesylate Levofloxacin Methylate Methyl methanesulfonate Trifluoromethanesulfonic acid N-Carboxybenzyl GeMcitabine Ethyl (3R,S)-2,2-difluoro-3-hydroxy-3-(2,2-dimethyldioxolan-4-yl)propionate 2-Deoxy-2,2-difluoro-D-erythro-pentafuranous-1-ulose-3,5-dibenzoate Gemcitabine Methanesulfonic acid α-D-erythro-Pentofuranose-2-deoxy-2,2-difluoro-3,5-dibenzoate 2-DEOXY-2-FLUORO-D-ARABINOFURANOSE 2-DEOXY-2,2-DIFLUORO-D-RIBOFURANOSE-3,5-DIBENZOATE-1-METHANESULFONATE 2-Deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-dibenzoate-1-methanesulfonate

  • D-ERYTHRO-PENTOFURANOSE, 2-DEOXY-2,2-DIFLUORO-, 3,5-DIBENZOATE 1-METHANESULFONATE
  • 2-deoxy-2,2-difluoro-d-erythro-pentofuranose-3,5-dibenzoate-1-methanesulfonate
  • 2-DEXY-2,2-DIFLUORO-3,5-O-DIBENZOYLRIBOSE MESYLATE
  • 2-Deoxy-2,2-difluoro-D-erythro-ribofuranose-3,5-dibenzoate 1-Methanesulfonate
  • GeMcitabine InterMediate 8
  • T8, 2-Deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-dibenzoate-1-Methanesulfonate
  • ((2R,3R)-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-D-ribofuranoside
  • benzoic acid (3-benzoyloxy-4,4-difluoro-5-methylsulfonyloxy-2-oxolanyl)methyl ester
  • 2-Deoxy-2,2-difluoro-D-erythro-pentofura...
  • ER-878898
  • D-erythro-Pentofuranose, 2-deoxy-2,2-difluoro-, 3,5-dibenzoate-1-
  • 2-Deoxy-2,2-difluoro-D- erythro –pentofuranose -3,5- dibenzoate-1- methanesulfonate (for Gemcitabine)
  • "2-Deoxy-2,2-difluoro-D-erythro-
  • ((2R,3R)-3-(benzoyloxy)-4,4-difluoro
  • 2-Deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-dibenzoate-1-methanesulfonate [G-8]
  • 2-Deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-dibenzoate-1-methanesulfonate ISO 9001：2015 REACH
  • 2-Deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-dibenzoate-1-methanes
  • GCTB-T8
  • (2R,3S)-3-Benzoyloxy-4,4-difluoro-5-methylsulfonyloxyoxolan-2-yl]methyl benzoate(95%)
  • (2R,3S)-3-Benzoyloxy-4,4-difluoro-5-methylsulfonyloxyoxolan-2-yl]methyl benzoate(75%)
  • 2-deoxy-2,2-difluoro-D-cathopentafurose-3,5-diphenylmethyl-1-methanesulfonate
  • 2-Deoxy-2,2-difluoro-D-erythro-pentafuranose-3-5-dibenzoate-1-methanesulfonate
  • 2-Deoxy-2,2-difluoro-D-ribofuranose-3,5-dibenzoate-1-methanesul phonate
  • 2-Deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-dibenzoate-1-methanesulfonate [T-8]
  • (2R,3R)-3-(Benzoyloxy)-4,4-difluoro-5-[(methylsulfonyl)oxy]-2-tetrahydrofuryl]methyl Benzoate
  • Gemcitabine salt
  • acid(TES)
  • 2-Deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-dibenzoate-1-methanesulfote
  • 122111-11-9
  • Aromatics Compounds
  • Aromatics
  • Carbohydrates & Derivatives
  • Intermediates