Product Name

  • Name

    2-Deoxy-2,2-difluoro-D-erythro-pentafuranous-1-ulose-3,5-dibenzoate

  • EINECS 601-822-8
  • CAS No. 122111-01-7
  • Article Data8
  • CAS DataBase
  • Density 1.41 g/cm3
  • Solubility
  • Melting Point 117-119 °C(lit.)
  • Formula C19H14F2O6
  • Boiling Point 437.216 °C at 760 mmHg
  • Molecular Weight 376.313
  • Flash Point 210.499 °C
  • Transport Information
  • Appearance off-white solid
  • Safety 24/25
  • Risk Codes
  • Molecular Structure Molecular Structure of 122111-01-7 (2-Deoxy-2,2-difluoro-D-erythro-pentafuranous-1-ulose-3,5-dibenzoate)
  • Hazard Symbols
  • Synonyms 2-Deoxy-2,2-difluoro-D-erythro-pentafuranous-1-ulose-3,5-dibenzoate 98%;(2R,3R)-4,4-Difluor-5-oxo-2-{[(phenylcarbonyl)oxy]methyl}tetrahydrofuran-3-ylbenzolcarboxylat (non-preferred name);[(2R,3R)-3-(Benzoyloxy)-4,4-difluoro-5-oxotetrahydrofuran-2-yl]methyl benzoate;[(2R,3R)-3-(Benzoyloxy)-4,4-difluoro-5-oxotetrahydrofuran-2-yl]methyl benzoate (non-preferred name);2-Deoxy-2,2-difluoro-D-erythro-pentonic acid g-lactone 3,5-dibenzoate;
  • PSA 78.90000
  • LogP 2.62970

Synthetic route

benzoyl chloride
98-88-4

benzoyl chloride

2-deoxy-2,2-difluoro-1-carbonylribose
95058-77-8

2-deoxy-2,2-difluoro-1-carbonylribose

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate
122111-01-7

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate

Conditions
ConditionsYield
With pyridine; dmap In dichloromethane for 1.5h; Reflux;67%
With pyridine; dmap In ethyl acetate at 20℃; for 12h; Reflux;58.3 g
With pyridine In dichloromethane at 0 - 20℃; for 0.666667h;
With pyridine; dmap at 30 - 50℃; for 8h; Inert atmosphere; Large scale;
2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate

C19H16F2O7
866473-33-8

C19H16F2O7

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate
122111-01-7

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate

Conditions
ConditionsYield
toluene-4-sulfonic acid In toluene Product distribution / selectivity; Heating / reflux; Dean and Stark apparatus;34%
C5H6F2O4

C5H6F2O4

benzoyl chloride
98-88-4

benzoyl chloride

2-deoxy-2,2-difluoro-1-carbonylribose
95058-77-8

2-deoxy-2,2-difluoro-1-carbonylribose

A

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate

B

C19H16F2O7
866473-33-8

C19H16F2O7

C

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate
122111-01-7

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate

Conditions
ConditionsYield
With pyridine; dmap In ethyl acetate at 60 - 65℃; for 6h; Product distribution / selectivity;
...Expand
C19H16F2O7

C19H16F2O7

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate
122111-01-7

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate

Conditions
ConditionsYield
toluene-4-sulfonic acid In toluene Product distribution / selectivity; Heating / reflux; Dean and Stark apparatus;
pyridine
110-86-1

pyridine

benzoyl chloride
98-88-4

benzoyl chloride

2-deoxy-2,2-difluoro-1-carbonylribose
95058-77-8

2-deoxy-2,2-difluoro-1-carbonylribose

A

pyridine hydrochloride
628-13-7

pyridine hydrochloride

B

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate
122111-01-7

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate

Conditions
ConditionsYield
With dmap In ethyl acetate at 60 - 65℃; for 6.25h;
...Expand
ethyl 2-deoxy-2,2-difluoro-D-erythro,D-threo-pentonate
114420-06-3

ethyl 2-deoxy-2,2-difluoro-D-erythro,D-threo-pentonate

benzoyl chloride
98-88-4

benzoyl chloride

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate
122111-01-7

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate

Conditions
ConditionsYield
Stage #1: ethyl 2-deoxy-2,2-difluoro-D-erythro,D-threo-pentonate; toluene-4-sulfonic acid In water at 75 - 80℃; for 3h;
Stage #2: benzoyl chloride With pyridine; dmap In ethyl acetate at 60 - 65℃; for 3h; Product distribution / selectivity; Dean and Stark apparatus;
2-deoxy-2,2-difluoropentofuranos-1-ulose

2-deoxy-2,2-difluoropentofuranos-1-ulose

benzoyl chloride
98-88-4

benzoyl chloride

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate
122111-01-7

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate

Conditions
ConditionsYield
With pyridine In ethyl acetate at 25 - 60℃; Inert atmosphere;
benzoyl chloride
98-88-4

benzoyl chloride

ethyl (3R,S)-2,2-difluoro-3-hydroxy-(2,2-dimethyldioxolpent-4-yl)propionate
928797-50-6

ethyl (3R,S)-2,2-difluoro-3-hydroxy-(2,2-dimethyldioxolpent-4-yl)propionate

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate
122111-01-7

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate

Conditions
ConditionsYield
Stage #1: ethyl (3R,S)-2,2-difluoro-3-hydroxy-(2,2-dimethyldioxolpent-4-yl)propionate With water; pyridinium trifluroacetate In water; acetonitrile for 3h; Heating / reflux;
Stage #2: benzoyl chloride With pyridine; dmap In ethyl acetate at 0 - 65℃; for 10h; Product distribution / selectivity;
Stage #1: ethyl (3R,S)-2,2-difluoro-3-hydroxy-(2,2-dimethyldioxolpent-4-yl)propionate With water; pyridinium p-toluenesulfonate In water; acetonitrile for 12h; Heating / reflux;
Stage #2: benzoyl chloride With pyridine; dmap In ethyl acetate at 0 - 65℃; for 10h; Product distribution / selectivity;
C8H8F2O5

C8H8F2O5

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate
122111-01-7

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: acetic acid / chloroform / 2 h / 50 °C
2.1: sodium tetrahydroborate / tetrahydrofuran / 0.5 h
2.2: 2 h / 25 °C
3.1: pyridine; dmap / dichloromethane / 1.5 h / Reflux
View Scheme
ethyl (3R,S)-2,2-difluoro-3-hydroxy-(2,2-dimethyldioxolpent-4-yl)propionate
928797-50-6

ethyl (3R,S)-2,2-difluoro-3-hydroxy-(2,2-dimethyldioxolpent-4-yl)propionate

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate
122111-01-7

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride / water / 70 - 80 °C / Large scale
2: pyridine; dmap / 8 h / 30 - 50 °C / Inert atmosphere; Large scale
View Scheme
2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate
122111-01-7

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate

(2R,3R)-2-((benzoyloxy)methyl)-4,4-difluoro-5-hydroxyoxolan-3-yl benzoate
1173824-58-2

(2R,3R)-2-((benzoyloxy)methyl)-4,4-difluoro-5-hydroxyoxolan-3-yl benzoate

Conditions
ConditionsYield
With lithium tri-t-butoxyaluminum hydride In tetrahydrofuran; diethyl ether at 10 - 30℃; for 1h;100%
Stage #1: 2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate With sodium bis(2-methoxyethoxy)aluminium dihydride In tetrahydrofuran; toluene at -30℃; for 1h;
Stage #2: With hydrogenchloride In tetrahydrofuran; water; toluene		99.5%
With lithium tri-t-butoxyaluminum hydride In tetrahydrofuran; diethyl ether at -78℃; for 1h; Inert atmosphere;84%
2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate
122111-01-7

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate

Benzoic acid (2R,3R,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-4,4-difluoro-3-hydroxy-tetrahydro-furan-2-ylmethyl ester

Benzoic acid (2R,3R,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-4,4-difluoro-3-hydroxy-tetrahydro-furan-2-ylmethyl ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 100 percent / LiAl(OBu-t)3H / diethyl ether; tetrahydrofuran / 1 h / 10 - 30 °C
2: 100 percent / triethylamine / CH2Cl2 / 2 h / 23 °C
3: 1) Me3SiOTf / 1) 1,1,2-trichloroethane, r.t., 30 min, 2) 113 deg C, 18 h
4: ammonia / methanol
View Scheme
2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate
122111-01-7

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate

1-(2'-deoxy-2',2'-difluoro-3',5'-di-O-benzoyl-D-ribofuranosyl)-4-acetamidopyrimidin-2-one
143157-23-7, 143157-26-0

1-(2'-deoxy-2',2'-difluoro-3',5'-di-O-benzoyl-D-ribofuranosyl)-4-acetamidopyrimidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 100 percent / LiAl(OBu-t)3H / diethyl ether; tetrahydrofuran / 1 h / 10 - 30 °C
2: 100 percent / triethylamine / CH2Cl2 / 2 h / 23 °C
3: 1) Me3SiOTf / 1) 1,2-dichloroethane, 30 deg C, 1 h, 2) 1,2-dichloroethane, 83 deg C, overnight
View Scheme
2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate
122111-01-7

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate

2’-deoxy-2’,2’-difluoro-cytidine
103882-84-4

2’-deoxy-2’,2’-difluoro-cytidine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 100 percent / LiAl(OBu-t)3H / diethyl ether; tetrahydrofuran / 1 h / 10 - 30 °C
2: 100 percent / triethylamine / CH2Cl2 / 2 h / 23 °C
3: 1) Me3SiOTf / 1) 1,2-dichloroethane, 30 deg C, 1 h, 2) 1,2-dichloroethane, 83 deg C, overnight
4: 1.73 kg / ammonia (gas) / methanol / Ambient temperature
View Scheme
2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate
122111-01-7

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate

3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-D-erythro-pentofuranose
134877-42-2, 134877-43-3, 122111-11-9

3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-D-erythro-pentofuranose

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 100 percent / LiAl(OBu-t)3H / diethyl ether; tetrahydrofuran / 1 h / 10 - 30 °C
2: 100 percent / triethylamine / CH2Cl2 / 2 h / 23 °C
View Scheme
Multi-step reaction with 2 steps
1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran; diethyl ether / 1 h / -78 °C / Inert atmosphere
2: triethylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 2 h / -78 - 20 °C / Inert atmosphere
2: triethylamine / dichloromethane / 2 h / 0 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1: lithium tri-(tert-butoxy)aluminum hydride / tetrahydrofuran / 2 h / -78 - 20 °C / Inert atmosphere
2: triethylamine / tetrahydrofuran; dichloromethane / 2 h / 0 - 20 °C
View Scheme
2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate
122111-01-7

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate

C23H19F2N3O6
134790-40-2

C23H19F2N3O6

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 100 percent / LiAl(OBu-t)3H / diethyl ether; tetrahydrofuran / 1 h / 10 - 30 °C
2: 100 percent / triethylamine / CH2Cl2 / 2 h / 23 °C
3: 1) Me3SiOTf / 1) 1,1,2-trichloroethane, r.t., 30 min, 2) 113 deg C, 18 h
View Scheme
2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate
122111-01-7

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate

(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate
134790-39-9

(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 100 percent / LiAl(OBu-t)3H / diethyl ether; tetrahydrofuran / 1 h / 10 - 30 °C
2: 100 percent / triethylamine / CH2Cl2 / 2 h / 23 °C
3: 1) Me3SiOTf / 1) 1,1,2-trichloroethane, r.t., 30 min, 2) 113 deg C, 18 h
View Scheme
2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate
122111-01-7

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate

C19H16F2O7

C19H16F2O7

Conditions
ConditionsYield
With hydrogenchloride In water at 45 - 50℃; for 3h;
2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate
122111-01-7

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate

A

3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-D-β-ribofuranose

3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-D-β-ribofuranose

B

3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-D-α-ribofuranose

3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-D-α-ribofuranose

Conditions
ConditionsYield
Stage #1: 2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate With sodium bis(2-methoxyethoxy)aluminium dihydride In tetrahydrofuran; toluene at -70 - -50℃; for 1h;
Stage #2: With hydrogenchloride; methanol; water In tetrahydrofuran; toluene for 0.5h;
With lithium tri-t-butoxyaluminum hydride In tetrahydrofuran; diethyl ether at 20℃; for 1.5h; Inert atmosphere; Overall yield = 99.8 %; Overall yield = 10 g;A n/a
B n/a
With sodium tetrahydroborate; zinc(II) chloride; tert-butyl alcohol In tetrahydrofuran; ethyl acetate at 15℃; Overall yield = 100 %;
2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate
122111-01-7

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate

C19H15(3)HF2O6

C19H15(3)HF2O6

Conditions
ConditionsYield
Stage #1: 2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate With C10H22(3)HB In tetrahydrofuran at 0 - 20℃; for 17.5h; Inert atmosphere; Cooling with ice;
Stage #2: With water In tetrahydrofuran for 0.5h; Inert atmosphere; Reflux;
2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate
122111-01-7

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate

C19H15(2)HF2O6

C19H15(2)HF2O6

Conditions
ConditionsYield
Stage #1: 2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate With C10H22(2)HB In tetrahydrofuran at 0 - 20℃; for 17.5h; Inert atmosphere; Cooling with ice;
Stage #2: With water In tetrahydrofuran for 0.5h; Inert atmosphere; Reflux;
2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate
122111-01-7

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate

1-(2-deoxy-2,2-difluoro-β-D-erythro-pentofuranos-1-yl)-5-chlorouracil
132786-36-8

1-(2-deoxy-2,2-difluoro-β-D-erythro-pentofuranos-1-yl)-5-chlorouracil

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran; diethyl ether / 1 h / -78 °C / Inert atmosphere
2.1: triethylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere
3.1: trimethylsilyl trifluoromethanesulfonate / 1,1-dichloroethane / 10 h / 90 - 100 °C / Inert atmosphere
3.2: 20 °C
4.1: sodium methylate / methanol / 20 °C / Inert atmosphere
4.2: Amberlite
View Scheme
2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate
122111-01-7

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate

1-(2-deoxy-2,2-difluoro-β-D-erythro-pentofuranos-1-yl)thymine
95058-80-3

1-(2-deoxy-2,2-difluoro-β-D-erythro-pentofuranos-1-yl)thymine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran; diethyl ether / 1 h / -78 °C / Inert atmosphere
2.1: triethylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere
3.1: trimethylsilyl trifluoromethanesulfonate / 1,1-dichloroethane / 10 h / 90 - 100 °C / Inert atmosphere
3.2: 20 °C
4.1: sodium methylate / methanol / 20 °C / Inert atmosphere
4.2: Amberlite
View Scheme
2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate
122111-01-7

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate

C25H25F2IN3O9P
1321580-98-6

C25H25F2IN3O9P

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran; diethyl ether / 1 h / -78 °C / Inert atmosphere
2.1: triethylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere
3.1: trimethylsilyl trifluoromethanesulfonate / 1,1-dichloroethane / 10 h / 90 - 100 °C / Inert atmosphere
3.2: 20 °C
4.1: sodium methylate / methanol / 20 °C / Inert atmosphere
4.2: Amberlite
5.1: 1-methyl-1H-imidazole / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere
View Scheme
2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate
122111-01-7

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate

C19H21F2IN3O9P
1321581-00-3

C19H21F2IN3O9P

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran; diethyl ether / 1 h / -78 °C / Inert atmosphere
2.1: triethylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere
3.1: trimethylsilyl trifluoromethanesulfonate / 1,1-dichloroethane / 10 h / 90 - 100 °C / Inert atmosphere
3.2: 20 °C
4.1: sodium methylate / methanol / 20 °C / Inert atmosphere
4.2: Amberlite
5.1: 1-methyl-1H-imidazole / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere
View Scheme
2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate
122111-01-7

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate

C29H27F2IN3O9P
1321581-01-4

C29H27F2IN3O9P

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran; diethyl ether / 1 h / -78 °C / Inert atmosphere
2.1: triethylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere
3.1: trimethylsilyl trifluoromethanesulfonate / 1,1-dichloroethane / 10 h / 90 - 100 °C / Inert atmosphere
3.2: 20 °C
4.1: sodium methylate / methanol / 20 °C / Inert atmosphere
4.2: Amberlite
5.1: 1-methyl-1H-imidazole / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere
View Scheme
2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate
122111-01-7

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate

C23H23F2IN3O9P
1321581-02-5

C23H23F2IN3O9P

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran; diethyl ether / 1 h / -78 °C / Inert atmosphere
2.1: triethylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere
3.1: trimethylsilyl trifluoromethanesulfonate / 1,1-dichloroethane / 10 h / 90 - 100 °C / Inert atmosphere
3.2: 20 °C
4.1: sodium methylate / methanol / 20 °C / Inert atmosphere
4.2: Amberlite
5.1: 1-methyl-1H-imidazole / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere
View Scheme
2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate
122111-01-7

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate

C25H25BrF2N3O9P
1321581-03-6

C25H25BrF2N3O9P

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran; diethyl ether / 1 h / -78 °C / Inert atmosphere
2.1: triethylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere
3.1: trimethylsilyl trifluoromethanesulfonate / 1,1-dichloroethane / 10 h / 90 - 100 °C / Inert atmosphere
3.2: 20 °C
4.1: sodium methylate / methanol / 20 °C / Inert atmosphere
4.2: Amberlite
5.1: 1-methyl-1H-imidazole / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere
View Scheme
2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate
122111-01-7

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate

C25H25ClF2N3O9P
1321581-04-7

C25H25ClF2N3O9P

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran; diethyl ether / 1 h / -78 °C / Inert atmosphere
2.1: triethylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere
3.1: trimethylsilyl trifluoromethanesulfonate / 1,1-dichloroethane / 10 h / 90 - 100 °C / Inert atmosphere
3.2: 20 °C
4.1: sodium methylate / methanol / 20 °C / Inert atmosphere
4.2: Amberlite
5.1: 1-methyl-1H-imidazole / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere
View Scheme
2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate
122111-01-7

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate

1-(2-deoxy-2,2-difluoro-β-D-erythro-pentofuranos-1-yl)-5-iodouracil
132832-46-3

1-(2-deoxy-2,2-difluoro-β-D-erythro-pentofuranos-1-yl)-5-iodouracil

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran; diethyl ether / 1 h / -78 °C / Inert atmosphere
2.1: triethylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere
3.1: trimethylsilyl trifluoromethanesulfonate / 1,1-dichloroethane / 10 h / 90 - 100 °C / Inert atmosphere
3.2: 20 °C
4.1: sodium methylate / methanol / 20 °C / Inert atmosphere
4.2: Amberlite
View Scheme
2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate
122111-01-7

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate

1-(2-deoxy-2,2-difluoro-β-D-erythro-pentofuranos-1-yl)-5-bromouracil
132786-35-7

1-(2-deoxy-2,2-difluoro-β-D-erythro-pentofuranos-1-yl)-5-bromouracil

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran; diethyl ether / 1 h / -78 °C / Inert atmosphere
2.1: triethylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere
3.1: trimethylsilyl trifluoromethanesulfonate / 1,1-dichloroethane / 10 h / 90 - 100 °C / Inert atmosphere
3.2: 20 °C
4.1: sodium methylate / methanol / 20 °C / Inert atmosphere
4.2: Amberlite
View Scheme
2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate
122111-01-7

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate

A

1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-β-D-erythro-pentofuranos-1-yl)-5-iodouracil
1321580-93-1

1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-β-D-erythro-pentofuranos-1-yl)-5-iodouracil

B

1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-α-D-erythro-pentofuranos-1-yl)-5-iodouracil

1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-α-D-erythro-pentofuranos-1-yl)-5-iodouracil

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran; diethyl ether / 1 h / -78 °C / Inert atmosphere
2.1: triethylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere
3.1: trimethylsilyl trifluoromethanesulfonate / 1,1-dichloroethane / 10 h / 90 - 100 °C / Inert atmosphere
3.2: 20 °C
View Scheme

2-Deoxy-2,2-difluoro-D-erythro-pentafuranous-1-ulose-3,5-dibenzoate Chemical Properties

Molecular Structure of 2-Deoxy-2,2-difluoro-D-erythro-pentafuranous-1-ulose-3,5-dibenzoate (CAS NO.122111-01-7):

Empirical Formula: C19H14F2O6
Molecular Weight: 376.3077
H bond acceptors: 6
H bond donors: 0
Freely Rotating Bonds: 7
Polar Surface Area: 78.9Å2
Index of Refraction: 1.571
Molar Refractivity: 87.61 cm3
Molar Volume: 266.798 cm3
Surface Tension: 51.72 dyne/cm
Density: 1.41 g/cm3
Flash Point: 210.499 °C
Enthalpy of Vaporization: 69.38 kJ/mol
Boiling Point: 437.216 °C at 760 mmHg
Vapour Pressure: 0 mmHg at 25°C
Melting point: 117-119 °C(lit.)
Product Categories: Intermediatesofgemcitabine; 13C & 2H Sugars; Carbohydrates & Derivatives; Antineoplastic drug, difluorine nucleoside analog

2-Deoxy-2,2-difluoro-D-erythro-pentafuranous-1-ulose-3,5-dibenzoate Safety Profile

WGK Germany: 3

2-Deoxy-2,2-difluoro-D-erythro-pentafuranous-1-ulose-3,5-dibenzoate Specification

  2-Deoxy-2,2-difluoro-D-erythro-pentafuranous-1-ulose-3,5-dibenzoate , with CAS number of 122111-01-7, can be called (2R,3R)-4,4-Difluor-5-oxo-2-{[(phenylcarbonyl)oxy]methyl}tetrahydrofuran-3-ylbenzolcarboxylat (non-preferred name) ; (2R,3R)-4,4-Difluoro-5-oxo-2-{[(phenylcarbonyl)oxy]methyl}tetrahydrofuran-3-yl benzoate (non-preferred name) ; [(2R,3R)-3-(Benzoyloxy)-4,4-difluoro-5-oxotetrahydro-2-furanyl]methyl benzoate ; [(2R,3R)-3-(Benzoyloxy)-4,4-difluoro-5-oxotetrahydro-2-furanyl]methyl benzoate (non-preferred name) ; [(2R,3R)-3-(Benzoyloxy)-4,4-difluoro-5-oxotetrahydrofuran-2-yl]methyl benzoate ; [(2R,3R)-3-(Benzoyloxy)-4,4-difluoro-5-oxotetrahydrofuran-2-yl]methyl benzoate (non-preferred name) ; 2-Deoxy-2,2-difluoro-D-erythro-pentafuranous-1-ulose-3,5-dibenzoate 98% ; 2-Deoxy-2,2-difluoro-D-erythro-pentonic acid g-lactone 3,5-dibenzoate . It is an off-white solid.

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