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CAS No.: | 84414-90-4 |
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Name: | 1-(2,3-DIDEOXY-A-D-GLYCERO-PENT-2-ENOFURANOSYL)THYMINE |
Article Data: | 4 |
Molecular Structure: | |
Formula: | C10H12N2O4 |
Molecular Weight: | 224.216 |
Synonyms: | 1-(2,3-DIDEOXY-A-D-GLYCERO-PENT-2-ENOFURANOSYL)THYMINE;(2S-trans)-1-[2,5-Dihydro-5-(hydroxymethyl)-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione |
Density: | 1.374±0.06 g/cm3 (20 ºC 760 Torr) |
PSA: | 84.32000 |
LogP: | -0.70910 |
1-((2S,3R,5S)-3-Bromo-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione
A
1-(2,5-anhydro-3-deoxy-α-D-threo-pentofuranosyl)thymine
B
1-(2,3-dideoxy-α-D-glycero-pent-2-enofuranosyl)thymine
Conditions | Yield |
---|---|
With methanol; sodium methylate for 30h; Heating; | A 50% B 20% |
A
1-(2,3-dideoxy-α-D-glycero-pent-2-enofuranosyl)thymine
B
stavudin
Conditions | Yield |
---|---|
With Dowex R 50W; hydrogen cation In methanol Yield given. Yields of byproduct given; |
1-(2,3-dideoxy-α-D-glycero-pent-2-enofuranosyl)thymine
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: conc. HCl / dimethylformamide / Ambient temperature 2: 91 percent / imidazole / CH2Cl2 3: pyridine 4: DBU 5: 8 percent / NBS, 2,4-(trimethylsilyloxy)-6-methyl-pyrimidine, mol sieves 4A / CH2Cl2 / 0 °C 6: Dowex R 50W, H(1+) form / methanol View Scheme | |
Multi-step reaction with 6 steps 1: conc. HCl / dimethylformamide / Ambient temperature 2: 91 percent / imidazole / CH2Cl2 3: pyridine 4: DBU 5: 83 percent / NBS, mol. sieves 4A / CH2Cl2 / -78 °C 6: Dowex R 50W, H(1+) form / methanol View Scheme | |
Multi-step reaction with 6 steps 1: conc. HCl / Ambient temperature 2: 91 percent / imidazole / CH2Cl2 3: pyridine 4: DBU 5: 8 percent / NBS, 2,4-(trimethylsilyloxy)-6-methyl-pyrimidine, mol sieves 4A / CH2Cl2 / 0 °C 6: Dowex R 50W, H(1+) form / methanol View Scheme | |
Multi-step reaction with 6 steps 1: conc. HCl / Ambient temperature 2: 91 percent / imidazole / CH2Cl2 3: pyridine 4: DBU 5: 83 percent / NBS, mol. sieves 4A / CH2Cl2 / -78 °C 6: Dowex R 50W, H(1+) form / methanol View Scheme |
phenyl 2-deoxy-1-thio-D-erythro-pentofuranoside
1-(2,3-dideoxy-α-D-glycero-pent-2-enofuranosyl)thymine
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 91 percent / imidazole / CH2Cl2 2: pyridine 3: DBU 4: 8 percent / NBS, 2,4-(trimethylsilyloxy)-6-methyl-pyrimidine, mol sieves 4A / CH2Cl2 / 0 °C 5: Dowex R 50W, H(1+) form / methanol View Scheme | |
Multi-step reaction with 5 steps 1: 91 percent / imidazole / CH2Cl2 2: pyridine 3: DBU 4: 83 percent / NBS, mol. sieves 4A / CH2Cl2 / -78 °C 5: Dowex R 50W, H(1+) form / methanol View Scheme |
(2R,3S)-5-Phenylsulfanyl-2-trityloxymethyl-tetrahydro-furan-3-ol
1-(2,3-dideoxy-α-D-glycero-pent-2-enofuranosyl)thymine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: pyridine 2: DBU 3: 8 percent / NBS, 2,4-(trimethylsilyloxy)-6-methyl-pyrimidine, mol sieves 4A / CH2Cl2 / 0 °C 4: Dowex R 50W, H(1+) form / methanol View Scheme | |
Multi-step reaction with 4 steps 1: pyridine 2: DBU 3: 83 percent / NBS, mol. sieves 4A / CH2Cl2 / -78 °C 4: Dowex R 50W, H(1+) form / methanol View Scheme |
1-(2,3-dideoxy-α-D-glycero-pent-2-enofuranosyl)thymine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: DBU 2: 8 percent / NBS, 2,4-(trimethylsilyloxy)-6-methyl-pyrimidine, mol sieves 4A / CH2Cl2 / 0 °C 3: Dowex R 50W, H(1+) form / methanol View Scheme | |
Multi-step reaction with 3 steps 1: DBU 2: 83 percent / NBS, mol. sieves 4A / CH2Cl2 / -78 °C 3: Dowex R 50W, H(1+) form / methanol View Scheme |
(S)-2-Phenylsulfanyl-5-trityloxymethyl-2,5-dihydro-furan
1-(2,3-dideoxy-α-D-glycero-pent-2-enofuranosyl)thymine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 8 percent / NBS, 2,4-(trimethylsilyloxy)-6-methyl-pyrimidine, mol sieves 4A / CH2Cl2 / 0 °C 2: Dowex R 50W, H(1+) form / methanol View Scheme | |
Multi-step reaction with 2 steps 1: 83 percent / NBS, mol. sieves 4A / CH2Cl2 / -78 °C 2: Dowex R 50W, H(1+) form / methanol View Scheme |
1-(2,3-dideoxy-α-D-glycero-pent-2-enofuranosyl)thymine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 72 percent / NBS, mol. sieves 4A / CH2Cl2 / -78 °C 2: Dowex R 50W, H(1+) form / methanol View Scheme |
1-(2,3-dideoxy-α-D-glycero-pent-2-enofuranosyl)thymine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 98 percent / NBS, mol. sieves 4A / CH2Cl2 / -78 °C 2: Dowex R 50W, H(1+) form / methanol View Scheme |
2,4-bis(trimethylsiloxy)-5-methylpyrimidine
1-(2,3-dideoxy-α-D-glycero-pent-2-enofuranosyl)thymine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 83 percent / NBS, mol. sieves 4A / CH2Cl2 / -78 °C 2: Dowex R 50W, H(1+) form / methanol View Scheme | |
Multi-step reaction with 2 steps 1: 72 percent / NBS, mol. sieves 4A / CH2Cl2 / -78 °C 2: Dowex R 50W, H(1+) form / methanol View Scheme | |
Multi-step reaction with 2 steps 1: 98 percent / NBS, mol. sieves 4A / CH2Cl2 / -78 °C 2: Dowex R 50W, H(1+) form / methanol View Scheme |