methyl 3,5-di-O-toluoyl-2-deoxy-D-ribofuranose
2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride
Conditions | Yield |
---|---|
With acetyl chloride In acetic acid at 20℃; | 79% |
With hydrogenchloride In acetic acid at 10℃; for 1h; | 72% |
With hydrogenchloride; acetic acid In 1,4-dioxane | 70% |
1-O-methyl-2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythro-pentofuranose
2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride
Conditions | Yield |
---|---|
With hydrogenchloride In diethyl ether at 0℃; for 0.166667h; | 72% |
4-methyl-benzoyl chloride
2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride
Conditions | Yield |
---|---|
Stage #1: D-2-deoxyribose With acetyl chloride In methanol at 20℃; for 1.16667h; Inert atmosphere; Stage #2: 4-methyl-benzoyl chloride With pyridine In methanol at 0 - 20℃; Inert atmosphere; Stage #3: With acetic acid; acetyl chloride In methanol at 0℃; Inert atmosphere; | 36% |
1-O-methyl-2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranose
2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride
Conditions | Yield |
---|---|
With hydrogenchloride; acetic acid |
2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: AcCl / 2 h / 20 °C 1.2: DMAP; pyridine / 12 h / 0 °C 2.1: 72 percent / HCl gas / diethyl ether / 0.17 h / 0 °C View Scheme | |
Multi-step reaction with 3 steps 1: 96 percent / hydrogen chloride / 2 h 2: 85 percent / pyridine / 20 °C 3: 72 percent / HCl / acetic acid / 1 h / 10 °C View Scheme | |
Multi-step reaction with 3 steps 1: hydrogenchloride / 0.42 h / 20 °C 2: pyridine / 0 - 20 °C / Inert atmosphere 3: hydrogenchloride; acetic acid View Scheme |
4-methyl-benzoyl chloride
2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: AcCl / 2 h / 20 °C 1.2: DMAP; pyridine / 12 h / 0 °C 2.1: 72 percent / HCl gas / diethyl ether / 0.17 h / 0 °C View Scheme |
p-methylbenzoic anhydride
2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 90 percent / NaH / tetrahydrofuran / 4 h / 60 - 70 °C 2: HCl / diethyl ether View Scheme |
4-methyl-benzoyl chloride
2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 80 percent / Et3N / acetone 2: HCl / diethyl ether View Scheme | |
Multi-step reaction with 3 steps 1: Et3N; H2O / acetone / 2 h 2: 90 percent / NaH / tetrahydrofuran / 4 h / 60 - 70 °C 3: HCl / diethyl ether View Scheme |
1-O-methyl-2-deoxy-D-ribofuranoside
2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 80 percent / Et3N / acetone 2: HCl / diethyl ether View Scheme | |
Multi-step reaction with 2 steps 1: 85 percent / pyridine / 20 °C 2: 72 percent / HCl / acetic acid / 1 h / 10 °C View Scheme | |
Multi-step reaction with 2 steps 1: pyridine / Ambient temperature 2: HCl View Scheme |
2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: HCl / 0.42 h / Ambient temperature 2: pyridine / Ambient temperature 3: HCl View Scheme |
2-deoxy-D-ribose
2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: acetyl chloride / 0.5 h / 5 - 10 °C 1.2: 5 h / 5 - 10 °C 2.1: dmap; triethylamine / toluene / 2 h / 25 - 30 °C 3.1: hydrogenchloride; acetyl chloride; acetic acid / 1,4-dioxane; chloroform / 3.25 h / 10 - 15 °C View Scheme |
2-chloro-6-(2-pentylimidazol-1-yl)purine
2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride
2-chloro-9-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-6-(2-pentylimidazol-1-yl)purine
Conditions | Yield |
---|---|
With sodium hydride In dichloromethane; acetonitrile at 0 - 20℃; for 22h; | 100% |
2-chloro-6-(4,5-diphenylimidazol-1-yl)purine
2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride
Conditions | Yield |
---|---|
With sodium hydride In dichloromethane; acetonitrile at 0 - 20℃; for 22h; | 100% |
Stage #1: 2-chloro-6-(4,5-diphenylimidazol-1-yl)purine With sodium hydride In acetonitrile at 20℃; for 8h; Stage #2: 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride In dichloromethane; acetonitrile at 0℃; for 22h; | 100% |
2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride
Conditions | Yield |
---|---|
With sodium hydride In dichloromethane; acetonitrile at 0 - 20℃; for 22h; | 100% |
2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride
5-Cyclohexyl-2,4-bis-trimethylsilanyloxy-pyrimidine
C31H34N2O7
Conditions | Yield |
---|---|
In chloroform Ambient temperature; | 99% |
2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride
Conditions | Yield |
---|---|
With sodium hydride In dichloromethane; acetonitrile at 0 - 20℃; for 22h; | 99% |
4,6-difluoro-1H-indole
2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride
1-[2'-deoxy-3',5'-bis-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl]-4,6-difluoroindole
Conditions | Yield |
---|---|
With sodium hydride In acetonitrile at 20℃; for 0.333333h; | 99% |
With sodium hydride In acetonitrile for 0.333333h; | 99% |
7-fluoro-1H-indole
2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride
1-[2'-deoxy-3',5'-bis-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl]-7-fluoroindole
Conditions | Yield |
---|---|
With sodium hydride In acetonitrile at 20℃; for 0.333333h; | 99% |
With sodium hydride In acetonitrile for 0.333333h; | 99% |
3-(2-cyanovinyl)carbazole
2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride
C36H30N2O5
Conditions | Yield |
---|---|
Stage #1: 3-(2-cyanovinyl)carbazole With potassium hydroxide; Tris(3,6-dioxaheptyl)amine In acetonitrile at 20℃; for 0.5h; Stage #2: 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride In acetonitrile at 20℃; for 1h; | 99% |
2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride
5-tert-butyl-2,4-bis-trimethylsilanyloxy-pyrimidine
C29H32N2O7
Conditions | Yield |
---|---|
In chloroform Ambient temperature; | 98% |
4-cyanoindole
2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride
Conditions | Yield |
---|---|
Stage #1: 4-cyanoindole With sodium hydride In acetonitrile; mineral oil at 20℃; for 0.5h; Stage #2: 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride In acetonitrile; mineral oil at 20℃; for 5.5h; | 98% |
Stage #1: 4-cyanoindole With sodium hydride In acetonitrile; mineral oil at 20℃; for 0.5h; Inert atmosphere; Stage #2: 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride In acetonitrile; mineral oil at 20℃; Inert atmosphere; | 72% |
2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride
5-Cyclopentyl-2,4-bis-trimethylsilanyloxy-pyrimidine
C30H32N2O7
Conditions | Yield |
---|---|
In chloroform Ambient temperature; | 96% |
indole
2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride
1-(2-deoxy-3,5-di-O-p-toluyl-β-D-ribofuranosyl)indole
Conditions | Yield |
---|---|
With sodium hydride In acetonitrile for 0.333333h; | 95% |
With sodium hydride In acetonitrile at 0℃; | 73% |
With sodium hydride In acetonitrile at 20℃; for 24h; | 54% |
2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride
dibutyl 1H-imidazole-4,5-dicarboxylate
butyl 1-(2'-deoxy-3',5'-di-O-p-toluoyl-β-D-erythropentofuranosyl)-4,5-imidazoledicarboxylate
Conditions | Yield |
---|---|
With sodium hydride In acetonitrile at 20℃; for 3h; | 95% |
2-chloro-6-(2-propylimidazol-1-yl)purine
2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride
2-chloro-9-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-6-(2-propylimidazol-1-yl)purine
Conditions | Yield |
---|---|
With sodium hydride In dichloromethane; acetonitrile at 0 - 20℃; for 5h; | 95% |
2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride
2-trimethylsilylthio-4-trimethylsilyloxypyrimidine
1-(2'-deoxy-3',5'-di-O-(p-toluoyl)-β-D-erythro-ribofuranosyl)-2-thiouracil
Conditions | Yield |
---|---|
With tin(IV) chloride In 1,2-dichloro-ethane at -40℃; | 94% |
With tin(IV) chloride In various solvent(s) at -40℃; for 6.5h; Mechanism; var. solvents, var. temperat.; | 93.9% |
With tin(IV) chloride In various solvent(s) at -40℃; for 6.5h; | 93.9% |
4-fluoroindole
2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride
1-[2'-deoxy-3',5'-bis-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl]-4-fluoroindole
Conditions | Yield |
---|---|
With sodium hydride In acetonitrile at 20℃; for 0.333333h; | 94% |
With sodium hydride In acetonitrile for 0.333333h; | 94% |
6-fluoro-1H-indole
2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride
1-[2'-deoxy-3',5'-bis-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl]-6-fluoroindole
Conditions | Yield |
---|---|
With sodium hydride In acetonitrile at 20℃; for 0.333333h; | 94% |
With sodium hydride In acetonitrile for 0.333333h; | 93% |
C19H23N5O2
2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride
A
C40H43N5O7
Conditions | Yield |
---|---|
Stage #1: C19H23N5O2 With sodium hydride In acetonitrile at 25℃; Inert atmosphere; Stage #2: 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride In acetonitrile at 25℃; for 2h; Inert atmosphere; regioselective reaction; | A 94% B n/a C n/a |
2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride
5-cyclopropyl-2,4-bis(trimethylsilyloxy)pyrimidine
5-cyclopropyl-1-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythropentofuranosyl]uracil
Conditions | Yield |
---|---|
In chloroform Ambient temperature; | 92% |
5-fluoro-1H-indole
2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride
1-[2'-deoxy-3',5'-bis-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl]-5-fluoroindole
Conditions | Yield |
---|---|
With sodium hydride In acetonitrile at 20℃; for 0.333333h; | 92% |
With sodium hydride In acetonitrile for 0.333333h; | 92% |
Stage #1: 5-fluoro-1H-indole With sodium hydride In acetonitrile at 20℃; for 0.5h; Metallation; Stage #2: 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride for 2h; Substitution; |
2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride
2,5,6-trichloroindole
1-[2-deoxy-3,5-bis-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl]-2,5,6-trichloroindole
Conditions | Yield |
---|---|
Stage #1: 2,5,6-trichloroindole With sodium hydride In acetonitrile at 20℃; for 0.166667h; Metallation; Stage #2: 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride In acetonitrile for 0.333333h; Glycosylation; Further stages.; | 92% |
2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride
2-benzylthio-5,6-dichloroindole
2-benzylthio-1-[2-deoxy-3,5-bis-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl]-5,6-dichloroindole
Conditions | Yield |
---|---|
Stage #1: 2-benzylthio-5,6-dichloroindole With sodium hydride In acetonitrile at 20℃; for 0.166667h; Metallation; Stage #2: 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride In acetonitrile for 0.333333h; Glycosylation; Further stages.; | 92% |
ethynylmagnesium chloride
2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 3h; Inert atmosphere; | 92% |
5,6-dichlorobenzimidazole
2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride
Conditions | Yield |
---|---|
Stage #1: 5,6-dichlorobenzimidazole With sodium hydride In acetonitrile at 0 - 20℃; for 1h; Stage #2: 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride In acetonitrile at 0 - 20℃; for 2h; | 92% |
2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride
4-chloro-1H-pyrimido[4,5-b]indole
4-chloro-7-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-7H-pyrimido-[4,5-b]indole
Conditions | Yield |
---|---|
Stage #1: 4-chloro-1H-pyrimido[4,5-b]indole With sodium hydride In acetonitrile for 0.166667h; Heating; Stage #2: 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride In acetonitrile at 20℃; for 1h; | 91% |
dimethyl 2-bromo-1H-imidazole-4,5-dicarboxylate
2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride
2-bromo-1-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythropentofuranosyl)imidazole-4,5-dicarboxylic acid dimethyl ester
Conditions | Yield |
---|---|
With Proton Sponge In acetonitrile at 20℃; for 3h; | 91% |
2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride
4,6-dichloro-1H-pyrrolo<3,2-c>pyridine
4,6-Dichloro-1-<2-deoxy-3,5-bis-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl>-1H-pyrrolo<3,2-c>pyridine
Conditions | Yield |
---|---|
With potassium hydroxide; cryptand TDA-1 In acetonitrile for 0.75h; Ambient temperature; | 90% |
With sodium hydride 1.) acetonitrile, r.t., 30 min; 2.) 50 deg C, 2 h; Yield given. Multistep reaction; |
2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride
(2R,3S)-5β-azido-2-{[(4-methylbenzoyl)oxy]methyl}tetrahydrofuran-3-yl 4-methylbenzoate
Conditions | Yield |
---|---|
With cesium azide In dimethyl sulfoxide | 90% |
With potassium azide In dimethyl sulfoxide at 20℃; for 1h; Substitution; |
2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride
4-(3-tert-butoxycarbonylamino-propylcarbamoyl)-1H-pyrrole-3-carboxylic acid ethyl ester
4-(3-tert-butoxycarbonylamino-propylcarbamoyl)-1-[4-(4-methyl-benzoyloxy)-5-(4-methyl-benzoyloxymethyl)-tetrahydro-furan-2-yl]-1H-pyrrole-3-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With sodium hydride In acetonitrile | 90% |
4,5,6,7-tetrafluoro-1H-indole
2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride
Conditions | Yield |
---|---|
Stage #1: 4,5,6,7-tetrafluoro-1H-indole With sodium hydride In acetonitrile for 0.5h; Stage #2: 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride In acetonitrile at -5℃; for 1h; | 90% |
The α-D-erythro-Pentofuranosylchloride, 2-deoxy-, 3,5-bis(4-methylbenzoate), with the CAS registry number 4330-21-6, is also known as 2-Deoxy-3,5-bis-O-(4-methylbenzoyl)-α-D-erythro-pentofuranosyl chloride. It belongs to the product categories of Carbohydrates; Carbohydrates A to; Carbohydrates D-F Biochemicals and Reagents; Monosaccharide. Its EINECS registry number is 224-367-3. This chemical's molecular formula is C21H21ClO5 and molecular weight is 388.84. What's more, its IUPAC name is called [(2R,3S,5R)-5-Chloro-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate.
Physical properties about α-D-erythro-Pentofuranosylchloride, 2-deoxy-, 3,5-bis(4-methylbenzoate) are: (1)ACD/LogP: 5.23; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5.23; (4)ACD/LogD (pH 7.4): 5.23; (5)ACD/BCF (pH 5.5): 5523.34; (6)ACD/BCF (pH 7.4): 5523.34; (7)ACD/KOC (pH 5.5): 16605.81; (8)ACD/KOC (pH 7.4): 16605.81; (9)#H bond acceptors: 5; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 7; (12)Polar Surface Area: 61.83 Å2; (13)Index of Refraction: 1.583; (14)Molar Refractivity: 101.3 cm3; (15)Molar Volume: 302.9 cm3; (16)Surface Tension: 50.8 dyne/cm; (17)Density: 1.28 g/cm3; (18)Flash Point: 185.6 °C; (19)Enthalpy of Vaporization: 79.09 kJ/mol; (20)Boiling Point: 518.4 °C at 760 mmHg; (21)Vapour Pressure: 7.5E-11 mmHg at 25 °C.
When you are dealing with this chemical, you should be very careful. This chemical is irritating to eyes, respiratory system and skin. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1) SMILES: O=C(O[C@@H]1[C@H](O[C@H](Cl)C1)COC(=O)c2ccc(cc2)C)c3ccc(cc3)C
(2) InChI: InChI=1/C21H21ClO5/c1-13-3-7-15(8-4-13)20(23)25-12-18-17(11-19(22)26-18)27-21(24)16-9-5-14(2)6-10-16/h3-10,17-19H,11-12H2,1-2H3/t17-,18+,19-/m0/s1
(3) InChIKey: FJHSYOMVMMNQJQ-OTWHNJEPBB
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