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CAS No.: | 4330-21-6 |
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Name: | 2-Deoxy-alpha-D-erythropentofuranosyl chloride 3,5-bis(4-methylbenzoate) |
Article Data: | 30 |
Molecular Structure: | |
Formula: | C21H21ClO5 |
Molecular Weight: | 388.848 |
Synonyms: | D-erythro-Pentofuranosylchloride, 2-deoxy-, di-p-toluate, α- (8CI);p-Toluic acid, diester with2-deoxy-α-D-erythro-pentofuranosylchloride (8CI);1-Chloro-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;Hoffer's α-chlorosugar;NSC 148837; |
EINECS: | 224-367-3 |
Density: | 1.28 g/cm3 |
Melting Point: | 117-119 °C |
Boiling Point: | 518.414 °C at 760 mmHg |
Flash Point: | 185.58 °C |
Hazard Symbols: | Xi |
Risk Codes: | 36/37/38 |
Safety: | 26-36 |
PSA: | 27.69000 |
LogP: | 4.48360 |
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 |
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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