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CAS No.: | 63593-03-3 |
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Name: | 3-O-BENZYL-4-(HYDROXYMETHYL-1,2-O-ISOPROPYLIDENE)-ALPHA-D-ERYTHROPENTOFURANOSE |
Article Data: | 9 |
Molecular Structure: | |
Formula: | C16H22 O6 |
Molecular Weight: | 310.347 |
Synonyms: | Furo[2,3-d]-1,3-dioxole,a-D-erythro-pentofuranose deriv. |
Density: | 1.29 |
Boiling Point: | 442.5±45.0 °C(Predicted) |
PSA: | 77.38000 |
LogP: | 0.80300 |
formaldehyd
3-O-benzyl-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose
1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
Conditions | Yield |
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With sodium hydroxide In 1,4-dioxane Cannizzaro reaction; | 94% |
With sodium hydroxide In 1,4-dioxane at 28 - 30℃; for 16.83h; | 75% |
With sodium hydroxide In tetrahydrofuran; water at 20℃; | 47% |
With sodium hydroxide In tetrahydrofuran; water at 0 - 20℃; | 47% |
With sodium tetrahydroborate In tetrahydrofuran; water at 20℃; | 52.5 g |
1,2 5,6-O-di(isopropylidene)-α-D-allofuranose
1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose
1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
Conditions | Yield |
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Multi-step reaction with 2 steps 1: aq. NaIO4 / methanol 2: 94 percent / aq. NaOH / dioxane View Scheme | |
Multi-step reaction with 2 steps 1: sodium periodate / water / 1 h / 0 °C 2: sodium hydroxide / water; 1,4-dioxane / 144 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: sodium periodate / water; tetrahydrofuran / 1.5 h / 10 °C / Large scale 2: sodium hydroxide / 1,4-dioxane / 16.83 h / 28 - 30 °C View Scheme |
1,2:5,6-di-O-isopropylidene-3-O-benzyl-α-D-allofuranose
1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
Conditions | Yield |
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Multi-step reaction with 3 steps 1: aq. HCl / ethanol 2: aq. NaIO4 / methanol 3: 94 percent / aq. NaOH / dioxane View Scheme | |
Multi-step reaction with 3 steps 1: acetic acid / water / 72 h / 20 °C 2: sodium periodate / water / 1 h / 0 °C 3: sodium hydroxide / water; 1,4-dioxane / 144 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: acetic acid / water / 20 - 25 °C / Large scale 2: sodium periodate / water; tetrahydrofuran / 1.5 h / 10 °C / Large scale 3: sodium hydroxide / 1,4-dioxane / 16.83 h / 28 - 30 °C View Scheme |
formaldehyd
1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
Conditions | Yield |
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With sodium hydroxide In 1,4-dioxane; water at 0 - 20℃; for 144h; | 77 g |
Diacetone D-glucose
1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
Conditions | Yield |
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Multi-step reaction with 4 steps 1.1: sodium hydride / mineral oil; acetonitrile / 1 h / 0 °C / Inert atmosphere 1.2: 4.5 h / 0 °C 2.1: acetic acid / water / 72 h / 20 °C 3.1: sodium periodate / water / 1 h / 0 °C 4.1: sodium hydroxide / water; 1,4-dioxane / 144 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 4 steps 1: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / toluene / 4 h / 30 - 90 °C / Large scale 2: acetic acid / water / 20 - 25 °C / Large scale 3: sodium periodate / water; tetrahydrofuran / 1.5 h / 10 °C / Large scale 4: sodium hydroxide / 1,4-dioxane / 16.83 h / 28 - 30 °C View Scheme |
benzyl bromide
1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
Conditions | Yield |
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Multi-step reaction with 4 steps 1.1: sodium hydride / mineral oil; acetonitrile / 1 h / 0 °C / Inert atmosphere 1.2: 4.5 h / 0 °C 2.1: acetic acid / water / 72 h / 20 °C 3.1: sodium periodate / water / 1 h / 0 °C 4.1: sodium hydroxide / water; 1,4-dioxane / 144 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 0 - 20 °C 2.1: acetic acid; water / 20 °C 3.1: sodium periodate / water; methanol / 1 h / 20 °C 4.1: sodium tetrahydroborate / water; tetrahydrofuran / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 0 - 20 °C 2.1: acetic acid / water / 20 °C 3.1: sodium periodate / water; methanol / 1 h / 20 °C 4.1: sodium hydroxide / water; tetrahydrofuran / 0 - 20 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 0 - 20 °C 2.1: acetic acid / water / 20 °C 3.1: sodium periodate / methanol; water / 1 h / 20 °C 4.1: sodium hydroxide / tetrahydrofuran; water / 20 °C View Scheme |
3-O-benzyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose
1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
Conditions | Yield |
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Multi-step reaction with 3 steps 1: acetic acid; water / 20 °C 2: sodium periodate / water; methanol / 1 h / 20 °C 3: sodium tetrahydroborate / water; tetrahydrofuran / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: acetic acid / water / 20 °C 2: sodium periodate / water; methanol / 1 h / 20 °C 3: sodium hydroxide / water; tetrahydrofuran / 0 - 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: acetic acid / water / 20 °C 2: sodium periodate / methanol; water / 1 h / 20 °C 3: sodium hydroxide / tetrahydrofuran; water / 20 °C View Scheme |
1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
Conditions | Yield |
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Multi-step reaction with 2 steps 1: sodium periodate / water; methanol / 1 h / 20 °C 2: sodium tetrahydroborate / water; tetrahydrofuran / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: sodium periodate / water; methanol / 1 h / 20 °C 2: sodium hydroxide / water; tetrahydrofuran / 0 - 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: sodium periodate / methanol; water / 1 h / 20 °C 2: sodium hydroxide / tetrahydrofuran; water / 20 °C View Scheme |
D-glucofuranose
1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
Conditions | Yield |
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Multi-step reaction with 7 steps 1: zinc(II) chloride; phosphoric acid / 15 - 30 °C / Large scale 2: potassium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite; sodium hydrogencarbonate / water; ethyl acetate / 0 - 35 °C 3: sodium tetrahydroborate / water / 10 - 15 °C 4: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / toluene / 4 h / 30 - 90 °C / Large scale 5: acetic acid / water / 20 - 25 °C / Large scale 6: sodium periodate / water; tetrahydrofuran / 1.5 h / 10 °C / Large scale 7: sodium hydroxide / 1,4-dioxane / 16.83 h / 28 - 30 °C View Scheme |