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CAS No.: | 109428-30-0 |
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Name: | 1,5:2,3-Dianhydro-4,6-O-benzylidene-D-allitol |
Molecular Structure: | |
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Formula: | C13H14 O4 |
Molecular Weight: | 234.252 |
Synonyms: | Allitol,1,5:2,3-dianhydro-4,6-O-benzylidene- (6CI) |
PSA: | 40.22000 |
LogP: | 1.26680 |
1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol
Conditions | Yield |
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Stage #1: (4aR,8aS)-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxine With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 1h; Stage #2: With dimethylsulfide for 0.166667h; | 38% |
1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol
Conditions | Yield |
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With sodium methylate In toluene at 50℃; Yield given; |
1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol
1,5-anhydro-2-azido-4,6-O-benzylidene-2-deoxy-D-altritol
Conditions | Yield |
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With sodium azide; ammonium chloride In 2-methoxy-ethanol; water at 100℃; for 18h; | 95% |
With sodium azide; ammonium chloride In 2-methoxy-ethanol; water at 100℃; for 18h; Inert atmosphere; | 95% |
uracil
1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol
1-((4aR,7R,8S,8aS)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-1H-pyrimidine-2,4-dione
Conditions | Yield |
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With sodium hydride In N,N-dimethyl-formamide at 120℃; | 69% |
Stage #1: uracil With sodium hydride In DMF (N,N-dimethyl-formamide) for 1h; Heating / reflux; Stage #2: 1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol In DMF (N,N-dimethyl-formamide) for 24h; Heating / reflux; | 29% |
allylmagnesium bromide
1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol
Conditions | Yield |
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Stage #1: allylmagnesium bromide With copper(l) iodide In tetrahydrofuran at -30℃; for 0.25h; Inert atmosphere; Stage #2: 1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol In tetrahydrofuran at -30℃; for 1.5h; Inert atmosphere; regioselective reaction; | 69% |
With copper(l) iodide In tetrahydrofuran at -30℃; for 1.5h; Inert atmosphere; | 69% |
1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol
(4aR,7R,8S,8aS)-7-(6-Amino-purin-9-yl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol
Conditions | Yield |
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With sodium hydride In N,N-dimethyl-formamide at 100℃; | 54% |
thymin
1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol
Conditions | Yield |
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Stage #1: thymin With sodium hydride In DMF (N,N-dimethyl-formamide) for 2h; Heating / reflux; Stage #2: 1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol In DMF (N,N-dimethyl-formamide) for 24h; Heating / reflux; | 47% |
2-azidoethanol
1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol
Conditions | Yield |
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Stage #1: 2-azidoethanol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Inert atmosphere; Stage #2: 1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol In N,N-dimethyl-formamide; mineral oil at 0 - 80℃; Inert atmosphere; | 45% |
5-iodouracil
1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol
Conditions | Yield |
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Stage #1: 5-iodouracil With sodium hydride In DMF (N,N-dimethyl-formamide) for 2h; Heating / reflux; Stage #2: 1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol In DMF (N,N-dimethyl-formamide) for 24h; Heating / reflux; | 20% |
6-chloropurine
1,5:2,3-anhydro-4,6-O-benzylidene-D-allitol
Conditions | Yield |
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With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 48h; | 16% |