1-(6,7,8-Trideoxy-2,3-O-isopropylidene-β-D-allo-oct-7-enofuranosyl)-3-(4-methoxybenzyl)uracil

Base Information

Chemical Name:1-(6,7,8-Trideoxy-2,3-O-isopropylidene-β-D-allo-oct-7-enofuranosyl)-3-(4-methoxybenzyl)uracil
CAS No.:121845-99-6
Molecular Formula:C₂₃H₂₈N₂O₇
Molecular Weight:444.485
Hs Code.:

Synonyms:1-(6,7,8-Trideoxy-2,3-O-isopropylidene-β-D-allo-oct-7-enofuranosyl)-3-(4-methoxybenzyl)uracil

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Chemical Property of 1-(6,7,8-Trideoxy-2,3-O-isopropylidene-β-D-allo-oct-7-enofuranosyl)-3-(4-methoxybenzyl)uracil

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Technology Process of 1-(6,7,8-Trideoxy-2,3-O-isopropylidene-β-D-allo-oct-7-enofuranosyl)-3-(4-methoxybenzyl)uracil

There total 5 articles about 1-(6,7,8-Trideoxy-2,3-O-isopropylidene-β-D-allo-oct-7-enofuranosyl)-3-(4-methoxybenzyl)uracil which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 67.0%

: 121845-98-5
(3aR,4S,6R,6aS)-6-(3-(4-methoxybenzyl)-3,4-dihydro-2,4-dioxopyrimidin-1(2H)-yl)-tetrahydro-2,2-dimethylfuro[3,4-d][1,3]dioxole-4-carbaldehyde

: 762-72-1
allyl-trimethyl-silane

: 121845-99-6
1-(6,7,8-Trideoxy-2,3-O-isopropylidene-β-D-allo-oct-7-enofuranosyl)-3-(4-methoxybenzyl)uracil

Guidance literature:: With boron trifluoride diethyl etherate; In various solvent(s); at -78 ℃; for 3h;
DOI:10.1021/ja00197a047

Reference yield:

: 362-43-6
2',3'-O-isopropylideneuridine

: 121845-99-6
1-(6,7,8-Trideoxy-2,3-O-isopropylidene-β-D-allo-oct-7-enofuranosyl)-3-(4-methoxybenzyl)uracil

Guidance literature:: Multi-step reaction with 5 steps

1: 100 percent / triethylamine / CH₂Cl₂ / 0.08 h / Ambient temperature

2: NaH / dimethylformamide / 0.17 h / 0 °C

3: K₂CO₃ / methanol / 2 h / Ambient temperature

4: 79 percent / dimethyl sulfoxide, trifluoroacetic acid, pyridine, dicyclohexylcarbodiimide / benzene / 6 h / 5 °C

5: 67 percent / boron trifluoride etherate / various solvent(s) / 3 h / -78 °C

With pyridine; boron trifluoride diethyl etherate; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1021/ja00197a047

Reference yield:

: 15922-23-3
1-(5-O-Acetyl-2,3-O-isopropylidene-β-D-ribofuranosyl)uracil

: 121845-99-6
1-(6,7,8-Trideoxy-2,3-O-isopropylidene-β-D-allo-oct-7-enofuranosyl)-3-(4-methoxybenzyl)uracil

Guidance literature:: Multi-step reaction with 4 steps

1: NaH / dimethylformamide / 0.17 h / 0 °C

2: K₂CO₃ / methanol / 2 h / Ambient temperature

3: 79 percent / dimethyl sulfoxide, trifluoroacetic acid, pyridine, dicyclohexylcarbodiimide / benzene / 6 h / 5 °C

4: 67 percent / boron trifluoride etherate / various solvent(s) / 3 h / -78 °C

With pyridine; boron trifluoride diethyl etherate; sodium hydride; potassium carbonate; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; In methanol; N,N-dimethyl-formamide; benzene;
DOI:10.1021/ja00197a047