methyl 1-<3,7-anhydro-2-O-benzoyl-5-O-benzyl-6-deoxy-β-L-glycero-D-allo-octofuranos-(1,4)-yl>uracil-5-carboxylate

Base Information

Chemical Name:methyl 1-<3,7-anhydro-2-O-benzoyl-5-O-benzyl-6-deoxy-β-L-glycero-D-allo-octofuranos-(1,4)-yl>uracil-5-carboxylate
CAS No.:111690-19-8
Molecular Formula:C₂₈H₂₈N₂O₁₀
Molecular Weight:552.538
Hs Code.:

Synonyms:methyl 1-<3,7-anhydro-2-O-benzoyl-5-O-benzyl-6-deoxy-β-L-glycero-D-allo-octofuranos-(1,4)-yl>uracil-5-carboxylate

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Chemical Property of methyl 1-<3,7-anhydro-2-O-benzoyl-5-O-benzyl-6-deoxy-β-L-glycero-D-allo-octofuranos-(1,4)-yl>uracil-5-carboxylate

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Technology Process of methyl 1-<3,7-anhydro-2-O-benzoyl-5-O-benzyl-6-deoxy-β-L-glycero-D-allo-octofuranos-(1,4)-yl>uracil-5-carboxylate

There total 10 articles about methyl 1-<3,7-anhydro-2-O-benzoyl-5-O-benzyl-6-deoxy-β-L-glycero-D-allo-octofuranos-(1,4)-yl>uracil-5-carboxylate 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: 77.0%

: 111690-18-7
methyl 1-<8-O-allyl-3,7-anhydro-2-O-benzoyl-5-O-benzyl-6-deoxy-β-L-glycero-D-allo-octofuranos-(1,4)-yl>uracil-5-carboxylate

: 111690-19-8
methyl 1-<3,7-anhydro-2-O-benzoyl-5-O-benzyl-6-deoxy-β-L-glycero-D-allo-octofuranos-(1,4)-yl>uracil-5-carboxylate

Guidance literature:: With selenium(IV) oxide; acetic acid; In 1,4-dioxane; for 0.75h; Heating;
DOI:10.1021/jo00237a011

Reference yield:

: 98-88-4
benzoyl chloride

: 111690-19-8
methyl 1-<3,7-anhydro-2-O-benzoyl-5-O-benzyl-6-deoxy-β-L-glycero-D-allo-octofuranos-(1,4)-yl>uracil-5-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 86 percent / pyridine / 1 h

2: 77 percent / SeO₂, HOAc / dioxane / 0.75 h / Heating

With pyridine; selenium(IV) oxide; acetic acid; In 1,4-dioxane;
DOI:10.1021/jo00237a011

Reference yield:

: 42821-92-1
methyl 2,4-dihydroxypyrimidine-5-carboxylate

: 111690-19-8
methyl 1-<3,7-anhydro-2-O-benzoyl-5-O-benzyl-6-deoxy-β-L-glycero-D-allo-octofuranos-(1,4)-yl>uracil-5-carboxylate

Guidance literature:: Multi-step reaction with 9 steps

1: 1.25 h / Heating

2: Me₃SiOSO₂CF₃ / CH₂Cl₂ / 2 h / Ambient temperature

3: sodium methoxide / methanol / 1 h / Ambient temperature

4: p-toluenesulfonic acid / dimethylformamide / 12 h / Ambient temperature

5: pyridine / 0.5 h

6: 90percent aq. trifluoroacetic acid / 0.5 h / Ambient temperature

7: 1.) NaH 2.) HCl / 1.) DMSO, 50 deg C, 2.5 h, 2.) MeOH, reflux, 0.5 h

8: 86 percent / pyridine / 1 h

9: 77 percent / SeO₂, HOAc / dioxane / 0.75 h / Heating

With pyridine; hydrogenchloride; selenium(IV) oxide; trimethylsilyl trifluoromethanesulfonate; sodium methylate; sodium hydride; toluene-4-sulfonic acid; acetic acid; trifluoroacetic acid; In 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00237a011