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

Base Information

• Chemical Name: 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
• CAS No.: 111690-18-7
• Molecular Formula: C₃₁H₃₂N₂O₁₀
• Molecular Weight: 592.602
• Mol file: 111690-18-7.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 8 articles about 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 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: 86.0%

benzoyl chloride (98-88-4) + methyl 1-<8-O-allyl-3,7-anhydro-5-O-benzyl-6-deoxy-β-L-glycero-D-allo-octofuranos-(1,4)-yl>uracil-5-carboxylate (111690-17-6) → 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 (111690-18-7)

Guidance literature:

With pyridine; for 1h;

DOI:10.1021/jo00237a011

Reference yield:

methyl 2,4-dihydroxypyrimidine-5-carboxylate (42821-92-1) → 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 (111690-18-7)

Guidance literature:

Multi-step reaction with 8 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

With pyridine; hydrogenchloride; trimethylsilyl trifluoromethanesulfonate; sodium methylate; sodium hydride; toluene-4-sulfonic acid; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00237a011

Reference yield:

1-[(2R,3R,4S,5S)-5-((1R,3S)-4-Allyloxy-1-benzyloxy-3-hydroxy-butyl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid methyl ester → 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 (111690-18-7)

Guidance literature:

Multi-step reaction with 5 steps

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

2: pyridine / 0.5 h

3: 90percent aq. trifluoroacetic acid / 0.5 h / Ambient temperature

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

5: 86 percent / pyridine / 1 h

With pyridine; hydrogenchloride; sodium hydride; toluene-4-sulfonic acid; trifluoroacetic acid; In N,N-dimethyl-formamide;

DOI:10.1021/jo00237a011

upstream raw materials:

benzoyl chloride

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

methyl 2,4-dihydroxypyrimidine-5-carboxylate

methyl 1-<8-O-allyl-5-O-benzyl-6-deoxy-7-O-(methylsulfonyl)-β-D-glycero-D-allo-octofuranos-(1,4)-yl>uracil-5-carboxylate

Downstream raw materials:

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

1-((2R,3R,3aS,7R,7aR)-5-Carboxy-3,7-dihydroxy-hexahydro-furo[3,2-b]pyran-2-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid

methyl 1-uracil-5-carboxylate