(2R,3S,3aS,9aR)-3-Benzyloxy-2-benzyloxymethyl-2,3,3a,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one

Base Information

• Chemical Name: (2R,3S,3aS,9aR)-3-Benzyloxy-2-benzyloxymethyl-2,3,3a,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one
• CAS No.: 309250-55-3
• Molecular Formula: C₂₃H₂₂N₂O₅
• Molecular Weight: 406.438

Synonyms:(2R,3S,3aS,9aR)-3-Benzyloxy-2-benzyloxymethyl-2,3,3a,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one

Chemical Property of (2R,3S,3aS,9aR)-3-Benzyloxy-2-benzyloxymethyl-2,3,3a,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one

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Technology Process of (2R,3S,3aS,9aR)-3-Benzyloxy-2-benzyloxymethyl-2,3,3a,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one

There total 2 articles about (2R,3S,3aS,9aR)-3-Benzyloxy-2-benzyloxymethyl-2,3,3a,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one 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: 78.0%

1-(3',5'-di-O-benzyl-2'-deoxy-2'-iodo-β-D-xylofuranosyl)uracil (309250-53-1) → (2R,3S,3aS,9aR)-3-Benzyloxy-2-benzyloxymethyl-2,3,3a,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one (309250-55-3)

Guidance literature:

With di(n-butyl)tin oxide; In N,N-dimethyl-formamide; at 120 ℃; for 3h;

DOI:10.1016/S0957-4166(00)00272-X

Reference yield:

1,4-anhydro-3,5-di-O-benzyl-2-deoxy-D-threo-pent-1-enitol (110237-88-2) → (2R,3S,3aS,9aR)-3-Benzyloxy-2-benzyloxymethyl-2,3,3a,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one (309250-55-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / NIS / CH₂Cl₂ / 2 h / 20 °C

2: 78 percent / n-dibutyltin oxide / dimethylformamide / 3 h / 120 °C

With N-iodo-succinimide; di(n-butyl)tin oxide; In dichloromethane; N,N-dimethyl-formamide; 1: Iodination / 2: Dehydroiodination;

DOI:10.1016/S0957-4166(00)00272-X

Reference yield: 55.0%

(2R,3S,3aS,9aR)-3-Benzyloxy-2-benzyloxymethyl-2,3,3a,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one (309250-55-3) → 1-((2R,3R,4R,5R)-3-Azido-4-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 120 ℃; for 48h;

DOI:10.1016/S0957-4166(00)00272-X

upstream raw materials:

1-(3',5'-di-O-benzyl-2'-deoxy-2'-iodo-β-D-xylofuranosyl)uracil

1,4-anhydro-3,5-di-O-benzyl-2-deoxy-D-threo-pent-1-enitol

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