1-((3aS,4R,4aR,6R,7R,7aS,7bS)-4,7a-Bis-benzyloxy-7-hydroxy-2,2-dimethyl-hexahydro-furo[3',2':3,4]cyclopenta[1,2-d][1,3]dioxol-6-yl)-5-methyl-1H-pyrimidine-2,4-dione

Base Information

Chemical Name:1-((3aS,4R,4aR,6R,7R,7aS,7bS)-4,7a-Bis-benzyloxy-7-hydroxy-2,2-dimethyl-hexahydro-furo[3',2':3,4]cyclopenta[1,2-d][1,3]dioxol-6-yl)-5-methyl-1H-pyrimidine-2,4-dione
CAS No.:557099-60-2
Molecular Formula:C₂₉H₃₂N₂O₈
Molecular Weight:536.582
Hs Code.:

1-((3aS,4R,4aR,6R,7R,7aS,7bS)-4,7a-Bis-benzyloxy-7-hydroxy-2,2-dimethyl-hexahydro-furo[3',2':3,4]cyclopenta[1,2-d][1,3]dioxol-6-yl)-5-methyl-1H-pyrimidine-2,4-dione

Synonyms:1-((3aS,4R,4aR,6R,7R,7aS,7bS)-4,7a-Bis-benzyloxy-7-hydroxy-2,2-dimethyl-hexahydro-furo[3',2':3,4]cyclopenta[1,2-d][1,3]dioxol-6-yl)-5-methyl-1H-pyrimidine-2,4-dione

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Chemical Property of 1-((3aS,4R,4aR,6R,7R,7aS,7bS)-4,7a-Bis-benzyloxy-7-hydroxy-2,2-dimethyl-hexahydro-furo[3',2':3,4]cyclopenta[1,2-d][1,3]dioxol-6-yl)-5-methyl-1H-pyrimidine-2,4-dione

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Technology Process of 1-((3aS,4R,4aR,6R,7R,7aS,7bS)-4,7a-Bis-benzyloxy-7-hydroxy-2,2-dimethyl-hexahydro-furo[3',2':3,4]cyclopenta[1,2-d][1,3]dioxol-6-yl)-5-methyl-1H-pyrimidine-2,4-dione

There total 6 articles about 1-((3aS,4R,4aR,6R,7R,7aS,7bS)-4,7a-Bis-benzyloxy-7-hydroxy-2,2-dimethyl-hexahydro-furo[3',2':3,4]cyclopenta[1,2-d][1,3]dioxol-6-yl)-5-methyl-1H-pyrimidine-2,4-dione 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: 66.0%

: 77-76-9
2,2-dimethoxy-propane

: 557099-59-9
(1R,3R,4R,5R,6S,7S,8R)-5,8-dibenzyloxy-4,6,7-trihydroxy-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]octane

: 557099-60-2
1-((3aS,4R,4aR,6R,7R,7aS,7bS)-4,7a-Bis-benzyloxy-7-hydroxy-2,2-dimethyl-hexahydro-furo[3',2':3,4]cyclopenta[1,2-d][1,3]dioxol-6-yl)-5-methyl-1H-pyrimidine-2,4-dione

Guidance literature:: With toluene-4-sulfonic acid; In acetone; at 20 ℃; for 16h;
DOI:10.1039/b210439c

Reference yield:

: 557099-55-5
(1R,3R,7R,8R,9S,10S,11R)-8,11-dibenzyloxy-9,10-dihydroxy-5,5-dimethyl-2,4,6-trioxatricyclo[6.3.0.0^3,7]undecane

: 557099-60-2
1-((3aS,4R,4aR,6R,7R,7aS,7bS)-4,7a-Bis-benzyloxy-7-hydroxy-2,2-dimethyl-hexahydro-furo[3',2':3,4]cyclopenta[1,2-d][1,3]dioxol-6-yl)-5-methyl-1H-pyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 6 steps

1: 76 percent / pyridine / 16 h / 20 °C

2: aq. AcOH / 16 h / 90 °C

3: 200 mg / pyridine / 16 h

4: 65 percent / N,O-bis(trimethylsilyl)acetamide; trimethylsilyl triflate / acetonitrile / 16 h / 50 °C

5: 95 percent / NaOMe / methanol / 16 h / 20 °C

6: 66 percent / p-TsOH*H₂O / acetone / 16 h / 20 °C

With pyridine; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; sodium methylate; toluene-4-sulfonic acid; acetic acid; In methanol; acetone; acetonitrile;
DOI:10.1039/b210439c

Reference yield:

: Acetic acid (3R,3aS,4S,5S,6R,6aR)-5-acetoxy-3a,6-bis-benzyloxy-2,3-dihydroxy-hexahydro-cyclopenta[b]furan-4-yl ester

: 557099-60-2
1-((3aS,4R,4aR,6R,7R,7aS,7bS)-4,7a-Bis-benzyloxy-7-hydroxy-2,2-dimethyl-hexahydro-furo[3',2':3,4]cyclopenta[1,2-d][1,3]dioxol-6-yl)-5-methyl-1H-pyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 4 steps

1: 200 mg / pyridine / 16 h

2: 65 percent / N,O-bis(trimethylsilyl)acetamide; trimethylsilyl triflate / acetonitrile / 16 h / 50 °C

3: 95 percent / NaOMe / methanol / 16 h / 20 °C

4: 66 percent / p-TsOH*H₂O / acetone / 16 h / 20 °C

With pyridine; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; sodium methylate; toluene-4-sulfonic acid; In methanol; acetone; acetonitrile;
DOI:10.1039/b210439c