2-Oxa-6-azabicyclo[3.2.0]heptane, 1-(3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)-6-(phenoxyacetyl)-4-(phenyl methoxy)-3-[(phenylmethoxy)methyl]-, (1R,3R,4S,5R)-

Base Information

• Chemical Name: 2-Oxa-6-azabicyclo[3.2.0]heptane, 1-(3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)-6-(phenoxyacetyl)-4-(phenyl methoxy)-3-[(phenylmethoxy)methyl]-, (1R,3R,4S,5R)-
• CAS No.: 874812-56-3
• Molecular Formula: C32H31N3O7
• Molecular Weight: 569.614

Synonyms:

Chemical Property of 2-Oxa-6-azabicyclo[3.2.0]heptane, 1-(3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)-6-(phenoxyacetyl)-4-(phenyl methoxy)-3-[(phenylmethoxy)methyl]-, (1R,3R,4S,5R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Oxa-6-azabicyclo[3.2.0]heptane, 1-(3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)-6-(phenoxyacetyl)-4-(phenyl methoxy)-3-[(phenylmethoxy)methyl]-, (1R,3R,4S,5R)-

There total 12 articles about 2-Oxa-6-azabicyclo[3.2.0]heptane, 1-(3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)-6-(phenoxyacetyl)-4-(phenyl methoxy)-3-[(phenylmethoxy)methyl]-, (1R,3R,4S,5R)- 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: 84.0%

(1R,3R,4S,5R)-3-benzyloxymethyl-4-benzyloxy-1-(uracil-1-yl)-6-aza-2-oxabicyclo[3.2.0]heptane (874812-55-2) + Phenoxyacetyl chloride (701-99-5) → (1R,3R,4S,5R)-3-benzyloxymethyl-4-benzyloxy-6-N-(phenoxyacetyl)-1-(uracil-1-yl)-6-aza-2-oxabicyclo[3.2.0]heptane (874812-56-3)

Guidance literature:

With pyridine; at 20 ℃; for 2.5h;

DOI:10.1021/jo052115x

Reference yield:

1-((2R,3R,4S,5R)-5-Benzyloxymethyl-3,4-dihydroxy-2-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione → (1R,3R,4S,5R)-3-benzyloxymethyl-4-benzyloxy-6-N-(phenoxyacetyl)-1-(uracil-1-yl)-6-aza-2-oxabicyclo[3.2.0]heptane (874812-56-3)

Guidance literature:

Multi-step reaction with 11 steps

1: 3.1 g / pyridine / 24 h / 20 °C

2: 91 percent / diphenyl carbonate; NaHCO₃ / dimethylformamide / 2 h / 110 °C

3: 85 percent / NaH / acetonitrile / 0 - 20 °C

4: 79 percent / aq. AcOH / 48 h / 20 °C

5: 89 percent / pyridine / 1.5 h / 0 °C

6: 87 percent / NaN₃ / dimethylformamide / 60 h / 100 °C

7: 85 percent / aq. NaOH / ethanol; tetrahydrofuran / 2 h / 20 °C

8: 90 percent / pyridine / 24 h / 0 °C

9: 90 percent / PMe₃; H₂O / tetrahydrofuran / 1 h / 20 °C

10: 63 percent / pyridine; Et₃N / 48 h / 90 °C

11: 84 percent / pyridine / 2.5 h / 20 °C

With pyridine; bis(phenyl) carbonate; sodium hydroxide; sodium azide; water; sodium hydride; sodium hydrogencarbonate; acetic acid; triethylamine; trimethylphosphane; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo052115x

Reference yield:

(2R,3R,3aS,9aR)-3-Benzyloxy-2-benzyloxymethyl-9a-hydroxymethyl-2,3,3a,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one (874812-49-4) → (1R,3R,4S,5R)-3-benzyloxymethyl-4-benzyloxy-6-N-(phenoxyacetyl)-1-(uracil-1-yl)-6-aza-2-oxabicyclo[3.2.0]heptane (874812-56-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 89 percent / pyridine / 1.5 h / 0 °C

2: 87 percent / NaN₃ / dimethylformamide / 60 h / 100 °C

3: 85 percent / aq. NaOH / ethanol; tetrahydrofuran / 2 h / 20 °C

4: 90 percent / pyridine / 24 h / 0 °C

5: 90 percent / PMe₃; H₂O / tetrahydrofuran / 1 h / 20 °C

6: 63 percent / pyridine; Et₃N / 48 h / 90 °C

7: 84 percent / pyridine / 2.5 h / 20 °C

With pyridine; sodium hydroxide; sodium azide; water; triethylamine; trimethylphosphane; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jo052115x

upstream raw materials:

(1R,3R,4S,5R)-3-benzyloxymethyl-4-benzyloxy-1-(uracil-1-yl)-6-aza-2-oxabicyclo[3.2.0]heptane

Phenoxyacetyl chloride

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

2,3'-anhydro-1-[1-azido-4,6-di-O-benzyl-1-deoxy-β-D-fructofuranosyl]uracil

Downstream raw materials:

1-[(1R,3R,4S,5R)-4-Hydroxy-3-hydroxymethyl-6-(2-phenoxy-acetyl)-2-oxa-6-aza-bicyclo[3.2.0]hept-1-yl]-1H-pyrimidine-2,4-dione

(1R,3R,4S,5R)-3-(4,4'-dimethoxytrityloxymethyl)-4-hydroxy-6-N-(phenoxyacetyl)-1-(uracil-1-yl)-6-aza-2-oxabicyclo[3.2.0]heptane

(1R,3R,4S,5R)-1-(cytosin-1-yl)-3-(4,4'-dimethoxytrityloxymethyl)-4-hydroxy-6-N-(phenoxyacetyl)-6-aza-2-oxabicyclo[3.2.0]heptane

(1R,3R,4S,5R)-3-(4,4'-dimethoxytrityloxymethyl)-4-hydroxy-1-(4-N-isobutyrylcytosin-1-yl)-6-N-phenoxyacetyl-6-aza-2-oxabicyclo[3.2.0]heptane

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