1-((2R,3S,3aR,7S,7aS)-3a,7-bis(benzyloxy)hexahydro-2H-3,7a-(epoxymethano)benzofuran-2-yl)-5-ethylpyrimidine-2,4(1H,3H)-dione

Base Information

• Chemical Name: 1-((2R,3S,3aR,7S,7aS)-3a,7-bis(benzyloxy)hexahydro-2H-3,7a-(epoxymethano)benzofuran-2-yl)-5-ethylpyrimidine-2,4(1H,3H)-dione
• CAS No.: 1453218-14-8
• Molecular Formula: C₂₈H₃₀N₂O₆
• Molecular Weight: 490.556

Synonyms:1-((2R,3S,3aR,7S,7aS)-3a,7-bis(benzyloxy)hexahydro-2H-3,7a-(epoxymethano)benzofuran-2-yl)-5-ethylpyrimidine-2,4(1H,3H)-dione

Chemical Property of 1-((2R,3S,3aR,7S,7aS)-3a,7-bis(benzyloxy)hexahydro-2H-3,7a-(epoxymethano)benzofuran-2-yl)-5-ethylpyrimidine-2,4(1H,3H)-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-((2R,3S,3aR,7S,7aS)-3a,7-bis(benzyloxy)hexahydro-2H-3,7a-(epoxymethano)benzofuran-2-yl)-5-ethylpyrimidine-2,4(1H,3H)-dione

There total 28 articles about 1-((2R,3S,3aR,7S,7aS)-3a,7-bis(benzyloxy)hexahydro-2H-3,7a-(epoxymethano)benzofuran-2-yl)-5-ethylpyrimidine-2,4(1H,3H)-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: 96.0%

((5aR,6aS,7S,10aR,10bS)-7,10a-bis(benzyloxy)-3-methyl-2-oxo-7,8,9,10,10a,10b-hexahydro-2H-benzofuro[2′,3′:4,5]oxazolo[3,2-a]pyrimidin-6a(5aH)-yl)methyl methanesulfonate (1453218-11-5) → 1-((2R,3S,3aR,7S,7aS)-3a,7-bis(benzyloxy)hexahydro-2H-3,7a-(epoxymethano)benzofuran-2-yl)-5-ethylpyrimidine-2,4(1H,3H)-dione (1453218-14-8)

Guidance literature:

With water; sodium hydroxide; In ethanol; at 100 ℃; for 0.5h;

DOI:10.1021/jo401170y

Reference yield:

1,2-O-isopropylidene-3-keto-4-C-(tert-butyldiphenylsilyl)oxymethyl-5-O-(tert-butyldimethylsilyl)-6-deoxy-6-C-vinyl-β-Lmannofuranose (1453217-91-8) → 1-((2R,3S,3aR,7S,7aS)-3a,7-bis(benzyloxy)hexahydro-2H-3,7a-(epoxymethano)benzofuran-2-yl)-5-ethylpyrimidine-2,4(1H,3H)-dione (1453218-14-8)

Guidance literature:

Multi-step reaction with 18 steps

1.1: oxygen; copper diacetate; palladium dichloride / water; N,N-dimethyl acetamide / 24 h / 40 °C

2.1: L-proline / dimethyl sulfoxide / 54 h / 55 °C / Inert atmosphere

3.1: acetic acid; tetramethylammonium triacetoxyborohydride / acetonitrile / 7 h / 0 - 23 °C / Inert atmosphere

4.1: dmap / dichloromethane / 19 h / 40 °C / Inert atmosphere

5.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 0.25 h / 110 °C

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

7.1: sodium hydride; tetra-(n-butyl)ammonium iodide / mineral oil; N,N-dimethyl-formamide; tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 24 h / 23 °C / Inert atmosphere

9.1: sodium hydride; tetra-(n-butyl)ammonium iodide / mineral oil; N,N-dimethyl-formamide; tetrahydrofuran / 3 h / 0 - 23 °C / Inert atmosphere

10.1: iron(III) chloride hexahydrate / dichloromethane / 1 h / 0 - 23 °C

11.1: pyridine; dmap / dichloromethane / 1 h / 0 - 23 °C / Inert atmosphere

12.1: N,O-bis-(trimethylsilyl)-acetamide / 1,2-dichloro-ethane / 1 h / 90 °C / Inert atmosphere

12.2: 13 h / 0 - 55 °C / Inert atmosphere

13.1: potassium carbonate / methanol / 18 h / 23 °C / Inert atmosphere

14.1: pyridine; dmap / 16 h / 0 - 23 °C / Inert atmosphere

15.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 75 h / 80 °C / Inert atmosphere

16.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 3 h / 23 °C

17.1: pyridine; dmap / 12 h / 0 - 23 °C / Inert atmosphere

18.1: water; sodium hydroxide / ethanol / 0.5 h / 100 °C

With pyridine; dmap; N,O-bis-(trimethylsilyl)-acetamide; 2,2'-azobis(isobutyronitrile); iron(III) chloride hexahydrate; tetrabutyl ammonium fluoride; water; oxygen; tri-n-butyl-tin hydride; copper diacetate; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 2,3-dicyano-5,6-dichloro-p-benzoquinone; L-proline; sodium hydroxide; palladium dichloride; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl acetamide; water; dimethyl sulfoxide; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil; 2.1: |Aldol Condensation / 5.1: |Barton-McCombie Deoxygenation / 12.1: |Vorbrueggen Nucleoside Synthesis / 12.2: |Vorbrueggen Nucleoside Synthesis;

DOI:10.1021/jo401170y

Reference yield:

((3aR,5R,6S,6aR)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-6-(naphthalen-2-ylmethoxy)tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol (956485-08-8) → 1-((2R,3S,3aR,7S,7aS)-3a,7-bis(benzyloxy)hexahydro-2H-3,7a-(epoxymethano)benzofuran-2-yl)-5-ethylpyrimidine-2,4(1H,3H)-dione (1453218-14-8)

Guidance literature:

Multi-step reaction with 23 steps

1.1: pyridinium chlorochromate / dichloromethane / 13 h / 40 °C / Inert atmosphere

2.1: boron trifluoride diethyl etherate / dichloromethane / 0.08 h / -41 °C / Inert atmosphere

2.2: 2 h / -41 °C / Inert atmosphere

3.1: pyridine / dichloromethane / 3 h / 0 - 23 °C / Inert atmosphere

4.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 6 h / 23 °C

5.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 18 h / 23 °C / Inert atmosphere

6.1: oxygen; copper diacetate; palladium dichloride / water; N,N-dimethyl acetamide / 24 h / 40 °C

7.1: L-proline / dimethyl sulfoxide / 54 h / 55 °C / Inert atmosphere

8.1: acetic acid; tetramethylammonium triacetoxyborohydride / acetonitrile / 7 h / 0 - 23 °C / Inert atmosphere

9.1: dmap / dichloromethane / 19 h / 40 °C / Inert atmosphere

10.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 0.25 h / 110 °C

11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

12.1: sodium hydride; tetra-(n-butyl)ammonium iodide / mineral oil; N,N-dimethyl-formamide; tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

13.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 24 h / 23 °C / Inert atmosphere

14.1: sodium hydride; tetra-(n-butyl)ammonium iodide / mineral oil; N,N-dimethyl-formamide; tetrahydrofuran / 3 h / 0 - 23 °C / Inert atmosphere

15.1: iron(III) chloride hexahydrate / dichloromethane / 1 h / 0 - 23 °C

16.1: pyridine; dmap / dichloromethane / 1 h / 0 - 23 °C / Inert atmosphere

17.1: N,O-bis-(trimethylsilyl)-acetamide / 1,2-dichloro-ethane / 1 h / 90 °C / Inert atmosphere

17.2: 13 h / 0 - 55 °C / Inert atmosphere

18.1: potassium carbonate / methanol / 18 h / 23 °C / Inert atmosphere

19.1: pyridine; dmap / 16 h / 0 - 23 °C / Inert atmosphere

20.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 75 h / 80 °C / Inert atmosphere

21.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 3 h / 23 °C

22.1: pyridine; dmap / 12 h / 0 - 23 °C / Inert atmosphere

23.1: water; sodium hydroxide / ethanol / 0.5 h / 100 °C

With pyridine; dmap; N,O-bis-(trimethylsilyl)-acetamide; 2,2'-azobis(isobutyronitrile); iron(III) chloride hexahydrate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; oxygen; tri-n-butyl-tin hydride; copper diacetate; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; L-proline; sodium hydroxide; palladium dichloride; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl acetamide; water; dimethyl sulfoxide; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil; 2.1: |Sakurai Allylation / 5.1: |Wacker Oxidation / 7.1: |Aldol Condensation / 10.1: |Barton-McCombie Deoxygenation / 17.1: |Vorbrueggen Nucleoside Synthesis / 17.2: |Vorbrueggen Nucleoside Synthesis;

DOI:10.1021/jo401170y

upstream raw materials:

((3aR,5R,6S,6aR)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-6-(naphthalen-2-ylmethoxy)tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol

1,2-O-isopropylidene-3-O-(2-naphthylmethyl)-4-C-(tert-butyldiphenylsilyl)oxymethyl-5-O-(tert-butyldimethylsilyl)-6-deoxy-6-C-vinyl-β-L-mannofuranose

C₃₄H₅₂O₆Si₂

1,2-O-isopropylidene-3-keto-4-C-(tert-butyldiphenylsilyl)oxymethyl-5-O-(tert-butyldimethylsilyl)-6-deoxy-6-C-vinyl-β-Lmannofuranose

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