Carbonic acid benzyl ester (2R,3S,5R)-5-(4-benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-2-benzyloxycarbonyloxymethyl-tetrahydro-furan-3-yl ester

Base Information

• Chemical Name: Carbonic acid benzyl ester (2R,3S,5R)-5-(4-benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-2-benzyloxycarbonyloxymethyl-tetrahydro-furan-3-yl ester
• CAS No.: 82892-74-8
• Molecular Formula: C₃₃H₃₁N₃O₁₀
• Molecular Weight: 629.623

Synonyms:

Chemical Property of Carbonic acid benzyl ester (2R,3S,5R)-5-(4-benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-2-benzyloxycarbonyloxymethyl-tetrahydro-furan-3-yl ester

Chemical Property:

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Technology Process of Carbonic acid benzyl ester (2R,3S,5R)-5-(4-benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-2-benzyloxycarbonyloxymethyl-tetrahydro-furan-3-yl ester

There total 3 articles about Carbonic acid benzyl ester (2R,3S,5R)-5-(4-benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-2-benzyloxycarbonyloxymethyl-tetrahydro-furan-3-yl ester 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:

N-benzyloxycarbonylimidazole (22129-07-3) → Carbonic acid benzyl ester (2R,3S,5R)-5-(4-benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-2-benzyloxycarbonyloxymethyl-tetrahydro-furan-3-yl ester (82892-74-8)

Guidance literature:

Multi-step reaction with 2 steps

1: CH₂Cl₂ / 2 h

2: acetonitrile / 36 h / Ambient temperature

In dichloromethane; acetonitrile;

DOI:10.1021/ja00385a026

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → Carbonic acid benzyl ester (2R,3S,5R)-5-(4-benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-2-benzyloxycarbonyloxymethyl-tetrahydro-furan-3-yl ester (82892-74-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 78 percent / toluene / Ambient temperature

2: CH₂Cl₂ / 2 h

3: acetonitrile / 36 h / Ambient temperature

In dichloromethane; toluene; acetonitrile;

DOI:10.1021/ja00385a026

Reference yield:

1-(benzyloxycarbonyl)-3-ethylimidazolium tetrafluoroborate (82892-54-4) + 2'-Deoxycytidine (951-77-9) → 4-N-(benzyloxycarbonyl)-2'-deoxycytidine (82892-56-6) + 5'-O,4-N-bis(benzyloxycarbonyl)-2'-deoxycytidine (82892-55-5) + Carbonic acid benzyl ester (2R,3S,5R)-5-(4-benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-2-benzyloxycarbonyloxymethyl-tetrahydro-furan-3-yl ester (82892-74-8)

Guidance literature:

In acetonitrile; for 36h; Ambient temperature;

DOI:10.1021/ja00385a026

upstream raw materials:

1-(benzyloxycarbonyl)-3-ethylimidazolium tetrafluoroborate

2'-Deoxycytidine

N-benzyloxycarbonylimidazole

benzyl chloroformate

Downstream raw materials:

C₅₃H₅₁ClN₅O₁₄P

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