{3-Benzyloxycarbonylamino-5-[cyclopropyl-(4-hydroxy-2-oxo-5,6,7,8,9,10-hexahydro-2H-cycloocta[b]pyran-3-yl)-methyl]-phenyl}-carbamic acid benzyl ester

Base Information

• Chemical Name: {3-Benzyloxycarbonylamino-5-[cyclopropyl-(4-hydroxy-2-oxo-5,6,7,8,9,10-hexahydro-2H-cycloocta[b]pyran-3-yl)-methyl]-phenyl}-carbamic acid benzyl ester
• CAS No.: 188308-36-3
• Molecular Formula: C₃₇H₃₈N₂O₇
• Molecular Weight: 622.718

Synonyms:{3-Benzyloxycarbonylamino-5-[cyclopropyl-(4-hydroxy-2-oxo-5,6,7,8,9,10-hexahydro-2H-cycloocta[b]pyran-3-yl)-methyl]-phenyl}-carbamic acid benzyl ester

Chemical Property of {3-Benzyloxycarbonylamino-5-[cyclopropyl-(4-hydroxy-2-oxo-5,6,7,8,9,10-hexahydro-2H-cycloocta[b]pyran-3-yl)-methyl]-phenyl}-carbamic acid benzyl ester

Chemical Property:

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Technology Process of {3-Benzyloxycarbonylamino-5-[cyclopropyl-(4-hydroxy-2-oxo-5,6,7,8,9,10-hexahydro-2H-cycloocta[b]pyran-3-yl)-methyl]-phenyl}-carbamic acid benzyl ester

There total 6 articles about {3-Benzyloxycarbonylamino-5-[cyclopropyl-(4-hydroxy-2-oxo-5,6,7,8,9,10-hexahydro-2H-cycloocta[b]pyran-3-yl)-methyl]-phenyl}-carbamic acid benzyl 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: 76.0%

5,6,7,8,9,10-Hexahydro-4-hydroxy-2H-cyclooctapyran-2-on (100058-82-0) + [3-Benzyloxycarbonylamino-5-(cyclopropyl-hydroxy-methyl)-phenyl]-carbamic acid benzyl ester (188308-35-2) → {3-Benzyloxycarbonylamino-5-[cyclopropyl-(4-hydroxy-2-oxo-5,6,7,8,9,10-hexahydro-2H-cycloocta[b]pyran-3-yl)-methyl]-phenyl}-carbamic acid benzyl ester (188308-36-3)

Guidance literature:

With molecular sieve; toluene-4-sulfonic acid; In dichloromethane; a) RT, 1.5 h, b) reflux, 1.5 h;

DOI:10.1021/jm960441m

Reference yield:

3.5-diaminobenzoic acid (535-87-5) → {3-Benzyloxycarbonylamino-5-[cyclopropyl-(4-hydroxy-2-oxo-5,6,7,8,9,10-hexahydro-2H-cycloocta[b]pyran-3-yl)-methyl]-phenyl}-carbamic acid benzyl ester (188308-36-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 43 percent / (dimethylamino)pyridine, pyridine / 0 - 20 °C

2: 65 percent / BH₃*THF / tetrahydrofuran / 5.5 h / -10 °C

3: 1.) DMSO, oxalyl chloride, 2.) diisopropylethylamine / 1.) CH₂Cl₂, -30 deg C, 1 h, 2.) CH₂Cl₂, from -25 deg C to RT, 1 h

4: 1.) t-BuLi / 1.) THF, -78 deg C, 15 min, 2.) THF, from -78 deg C to RT, 1.5 h

5: 76 percent / p-toluenesulfonic acid, molecular sieves / CH₂Cl₂ / a) RT, 1.5 h, b) reflux, 1.5 h

With pyridine; dmap; molecular sieve; borane-THF; oxalyl dichloride; tert.-butyl lithium; toluene-4-sulfonic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm960441m

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → {3-Benzyloxycarbonylamino-5-[cyclopropyl-(4-hydroxy-2-oxo-5,6,7,8,9,10-hexahydro-2H-cycloocta[b]pyran-3-yl)-methyl]-phenyl}-carbamic acid benzyl ester (188308-36-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 43 percent / (dimethylamino)pyridine, pyridine / 0 - 20 °C

2: 65 percent / BH₃*THF / tetrahydrofuran / 5.5 h / -10 °C

3: 1.) DMSO, oxalyl chloride, 2.) diisopropylethylamine / 1.) CH₂Cl₂, -30 deg C, 1 h, 2.) CH₂Cl₂, from -25 deg C to RT, 1 h

4: 1.) t-BuLi / 1.) THF, -78 deg C, 15 min, 2.) THF, from -78 deg C to RT, 1.5 h

5: 76 percent / p-toluenesulfonic acid, molecular sieves / CH₂Cl₂ / a) RT, 1.5 h, b) reflux, 1.5 h

With pyridine; dmap; molecular sieve; borane-THF; oxalyl dichloride; tert.-butyl lithium; toluene-4-sulfonic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm960441m

upstream raw materials:

5,6,7,8,9,10-Hexahydro-4-hydroxy-2H-cyclooctapyran-2-on

[3-Benzyloxycarbonylamino-5-(cyclopropyl-hydroxy-methyl)-phenyl]-carbamic acid benzyl ester

3.5-diaminobenzoic acid

benzyl chloroformate

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