1-Phenyl-3-((1R,2R,6R,7S,11S)-4,4,11-trimethyl-9-oxo-3,5,8,10-tetraoxa-tricyclo[5.2.2.0^2,6]undec-1-yl)-urea

Base Information

• Chemical Name: 1-Phenyl-3-((1R,2R,6R,7S,11S)-4,4,11-trimethyl-9-oxo-3,5,8,10-tetraoxa-tricyclo[5.2.2.0^2,6]undec-1-yl)-urea
• CAS No.: 175848-47-2
• Molecular Formula: C₁₇H₂₀N₂O₆
• Molecular Weight: 348.356

Synonyms:1-Phenyl-3-((1R,2R,6R,7S,11S)-4,4,11-trimethyl-9-oxo-3,5,8,10-tetraoxa-tricyclo[5.2.2.0^2,6]undec-1-yl)-urea

Chemical Property of 1-Phenyl-3-((1R,2R,6R,7S,11S)-4,4,11-trimethyl-9-oxo-3,5,8,10-tetraoxa-tricyclo[5.2.2.0^2,6]undec-1-yl)-urea

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Technology Process of 1-Phenyl-3-((1R,2R,6R,7S,11S)-4,4,11-trimethyl-9-oxo-3,5,8,10-tetraoxa-tricyclo[5.2.2.0^2,6]undec-1-yl)-urea

There total 4 articles about 1-Phenyl-3-((1R,2R,6R,7S,11S)-4,4,11-trimethyl-9-oxo-3,5,8,10-tetraoxa-tricyclo[5.2.2.0^2,6]undec-1-yl)-urea 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: 85.0%

phenyl isocyanate (103-71-9) + (1R,2R,6R,7S,11S)-1-Amino-4,4,11-trimethyl-3,5,8,10-tetraoxa-tricyclo[5.2.2.02,6]undecan-9-one (175848-45-0) → 1-Phenyl-3-((1R,2R,6R,7S,11S)-4,4,11-trimethyl-9-oxo-3,5,8,10-tetraoxa-tricyclo[5.2.2.02,6]undec-1-yl)-urea (175848-47-2)

Guidance literature:

With pyridine; In tetrahydrofuran;

DOI:10.1016/0957-4166(96)00014-6

Reference yield:

(3aS,4S,7R,7aS)-7-Azido-4-((S)-1-hydroxy-ethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-one (175848-41-6) → 1-Phenyl-3-((1R,2R,6R,7S,11S)-4,4,11-trimethyl-9-oxo-3,5,8,10-tetraoxa-tricyclo[5.2.2.02,6]undec-1-yl)-urea (175848-47-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / H₂ / Pd black / ethanol

2: 79 percent / N-bromosuccinimide, AcONa / acetonitrile

3: 85 percent / pyridine / tetrahydrofuran

With pyridine; N-Bromosuccinimide; hydrogen; sodium acetate; palladium; In tetrahydrofuran; ethanol; acetonitrile;

DOI:10.1016/0957-4166(96)00014-6

Reference yield:

Trifluoro-methanesulfonic acid (3aS,4S,7R,7aR)-4-((S)-1-hydroxy-ethyl)-2,2-dimethyl-6-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester (175848-39-2) → 1-Phenyl-3-((1R,2R,6R,7S,11S)-4,4,11-trimethyl-9-oxo-3,5,8,10-tetraoxa-tricyclo[5.2.2.02,6]undec-1-yl)-urea (175848-47-2)

Guidance literature:

Multi-step reaction with 4 steps

1: NaN₃ / dimethylformamide

2: 90 percent / H₂ / Pd black / ethanol

3: 79 percent / N-bromosuccinimide, AcONa / acetonitrile

4: 85 percent / pyridine / tetrahydrofuran

With pyridine; N-Bromosuccinimide; sodium azide; hydrogen; sodium acetate; palladium; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/0957-4166(96)00014-6

upstream raw materials:

phenyl isocyanate

(1R,2R,6R,7S,11S)-1-Amino-4,4,11-trimethyl-3,5,8,10-tetraoxa-tricyclo[5.2.2.0^2,6]undecan-9-one

(3aS,4S,7R,7aS)-7-Amino-4-((S)-1-hydroxy-ethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-one

(3aS,4S,7R,7aS)-7-Azido-4-((S)-1-hydroxy-ethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-one

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