trans-4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)cyclohexyl (1R,2R,4S,6R,7R,9R)-4-ethenyl-2,4,7,14-tetramethyl-9-(methyloxy)-3-oxotricyclo[5.4.3.0(1,8)]tetradec-6-yl imidodicarbonate

Base Information

• Chemical Name: trans-4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)cyclohexyl (1R,2R,4S,6R,7R,9R)-4-ethenyl-2,4,7,14-tetramethyl-9-(methyloxy)-3-oxotricyclo[5.4.3.0(1,8)]tetradec-6-yl imidodicarbonate
• CAS No.: 937369-86-3
• Molecular Formula: C₃₄H₅₄N₂O₈
• Molecular Weight: 618.811

Synonyms:trans-4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)cyclohexyl (1R,2R,4S,6R,7R,9R)-4-ethenyl-2,4,7,14-tetramethyl-9-(methyloxy)-3-oxotricyclo[5.4.3.0(1,8)]tetradec-6-yl imidodicarbonate

Chemical Property of trans-4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)cyclohexyl (1R,2R,4S,6R,7R,9R)-4-ethenyl-2,4,7,14-tetramethyl-9-(methyloxy)-3-oxotricyclo[5.4.3.0(1,8)]tetradec-6-yl imidodicarbonate

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Technology Process of trans-4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)cyclohexyl (1R,2R,4S,6R,7R,9R)-4-ethenyl-2,4,7,14-tetramethyl-9-(methyloxy)-3-oxotricyclo[5.4.3.0(1,8)]tetradec-6-yl imidodicarbonate

There total 2 articles about trans-4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)cyclohexyl (1R,2R,4S,6R,7R,9R)-4-ethenyl-2,4,7,14-tetramethyl-9-(methyloxy)-3-oxotricyclo[5.4.3.0(1,8)]tetradec-6-yl imidodicarbonate 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: 90.0%

(3R,3aS,4R,5R,7S,9R,9aR,12R)-3-methoxy-4,7,9,12-tetramethyl-8-oxo-7-vinyldecahydro-4,9a-propanocyclopenta[8]annulen-5-yl carbamate (937369-83-0) + C15H23N3O4 (937369-84-1) → trans-4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)cyclohexyl (1R,2R,4S,6R,7R,9R)-4-ethenyl-2,4,7,14-tetramethyl-9-(methyloxy)-3-oxotricyclo[5.4.3.0(1,8)]tetradec-6-yl imidodicarbonate (937369-86-3)

Guidance literature:

(3R,3aS,4R,5R,7S,9R,9aR,12R)-3-methoxy-4,7,9,12-tetramethyl-8-oxo-7-vinyldecahydro-4,9a-propanocyclopenta[8]annulen-5-yl carbamate; C₁₅H₂₃N₃O₄; With sodium tert-pentoxide; In 1-methyl-pyrrolidin-2-one; at 5 ℃; Large scale reaction;

With water; citric acid; In 1-methyl-pyrrolidin-2-one; at 25 ℃; pH=4; Large scale reaction;

DOI:10.1021/op900104g

Reference yield:

silver cyanate (3315-16-0) + trans-tert-butyl 4-hydroxycyclohexylcarbamate (111300-06-2) + (3R,3aS,4R,SR,7S,9R,9aR,12R)-3-methoxy-4,7,9,12-tetramethyl-8-oxo-7-vinyldecahydro-4,9a-propanocyclopenta[8]annulen-5-yl carbonochloridate (193536-85-5) → trans-4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)cyclohexyl (1R,2R,4S,6R,7R,9R)-4-ethenyl-2,4,7,14-tetramethyl-9-(methyloxy)-3-oxotricyclo[5.4.3.0(1,8)]tetradec-6-yl imidodicarbonate (937369-86-3)

Guidance literature:

With pyridine; In dichloromethane;

DOI:10.1021/op900104g

Reference yield: 83.0%

trans-4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)cyclohexyl (1R,2R,4S,6R,7R,9R)-4-ethenyl-2,4,7,14-tetramethyl-9-(methyloxy)-3-oxotricyclo[5.4.3.0(1,8)]tetradec-6-yl imidodicarbonate (937369-86-3) → trans-4-aminocyclohexyl (1S,2R,3S,4S,6R,7R,8R)-4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0(1,8)]tetradec-6-yl imidodicarbonate (937369-81-8)

Guidance literature:

trans-4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)cyclohexyl (1R,2R,4S,6R,7R,9R)-4-ethenyl-2,4,7,14-tetramethyl-9-(methyloxy)-3-oxotricyclo[5.4.3.0(1,8)]tetradec-6-yl imidodicarbonate; With hydrogenchloride; water; In toluene; at 10 - 25 ℃; for 2.5h; Large scale reaction;

With ammonium hydroxide; In water; ethyl acetate; isopropyl alcohol; at 15 - 30 ℃; for 2h; Large scale reaction;

DOI:10.1021/op900104g

upstream raw materials:

(3R,3aS,4R,5R,7S,9R,9aR,12R)-3-methoxy-4,7,9,12-tetramethyl-8-oxo-7-vinyldecahydro-4,9a-propanocyclopenta[8]annulen-5-yl carbamate

C₁₅H₂₃N₃O₄

silver cyanate

trans-tert-butyl 4-hydroxycyclohexylcarbamate

Downstream raw materials:

trans-4-aminocyclohexyl (1S,2R,3S,4S,6R,7R,8R)-4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0(1,8)]tetradec-6-yl imidodicarbonate

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