(R)-2-(Cyclohexanecarbonyl-amino)-propionic acid (6E,8E,10E,16Z)-(5R,13S,14S,15R)-15-(tert-butyl-dimethyl-silanyloxy)-5,22,24-trimethoxy-14,16-dimethyl-3-oxo-2-aza-bicyclo[18.3.1]tetracosa-1⁽²³⁾,6,8,10,16,20⁽²⁴⁾,21-heptaen-13-yl ester

Base Information

• Chemical Name: (R)-2-(Cyclohexanecarbonyl-amino)-propionic acid (6E,8E,10E,16Z)-(5R,13S,14S,15R)-15-(tert-butyl-dimethyl-silanyloxy)-5,22,24-trimethoxy-14,16-dimethyl-3-oxo-2-aza-bicyclo[18.3.1]tetracosa-1⁽²³⁾,6,8,10,16,20⁽²⁴⁾,21-heptaen-13-yl ester
• CAS No.: 198758-00-8
• Molecular Formula: C₄₄H₆₈N₂O₈Si
• Molecular Weight: 781.118

Synonyms:(R)-2-(Cyclohexanecarbonyl-amino)-propionic acid (6E,8E,10E,16Z)-(5R,13S,14S,15R)-15-(tert-butyl-dimethyl-silanyloxy)-5,22,24-trimethoxy-14,16-dimethyl-3-oxo-2-aza-bicyclo[18.3.1]tetracosa-1⁽²³⁾,6,8,10,16,20⁽²⁴⁾,21-heptaen-13-yl ester

Chemical Property of (R)-2-(Cyclohexanecarbonyl-amino)-propionic acid (6E,8E,10E,16Z)-(5R,13S,14S,15R)-15-(tert-butyl-dimethyl-silanyloxy)-5,22,24-trimethoxy-14,16-dimethyl-3-oxo-2-aza-bicyclo[18.3.1]tetracosa-1⁽²³⁾,6,8,10,16,20⁽²⁴⁾,21-heptaen-13-yl ester

Chemical Property:

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Technology Process of (R)-2-(Cyclohexanecarbonyl-amino)-propionic acid (6E,8E,10E,16Z)-(5R,13S,14S,15R)-15-(tert-butyl-dimethyl-silanyloxy)-5,22,24-trimethoxy-14,16-dimethyl-3-oxo-2-aza-bicyclo[18.3.1]tetracosa-1⁽²³⁾,6,8,10,16,20⁽²⁴⁾,21-heptaen-13-yl ester

There total 25 articles about (R)-2-(Cyclohexanecarbonyl-amino)-propionic acid (6E,8E,10E,16Z)-(5R,13S,14S,15R)-15-(tert-butyl-dimethyl-silanyloxy)-5,22,24-trimethoxy-14,16-dimethyl-3-oxo-2-aza-bicyclo[18.3.1]tetracosa-1⁽²³⁾,6,8,10,16,20⁽²⁴⁾,21-heptaen-13-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:

2,5-dimethoxy-3-nitrobenzaldehyde (74422-90-5) → (R)-2-(Cyclohexanecarbonyl-amino)-propionic acid (6E,8E,10E,16Z)-(5R,13S,14S,15R)-15-(tert-butyl-dimethyl-silanyloxy)-5,22,24-trimethoxy-14,16-dimethyl-3-oxo-2-aza-bicyclo[18.3.1]tetracosa-1(23),6,8,10,16,20(24),21-heptaen-13-yl ester (198758-00-8)

Guidance literature:

Multi-step reaction with 17 steps

1.1: 100 percent / BH₃*THF

2.1: 80 percent / CBr₄; PPh₃

3.1: 85 percent

4.1: 100 percent / H₂ / Pd/C

5.1: 70 percent / Me₃Al / benzene

6.1: 98 percent / imidazole

7.1: LHMDS / tetrahydrofuran / -78 °C

7.2: 80 percent / tetrahydrofuran

8.1: 98 percent / Na(Hg); Na₂HPO₄

9.1: 95 percent / HF*Pyr / pyridine

10.1: 80 percent / Pyr*SO₃ / dimethylsulfoxide

11.1: 90 percent / PPTS / acetone

12.1: 70 percent / CrCl₂

13.1: Pd(MeCN)2Cl₂ / dimethylformamide; tetrahydrofuran

14.1: pTsOH / methanol

15.1: DMAP / CH₂Cl₂ / -78 °C

16.1: Et₂NH / CH₂Cl₂

17.1: BOP; Et₃N / CH₂Cl₂

With 1H-imidazole; chromium dichloride; dmap; disodium hydrogenphosphate; sodium amalgam; borane-THF; carbon tetrabromide; hydrogen; trimethylaluminum; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; toluene-4-sulfonic acid; pyridine hydrogenfluoride; diethylamine; triethylamine; triphenylphosphine; lithium hexamethyldisilazane; dichloro bis(acetonitrile) palladium(II); palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; benzene; 1.1: Reduction / 2.1: Bromination / 3.1: Substitution / 4.1: Catalytic hydrogenation / 5.1: Weinreb-type amidation / 6.1: silylation / 7.1: Metallation / 7.2: Alkylation / 8.1: Reduction / 9.1: desilylation / 10.1: Parikh-Doering oxidation / 11.1: Hydrolysis / 12.1: Condensation / 13.1: Cyclization / 14.1: desilylation / 15.1: Esterification / 16.1: deacylation / 17.1: Acylation;

DOI:10.1021/jo971793j

Reference yield:

(2,5-dimethoxy-3-nitrophenyl)methanol (198758-06-4) → (R)-2-(Cyclohexanecarbonyl-amino)-propionic acid (6E,8E,10E,16Z)-(5R,13S,14S,15R)-15-(tert-butyl-dimethyl-silanyloxy)-5,22,24-trimethoxy-14,16-dimethyl-3-oxo-2-aza-bicyclo[18.3.1]tetracosa-1(23),6,8,10,16,20(24),21-heptaen-13-yl ester (198758-00-8)

Guidance literature:

Multi-step reaction with 16 steps

1.1: 80 percent / CBr₄; PPh₃

2.1: 85 percent

3.1: 100 percent / H₂ / Pd/C

4.1: 70 percent / Me₃Al / benzene

5.1: 98 percent / imidazole

6.1: LHMDS / tetrahydrofuran / -78 °C

6.2: 80 percent / tetrahydrofuran

7.1: 98 percent / Na(Hg); Na₂HPO₄

8.1: 95 percent / HF*Pyr / pyridine

9.1: 80 percent / Pyr*SO₃ / dimethylsulfoxide

10.1: 90 percent / PPTS / acetone

11.1: 70 percent / CrCl₂

12.1: Pd(MeCN)2Cl₂ / dimethylformamide; tetrahydrofuran

13.1: pTsOH / methanol

14.1: DMAP / CH₂Cl₂ / -78 °C

15.1: Et₂NH / CH₂Cl₂

16.1: BOP; Et₃N / CH₂Cl₂

With 1H-imidazole; chromium dichloride; dmap; disodium hydrogenphosphate; sodium amalgam; carbon tetrabromide; hydrogen; trimethylaluminum; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; toluene-4-sulfonic acid; pyridine hydrogenfluoride; diethylamine; triethylamine; triphenylphosphine; lithium hexamethyldisilazane; dichloro bis(acetonitrile) palladium(II); palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; benzene; 1.1: Bromination / 2.1: Substitution / 3.1: Catalytic hydrogenation / 4.1: Weinreb-type amidation / 5.1: silylation / 6.1: Metallation / 6.2: Alkylation / 7.1: Reduction / 8.1: desilylation / 9.1: Parikh-Doering oxidation / 10.1: Hydrolysis / 11.1: Condensation / 12.1: Cyclization / 13.1: desilylation / 14.1: Esterification / 15.1: deacylation / 16.1: Acylation;

DOI:10.1021/jo971793j

Reference yield:

1-(bromomethyl)-2,5-dimethoxy-3-nitrobenzene (198758-07-5) → (R)-2-(Cyclohexanecarbonyl-amino)-propionic acid (6E,8E,10E,16Z)-(5R,13S,14S,15R)-15-(tert-butyl-dimethyl-silanyloxy)-5,22,24-trimethoxy-14,16-dimethyl-3-oxo-2-aza-bicyclo[18.3.1]tetracosa-1(23),6,8,10,16,20(24),21-heptaen-13-yl ester (198758-00-8)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 85 percent

2.1: 100 percent / H₂ / Pd/C

3.1: 70 percent / Me₃Al / benzene

4.1: 98 percent / imidazole

5.1: LHMDS / tetrahydrofuran / -78 °C

5.2: 80 percent / tetrahydrofuran

6.1: 98 percent / Na(Hg); Na₂HPO₄

7.1: 95 percent / HF*Pyr / pyridine

8.1: 80 percent / Pyr*SO₃ / dimethylsulfoxide

9.1: 90 percent / PPTS / acetone

10.1: 70 percent / CrCl₂

11.1: Pd(MeCN)2Cl₂ / dimethylformamide; tetrahydrofuran

12.1: pTsOH / methanol

13.1: DMAP / CH₂Cl₂ / -78 °C

14.1: Et₂NH / CH₂Cl₂

15.1: BOP; Et₃N / CH₂Cl₂

With 1H-imidazole; chromium dichloride; dmap; disodium hydrogenphosphate; sodium amalgam; hydrogen; trimethylaluminum; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; toluene-4-sulfonic acid; pyridine hydrogenfluoride; diethylamine; triethylamine; lithium hexamethyldisilazane; dichloro bis(acetonitrile) palladium(II); palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; benzene; 1.1: Substitution / 2.1: Catalytic hydrogenation / 3.1: Weinreb-type amidation / 4.1: silylation / 5.1: Metallation / 5.2: Alkylation / 6.1: Reduction / 7.1: desilylation / 8.1: Parikh-Doering oxidation / 9.1: Hydrolysis / 10.1: Condensation / 11.1: Cyclization / 12.1: desilylation / 13.1: Esterification / 14.1: deacylation / 15.1: Acylation;

DOI:10.1021/jo971793j

upstream raw materials:

Cyclohexanecarboxylic acid

2,5-dimethoxy-3-nitrobenzaldehyde

(2,5-dimethoxy-3-nitrophenyl)methanol

1-(bromomethyl)-2,5-dimethoxy-3-nitrobenzene

Downstream raw materials:

(+)-mycotrienin I

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