4-{[(1R,2R,5R,10S,13R,14R,17S,19R)-5-({[(3-chlorophenyl)methyl]carbamoyl}(oxo)methyl)-1,2,14,18,18-pentamethyl-7-oxo-8-(propan-2-yl)pentacyclo[11.8.0.0^2,10.0^5,9.0^14,19]henicos-8-en-17-yl]oxy}-2,2-dimethyl-4-oxobutanoic acid

Base Information

• Chemical Name: 4-{[(1R,2R,5R,10S,13R,14R,17S,19R)-5-({[(3-chlorophenyl)methyl]carbamoyl}(oxo)methyl)-1,2,14,18,18-pentamethyl-7-oxo-8-(propan-2-yl)pentacyclo[11.8.0.0^2,10.0^5,9.0^14,19]henicos-8-en-17-yl]oxy}-2,2-dimethyl-4-oxobutanoic acid
• CAS No.: 1326312-49-5
• Molecular Formula: C₄₄H₆₀ClNO₇
• Molecular Weight: 750.416
• Mol file: 1326312-49-5.mol

Synonyms:

Chemical Property of 4-{[(1R,2R,5R,10S,13R,14R,17S,19R)-5-({[(3-chlorophenyl)methyl]carbamoyl}(oxo)methyl)-1,2,14,18,18-pentamethyl-7-oxo-8-(propan-2-yl)pentacyclo[11.8.0.0^2,10.0^5,9.0^14,19]henicos-8-en-17-yl]oxy}-2,2-dimethyl-4-oxobutanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-{[(1R,2R,5R,10S,13R,14R,17S,19R)-5-({[(3-chlorophenyl)methyl]carbamoyl}(oxo)methyl)-1,2,14,18,18-pentamethyl-7-oxo-8-(propan-2-yl)pentacyclo[11.8.0.0^2,10.0^5,9.0^14,19]henicos-8-en-17-yl]oxy}-2,2-dimethyl-4-oxobutanoic acid

There total 8 articles about 4-{[(1R,2R,5R,10S,13R,14R,17S,19R)-5-({[(3-chlorophenyl)methyl]carbamoyl}(oxo)methyl)-1,2,14,18,18-pentamethyl-7-oxo-8-(propan-2-yl)pentacyclo[11.8.0.0^2,10.0^5,9.0^14,19]henicos-8-en-17-yl]oxy}-2,2-dimethyl-4-oxobutanoic acid 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:

betulin (473-98-3) → 4-{[(1R,2R,5R,10S,13R,14R,17S,19R)-5-({[(3-chlorophenyl)methyl]carbamoyl}(oxo)methyl)-1,2,14,18,18-pentamethyl-7-oxo-8-(propan-2-yl)pentacyclo[11.8.0.02,10.05,9.014,19]henicos-8-en-17-yl]oxy}-2,2-dimethyl-4-oxobutanoic acid (1326312-49-5)

Guidance literature:

Multi-step reaction with 10 steps

1.1: toluene / 3 h / 100 °C

2.1: acetic anhydride; hydrogen bromide; acetic acid / toluene / 1.5 h / 105 °C

3.1: acetic anhydride; acetic acid; sodium dichromate; sodium acetate / toluene / 60 °C

4.1: potassium hydroxide / toluene; ethanol / 0.5 h / 20 °C

5.1: silica gel; pyridinium chlorochromate / dichloromethane / 2 h / 20 °C

6.1: triethylamine / 20 °C

7.1: Dess-Martin periodane / dichloromethane / 0.67 h / 20 °C

8.1: sodium nitrite; acetic acid / dimethyl sulfoxide / 2 h / 40 °C

9.1: oxalyl dichloride / dichloromethane / 20 °C

9.2: 20 °C

9.3: 20 °C

10.1: dmap; pyridine

With pyridine; dmap; sodium dichromate; oxalyl dichloride; hydrogen bromide; sodium acetate; acetic anhydride; silica gel; Dess-Martin periodane; acetic acid; triethylamine; pyridinium chlorochromate; potassium hydroxide; sodium nitrite; In ethanol; dichloromethane; dimethyl sulfoxide; toluene; 6.1: |Henry Nitro Aldol Condensation / 7.1: |Dess-Martin Oxidation;

DOI:10.1016/j.bmcl.2017.04.042

Reference yield:

C33H48O6 (1326312-00-8) → 4-{[(1R,2R,5R,10S,13R,14R,17S,19R)-5-({[(3-chlorophenyl)methyl]carbamoyl}(oxo)methyl)-1,2,14,18,18-pentamethyl-7-oxo-8-(propan-2-yl)pentacyclo[11.8.0.02,10.05,9.014,19]henicos-8-en-17-yl]oxy}-2,2-dimethyl-4-oxobutanoic acid (1326312-49-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: oxalyl dichloride / dichloromethane / 20 °C

1.2: 20 °C

1.3: 20 °C

2.1: dmap; pyridine

With pyridine; dmap; oxalyl dichloride; In dichloromethane;

DOI:10.1016/j.bmcl.2017.04.042

Reference yield:

((3aS,5aR,5bR,7aR,9S,11aR,11bR,13aS)-9-acetoxy-1-isopropyl-5a,5b,8,8,11a-pentamethyl-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-3a-yl)methyl acetate (55976-58-4) → 4-{[(1R,2R,5R,10S,13R,14R,17S,19R)-5-({[(3-chlorophenyl)methyl]carbamoyl}(oxo)methyl)-1,2,14,18,18-pentamethyl-7-oxo-8-(propan-2-yl)pentacyclo[11.8.0.02,10.05,9.014,19]henicos-8-en-17-yl]oxy}-2,2-dimethyl-4-oxobutanoic acid (1326312-49-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: acetic anhydride; acetic acid; sodium dichromate; sodium acetate / toluene / 60 °C

2.1: potassium hydroxide / toluene; ethanol / 0.5 h / 20 °C

3.1: silica gel; pyridinium chlorochromate / dichloromethane / 2 h / 20 °C

4.1: triethylamine / 20 °C

5.1: Dess-Martin periodane / dichloromethane / 0.67 h / 20 °C

6.1: sodium nitrite; acetic acid / dimethyl sulfoxide / 2 h / 40 °C

7.1: oxalyl dichloride / dichloromethane / 20 °C

7.2: 20 °C

7.3: 20 °C

8.1: dmap; pyridine

With pyridine; dmap; sodium dichromate; oxalyl dichloride; sodium acetate; acetic anhydride; silica gel; Dess-Martin periodane; acetic acid; triethylamine; pyridinium chlorochromate; potassium hydroxide; sodium nitrite; In ethanol; dichloromethane; dimethyl sulfoxide; toluene; 4.1: |Henry Nitro Aldol Condensation / 5.1: |Dess-Martin Oxidation;

DOI:10.1016/j.bmcl.2017.04.042

upstream raw materials:

2,2-dimethylsuccinic anhydride

C₃₃H₄₈O₆

betulin

((3aS,5aR,5bR,7aR,9S,11aR,11bR,13aS)-9-acetoxy-1-isopropyl-5a,5b,8,8,11a-pentamethyl-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-3a-yl)methyl acetate