tert-butyl 4-chlorobenzyl(2-((3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-9-hydroxy-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-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)-2-oxoethyl)carbamate

Base Information

• Chemical Name: tert-butyl 4-chlorobenzyl(2-((3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-9-hydroxy-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-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)-2-oxoethyl)carbamate
• CAS No.: 1326312-10-0
• Molecular Formula: C₄₃H₆₂ClNO₅
• Molecular Weight: 708.422

Synonyms:tert-butyl 4-chlorobenzyl(2-((3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-9-hydroxy-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-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)-2-oxoethyl)carbamate

Chemical Property of tert-butyl 4-chlorobenzyl(2-((3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-9-hydroxy-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-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)-2-oxoethyl)carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of tert-butyl 4-chlorobenzyl(2-((3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-9-hydroxy-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-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)-2-oxoethyl)carbamate

There total 13 articles about tert-butyl 4-chlorobenzyl(2-((3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-9-hydroxy-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-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)-2-oxoethyl)carbamate 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: 62.0%

di-tert-butyl dicarbonate (24424-99-5) + (3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-(2-((4-chlorobenzyl)amino)acetyl)-9-hydroxy-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-2-one (1326312-09-7) → tert-butyl 4-chlorobenzyl(2-((3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-9-hydroxy-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-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)-2-oxoethyl)carbamate (1326312-10-0)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 1h;

Reference yield:

betulin diacetate (1721-69-3) → tert-butyl 4-chlorobenzyl(2-((3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-9-hydroxy-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-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)-2-oxoethyl)carbamate (1326312-10-0)

Guidance literature:

Multi-step reaction with 11 steps

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

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

3.1: potassium hydroxide / toluene; ethanol / 1 h / 20 °C

3.2: pH 7

4.1: silica gel; pyridinium chlorochromate / dichloromethane / 1 h / 20 °C

5.1: triethylamine / dichloromethane / 20 °C

6.1: sodium tetrahydroborate; methanol; nickel(II) chloride hexahydrate / 0.5 h / 0 °C

7.1: zinc(II) chloride / methanol / 2 h / 20 °C

7.2: 2 h / 20 °C

8.1: triethylamine / 20 °C

9.1: silica gel; pyridinium chlorochromate / dichloromethane / 8 h / 20 °C

10.1: hydrogenchloride; water / 1,4-dioxane / 20 °C

11.1: triethylamine / dichloromethane / 1 h / 20 °C

With hydrogenchloride; methanol; sodium tetrahydroborate; sodium dichromate dihydrate; nickel(II) chloride hexahydrate; water; hydrogen bromide; sodium acetate; acetic anhydride; silica gel; acetic acid; triethylamine; pyridinium chlorochromate; potassium hydroxide; zinc(II) chloride; In 1,4-dioxane; methanol; ethanol; dichloromethane; toluene;

Reference yield:

betulin (473-98-3) → tert-butyl 4-chlorobenzyl(2-((3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-9-hydroxy-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-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)-2-oxoethyl)carbamate (1326312-10-0)

Guidance literature:

Multi-step reaction with 12 steps

1.1: dmap; triethylamine / dichloromethane / Reflux

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

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

4.1: potassium hydroxide / toluene; ethanol / 1 h / 20 °C

4.2: pH 7

5.1: silica gel; pyridinium chlorochromate / dichloromethane / 1 h / 20 °C

6.1: triethylamine / dichloromethane / 20 °C

7.1: sodium tetrahydroborate; methanol; nickel(II) chloride hexahydrate / 0.5 h / 0 °C

8.1: zinc(II) chloride / methanol / 2 h / 20 °C

8.2: 2 h / 20 °C

9.1: triethylamine / 20 °C

10.1: silica gel; pyridinium chlorochromate / dichloromethane / 8 h / 20 °C

11.1: hydrogenchloride; water / 1,4-dioxane / 20 °C

12.1: triethylamine / dichloromethane / 1 h / 20 °C

With hydrogenchloride; methanol; dmap; sodium tetrahydroborate; sodium dichromate dihydrate; nickel(II) chloride hexahydrate; water; hydrogen bromide; sodium acetate; acetic anhydride; silica gel; acetic acid; triethylamine; pyridinium chlorochromate; potassium hydroxide; zinc(II) chloride; In 1,4-dioxane; methanol; ethanol; dichloromethane; toluene;

upstream raw materials:

di-tert-butyl dicarbonate

(3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-(2-((4-chlorobenzyl)amino)acetyl)-9-hydroxy-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-2-one

betulin diacetate

betulin

Downstream raw materials:

C₄₉H₇₀ClNO₈

4-{[(3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-[{[(4-chlorophenyl)methyl]amino}acetyl]-5a,5b,8,8,11a-pentamethyl-1-(1-methylethyl)-2-oxo-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-9-yl]oxy}-2,2-dimethyl-4-oxo-butanoic acid

4-(((3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-((R)-1-acetoxy-2-((4-chlorobenzyl)amino)ethyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-9-yl)oxy)-2,2-dimethyl-4-oxobutanoic acid trifluoroacetate

4-((3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-((R)-1-acetoxy-2-((tert-butoxycarbonyl)(4-chlorobenzyl)amino)ethyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-9-yl) 1-tert-butyl 2,2-dimethylsuccinate

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