[(1S,2S)-4'-((R)-2-Acetoxy-1-methyl-ethyl)-5'-bromo-1,3,3-trimethyl-3',6'-dioxo-bicyclohexyl-1',4'-dien-2-yl]-acetic acid

Base Information

• Chemical Name: [(1S,2S)-4'-((R)-2-Acetoxy-1-methyl-ethyl)-5'-bromo-1,3,3-trimethyl-3',6'-dioxo-bicyclohexyl-1',4'-dien-2-yl]-acetic acid
• CAS No.: 81752-78-5
• Molecular Formula: C₂₂H₂₉BrO₆
• Molecular Weight: 469.373
• Mol file: 81752-78-5.mol

Synonyms:

Chemical Property of [(1S,2S)-4'-((R)-2-Acetoxy-1-methyl-ethyl)-5'-bromo-1,3,3-trimethyl-3',6'-dioxo-bicyclohexyl-1',4'-dien-2-yl]-acetic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(1S,2S)-4'-((R)-2-Acetoxy-1-methyl-ethyl)-5'-bromo-1,3,3-trimethyl-3',6'-dioxo-bicyclohexyl-1',4'-dien-2-yl]-acetic acid

There total 10 articles about [(1S,2S)-4'-((R)-2-Acetoxy-1-methyl-ethyl)-5'-bromo-1,3,3-trimethyl-3',6'-dioxo-bicyclohexyl-1',4'-dien-2-yl]-acetic 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:

[(1S,2S)-4'-((S)-2-Acetoxy-1-methyl-ethyl)-4',5'-dibromo-1,3,3-trimethyl-3',6'-dioxo-bicyclohexyl-1'-en-2-yl]-acetic acid (81752-77-4) → [(1S,2S)-4'-((R)-2-Acetoxy-1-methyl-ethyl)-5'-bromo-1,3,3-trimethyl-3',6'-dioxo-bicyclohexyl-1',4'-dien-2-yl]-acetic acid (81752-78-5)

Guidance literature:

With diethylamine; In diethyl ether; Yield given;

Reference yield:

13-(1'-methenylethyl)-12-methoxy-podocarpane-8,11,13-triene (10064-25-2) → [(1S,2S)-4'-((R)-2-Acetoxy-1-methyl-ethyl)-5'-bromo-1,3,3-trimethyl-3',6'-dioxo-bicyclohexyl-1',4'-dien-2-yl]-acetic acid (81752-78-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) borane-methyl sulfide,2.) H₂O₂

2: pyridine

3: CrO₃ / pyridine

4: Ac₂O, H₂SO₄, H₂O₂

5: Br₂, HOAc

6: Et₂NH / diethyl ether

With chromium(VI) oxide; dimethylsulfide borane complex; sulfuric acid; dihydrogen peroxide; bromine; acetic anhydride; acetic acid; diethylamine; In pyridine; diethyl ether;

Reference yield:

methyl 13-isopropenyl-12-methoxypodocarpa-8,11,13-trien-19-oate (24099-80-7) → [(1S,2S)-4'-((R)-2-Acetoxy-1-methyl-ethyl)-5'-bromo-1,3,3-trimethyl-3',6'-dioxo-bicyclohexyl-1',4'-dien-2-yl]-acetic acid (81752-78-5)

Guidance literature:

Multi-step reaction with 9 steps

1: LiAlH₄ / diethyl ether

2: CrO₃ / pyridine

3: Wolf-Kishner reduction

4: 1.) borane-methyl sulfide,2.) H₂O₂

5: pyridine

6: CrO₃ / pyridine

7: Ac₂O, H₂SO₄, H₂O₂

8: Br₂, HOAc

9: Et₂NH / diethyl ether

With chromium(VI) oxide; lithium aluminium tetrahydride; dimethylsulfide borane complex; sulfuric acid; dihydrogen peroxide; bromine; acetic anhydride; acetic acid; diethylamine; In pyridine; diethyl ether;

upstream raw materials:

2-<2-<4-(2-acetoxy-1(R)-methylethyl)-benzoquinone-2,5>yl-2,6,6-trimethylcyclohexyl>ethanoic acid

[(1S,2S)-4'-((S)-2-Acetoxy-1-methyl-ethyl)-4',5'-dibromo-1,3,3-trimethyl-3',6'-dioxo-bicyclohexyl-1'-en-2-yl]-acetic acid

13-(1'-methenylethyl)-12-methoxy-podocarpane-8,11,13-triene

methyl 13-isopropenyl-12-methoxypodocarpa-8,11,13-trien-19-oate

Downstream raw materials:

2-<2-<3-hydroxy-4-(2-hydroxy-1-methylethyl)-benzoquinone-2,5>yl-2,6,6-trimethylcyclohexyl>ethanoic acid

[(1S,2S)-4'-((R)-2-Hydroxy-1-methyl-ethyl)-5'-methoxy-1,3,3-trimethyl-3',6'-dioxo-bicyclohexyl-1',4'-dien-2-yl]-acetic acid