(S)-2-Methyl-butyric acid (1S,3R,7S,8S,8aR)-3,7-dimethyl-8-(2-{(2S,4R)-4-[2-(4-nitro-phenyl)-acetoxy]-6-oxo-tetrahydro-pyran-2-yl}-ethyl)-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

Base Information

• Chemical Name: (S)-2-Methyl-butyric acid (1S,3R,7S,8S,8aR)-3,7-dimethyl-8-(2-{(2S,4R)-4-[2-(4-nitro-phenyl)-acetoxy]-6-oxo-tetrahydro-pyran-2-yl}-ethyl)-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester
• CAS No.: 105227-52-9
• Molecular Formula: C₃₂H₄₁NO₈
• Molecular Weight: 567.679
• Mol file: 105227-52-9.mol

Synonyms:

Chemical Property of (S)-2-Methyl-butyric acid (1S,3R,7S,8S,8aR)-3,7-dimethyl-8-(2-{(2S,4R)-4-[2-(4-nitro-phenyl)-acetoxy]-6-oxo-tetrahydro-pyran-2-yl}-ethyl)-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-Methyl-butyric acid (1S,3R,7S,8S,8aR)-3,7-dimethyl-8-(2-{(2S,4R)-4-[2-(4-nitro-phenyl)-acetoxy]-6-oxo-tetrahydro-pyran-2-yl}-ethyl)-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

There total 4 articles about (S)-2-Methyl-butyric acid (1S,3R,7S,8S,8aR)-3,7-dimethyl-8-(2-{(2S,4R)-4-[2-(4-nitro-phenyl)-acetoxy]-6-oxo-tetrahydro-pyran-2-yl}-ethyl)-1,2,3,7,8,8a-hexahydro-naphthalen-1-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:

6(R)-<2-<1,2,6,7,8,8a(R)-Hexahydro-2(S),6(R)-dimethyl-8(S)-<<2(S)-methylbutyryl>oxy>-1(S)-naphtyl>ethyl>-3,4,5,6-tetrahydro-4(R)-<(tert-butyldimethylsilyl)oxy>-2H-pyran-2-one (79691-11-5,82978-03-8) → (S)-2-Methyl-butyric acid (1S,3R,7S,8S,8aR)-3,7-dimethyl-8-(2-{(2S,4R)-4-[2-(4-nitro-phenyl)-acetoxy]-6-oxo-tetrahydro-pyran-2-yl}-ethyl)-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester (105227-52-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / methanol / 18 h / Heating

2: 68 percent / triethylamine, methanesulfonyl chloride / CH₂Cl₂ / 1.) 3 h, 2.) RT, 8 h

3: 68 percent / HOAc, tetra n-butylammonium fluoride / methanol / Ambient temperature

4: pyridine / Ambient temperature

With pyridine; tetrabutyl ammonium fluoride; acetic acid; methanesulfonyl chloride; triethylamine; In methanol; dichloromethane;

DOI:10.1021/jo00375a032

Reference yield:

N-benzyl 7-<1,2,6,7,8,8a(R)-hexahydro-2(S),6(R)-dimethyl-8(S)-<<2(S)-methylbutanoyl>oxy>-1(S)-naphthyl>-3(R)-<(tert-butyldimethylsilyl)oxy>-5(R)-hydroxyheptanoic acid amide (102963-74-6) → (S)-2-Methyl-butyric acid (1S,3R,7S,8S,8aR)-3,7-dimethyl-8-(2-{(2S,4R)-4-[2-(4-nitro-phenyl)-acetoxy]-6-oxo-tetrahydro-pyran-2-yl}-ethyl)-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester (105227-52-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 68 percent / triethylamine, methanesulfonyl chloride / CH₂Cl₂ / 1.) 3 h, 2.) RT, 8 h

2: 68 percent / HOAc, tetra n-butylammonium fluoride / methanol / Ambient temperature

3: pyridine / Ambient temperature

With pyridine; tetrabutyl ammonium fluoride; acetic acid; methanesulfonyl chloride; triethylamine; In methanol; dichloromethane;

DOI:10.1021/jo00375a032

Reference yield:

6(S)-<2-<8(S)-<<2(S)-methylbutanoyl>oxy>-2(S),6(R)-dimethyl-1,2,6,7,8,8a(R)-hexahydro-1(S)-naphthyl>ethyl>-4-(R)-<(tert-butyldimethylsilyl)oxy>-3,4,5,6-tetrahydro-2H-pyran-2-one (103063-54-3,82978-03-8) → (S)-2-Methyl-butyric acid (1S,3R,7S,8S,8aR)-3,7-dimethyl-8-(2-{(2S,4R)-4-[2-(4-nitro-phenyl)-acetoxy]-6-oxo-tetrahydro-pyran-2-yl}-ethyl)-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester (105227-52-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / HOAc, tetra n-butylammonium fluoride / methanol / Ambient temperature

2: pyridine / Ambient temperature

With pyridine; tetrabutyl ammonium fluoride; acetic acid; In methanol;

DOI:10.1021/jo00375a032

upstream raw materials:

lovastatin

4-nitrophenylacetyl chloride

6(R)-<2-<1,2,6,7,8,8a(R)-Hexahydro-2(S),6(R)-dimethyl-8(S)-<<2(S)-methylbutyryl>oxy>-1(S)-naphtyl>ethyl>-3,4,5,6-tetrahydro-4(R)-<(tert-butyldimethylsilyl)oxy>-2H-pyran-2-one

N-benzyl 7-<1,2,6,7,8,8a(R)-hexahydro-2(S),6(R)-dimethyl-8(S)-<<2(S)-methylbutanoyl>oxy>-1(S)-naphthyl>-3(R)-<(tert-butyldimethylsilyl)oxy>-5(R)-hydroxyheptanoic acid amide