(R)-2-[(3S,4R,5S,8S)-8-(3-Benzyloxy-phenyl)-4-hydroxy-8-methoxy-3,5-dimethyl-oct-1-ynyl]-3,3,5-trimethyl-6-oxo-cyclohex-1-enecarboxylic acid

Base Information

• Chemical Name: (R)-2-[(3S,4R,5S,8S)-8-(3-Benzyloxy-phenyl)-4-hydroxy-8-methoxy-3,5-dimethyl-oct-1-ynyl]-3,3,5-trimethyl-6-oxo-cyclohex-1-enecarboxylic acid
• CAS No.: 165069-63-6
• Molecular Formula: C₃₄H₄₂O₆
• Molecular Weight: 546.704
• Mol file: 165069-63-6.mol

Synonyms:

Chemical Property of (R)-2-[(3S,4R,5S,8S)-8-(3-Benzyloxy-phenyl)-4-hydroxy-8-methoxy-3,5-dimethyl-oct-1-ynyl]-3,3,5-trimethyl-6-oxo-cyclohex-1-enecarboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-[(3S,4R,5S,8S)-8-(3-Benzyloxy-phenyl)-4-hydroxy-8-methoxy-3,5-dimethyl-oct-1-ynyl]-3,3,5-trimethyl-6-oxo-cyclohex-1-enecarboxylic acid

There total 20 articles about (R)-2-[(3S,4R,5S,8S)-8-(3-Benzyloxy-phenyl)-4-hydroxy-8-methoxy-3,5-dimethyl-oct-1-ynyl]-3,3,5-trimethyl-6-oxo-cyclohex-1-enecarboxylic 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:

(R)-5-Benzyloxymethoxy-2,2,4-trimethyl-pentanoic acid ethyl ester (159751-62-9) → (R)-2-[(3S,4R,5S,8S)-8-(3-Benzyloxy-phenyl)-4-hydroxy-8-methoxy-3,5-dimethyl-oct-1-ynyl]-3,3,5-trimethyl-6-oxo-cyclohex-1-enecarboxylic acid (165069-63-6)

Guidance literature:

Multi-step reaction with 13 steps

1: 92 percent / H₂ / Pd-black / ethanol

2: (COCl)2, Et₃N, DMSO / CH₂Cl₂

3: BF₃*OEt₂ / CH₂Cl₂

4: 93 percent / LiAlH₄ / diethyl ether

5: 98 percent / imidazole / dimethylformamide

6: 99 percent / t-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide

7: 93 percent / n-Bu₄NF / tetrahydrofuran

8: 92 percent / SO₃*pyridine, Et₃N, DMSO / CH₂Cl₂

9: 93 percent / n-BuLi / tetrahydrofuran

10: 87 percent / SO₃*pyridine, DMSO, Et₃N / CH₂Cl₂

11: 85 percent / NCS, AgNO₃, H₂O / acetonitrile

12: 27 percent / H₂O, TFA / CHCl₃

13: NaClO₂, NaH₂PO₄, 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O

With 1H-imidazole; sodium chlorite; sodium dihydrogenphosphate; N-chloro-succinimide; lithium aluminium tetrahydride; n-butyllithium; 2-methyl-but-2-ene; oxalyl dichloride; pyridine-SO₃ complex; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; hydrogen; tert.-butyl lithium; silver nitrate; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; palladium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;

DOI:10.1016/S0040-4039(00)73355-7

Reference yield:

(R)-5-Hydroxy-2,2,4-trimethyl-pentanoic acid ethyl ester (159751-63-0) → (R)-2-[(3S,4R,5S,8S)-8-(3-Benzyloxy-phenyl)-4-hydroxy-8-methoxy-3,5-dimethyl-oct-1-ynyl]-3,3,5-trimethyl-6-oxo-cyclohex-1-enecarboxylic acid (165069-63-6)

Guidance literature:

Multi-step reaction with 12 steps

1: (COCl)2, Et₃N, DMSO / CH₂Cl₂

2: BF₃*OEt₂ / CH₂Cl₂

3: 93 percent / LiAlH₄ / diethyl ether

4: 98 percent / imidazole / dimethylformamide

5: 99 percent / t-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide

6: 93 percent / n-Bu₄NF / tetrahydrofuran

7: 92 percent / SO₃*pyridine, Et₃N, DMSO / CH₂Cl₂

8: 93 percent / n-BuLi / tetrahydrofuran

9: 87 percent / SO₃*pyridine, DMSO, Et₃N / CH₂Cl₂

10: 85 percent / NCS, AgNO₃, H₂O / acetonitrile

11: 27 percent / H₂O, TFA / CHCl₃

12: NaClO₂, NaH₂PO₄, 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O

With 1H-imidazole; sodium chlorite; sodium dihydrogenphosphate; N-chloro-succinimide; lithium aluminium tetrahydride; n-butyllithium; 2-methyl-but-2-ene; oxalyl dichloride; pyridine-SO₃ complex; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; tert.-butyl lithium; silver nitrate; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;

DOI:10.1016/S0040-4039(00)73355-7

Reference yield:

(R)-4-[1,3]Dithian-2-yl-2,2-dimethyl-pentan-1-ol (159751-65-2) → (R)-2-[(3S,4R,5S,8S)-8-(3-Benzyloxy-phenyl)-4-hydroxy-8-methoxy-3,5-dimethyl-oct-1-ynyl]-3,3,5-trimethyl-6-oxo-cyclohex-1-enecarboxylic acid (165069-63-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 98 percent / imidazole / dimethylformamide

2: 99 percent / t-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide

3: 93 percent / n-Bu₄NF / tetrahydrofuran

4: 92 percent / SO₃*pyridine, Et₃N, DMSO / CH₂Cl₂

5: 93 percent / n-BuLi / tetrahydrofuran

6: 87 percent / SO₃*pyridine, DMSO, Et₃N / CH₂Cl₂

7: 85 percent / NCS, AgNO₃, H₂O / acetonitrile

8: 27 percent / H₂O, TFA / CHCl₃

9: NaClO₂, NaH₂PO₄, 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O

With 1H-imidazole; sodium chlorite; sodium dihydrogenphosphate; N-chloro-succinimide; n-butyllithium; 2-methyl-but-2-ene; pyridine-SO₃ complex; tetrabutyl ammonium fluoride; water; tert.-butyl lithium; silver nitrate; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;

DOI:10.1016/S0040-4039(00)73355-7

upstream raw materials:

(R)-2-[(3S,4R,5S,8S)-8-(3-Benzyloxy-phenyl)-4-hydroxy-8-methoxy-3,5-dimethyl-oct-1-ynyl]-3,3,5-trimethyl-6-oxo-cyclohex-1-enecarbaldehyde

(R)-4-[1,3]Dithian-2-yl-2,2-dimethyl-pentan-1-ol

(R)-5-Hydroxy-2,2,4-trimethyl-pentanoic acid ethyl ester

(R)-4-[2-(2,2-Dimethoxy-ethyl)-[1,3]dithian-2-yl]-2,2-dimethyl-pentan-1-ol