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

Base Information

• Chemical Name: (R)-2-[(3S,4R,5S,8S)-8-(3-Benzyloxy-phenyl)-8-methoxy-4-methoxymethoxy-3,5-dimethyl-oct-1-ynyl]-3,3,5-trimethyl-6-oxo-cyclohex-1-enecarbaldehyde
• CAS No.: 159751-77-6
• Molecular Formula: C₃₆H₄₆O₆
• Molecular Weight: 574.758

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

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

There total 16 articles about (R)-2-[(3S,4R,5S,8S)-8-(3-Benzyloxy-phenyl)-8-methoxy-4-methoxymethoxy-3,5-dimethyl-oct-1-ynyl]-3,3,5-trimethyl-6-oxo-cyclohex-1-enecarbaldehyde 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: 56.0%

(4R,10S,11R,12S,15S)-15-(3-Benzyloxy-phenyl)-1,1,15-trimethoxy-11-methoxymethoxy-4,6,6,10,12-pentamethyl-pentadec-8-yne-3,7-dione (159751-76-5) → (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 (159751-78-7) + (R)-2-[(3S,4R,5S,8S)-8-(3-Benzyloxy-phenyl)-8-methoxy-4-methoxymethoxy-3,5-dimethyl-oct-1-ynyl]-3,3,5-trimethyl-6-oxo-cyclohex-1-enecarbaldehyde (159751-77-6)

Guidance literature:

With water; trifluoroacetic acid; In chloroform;

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

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)-8-methoxy-4-methoxymethoxy-3,5-dimethyl-oct-1-ynyl]-3,3,5-trimethyl-6-oxo-cyclohex-1-enecarbaldehyde (159751-77-6)

Guidance literature:

Multi-step reaction with 12 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: 56 percent / H₂O, TFA / CHCl₃

With 1H-imidazole; N-chloro-succinimide; lithium aluminium tetrahydride; n-butyllithium; 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; N,N-dimethyl-formamide; acetonitrile;

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)-8-methoxy-4-methoxymethoxy-3,5-dimethyl-oct-1-ynyl]-3,3,5-trimethyl-6-oxo-cyclohex-1-enecarbaldehyde (159751-77-6)

Guidance literature:

Multi-step reaction with 8 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: 56 percent / H₂O, TFA / CHCl₃

With 1H-imidazole; N-chloro-succinimide; n-butyllithium; 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; N,N-dimethyl-formamide; acetonitrile;

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

upstream raw materials:

(4R,10S,11R,12S,15S)-15-(3-Benzyloxy-phenyl)-1,1,15-trimethoxy-11-methoxymethoxy-4,6,6,10,12-pentamethyl-pentadec-8-yne-3,7-dione

(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

Downstream raw materials:

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

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

(R)-2-[(Z)-(3S,4R,5S,8S)-8-(3-Benzyloxy-phenyl)-8-methoxy-4-methoxymethoxy-3,5-dimethyl-oct-1-enyl]-3,3,5-trimethyl-6-oxo-cyclohex-1-enecarboxylic acid methyl ester

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