(2R,4S)-4-{(Z)-(S)-5-[3-((S)-1-Hydroxy-propyl)-phenyl]-4-methyl-2-methylsulfanyl-pent-2-enyl}-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxolane-4-carboxylic acid methyl ester

Base Information

• Chemical Name: (2R,4S)-4-{(Z)-(S)-5-[3-((S)-1-Hydroxy-propyl)-phenyl]-4-methyl-2-methylsulfanyl-pent-2-enyl}-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxolane-4-carboxylic acid methyl ester
• CAS No.: 594855-08-0
• Molecular Formula: C₃₀H₄₀O₅S
• Molecular Weight: 512.711

Synonyms:

Chemical Property of (2R,4S)-4-{(Z)-(S)-5-[3-((S)-1-Hydroxy-propyl)-phenyl]-4-methyl-2-methylsulfanyl-pent-2-enyl}-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxolane-4-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4S)-4-{(Z)-(S)-5-[3-((S)-1-Hydroxy-propyl)-phenyl]-4-methyl-2-methylsulfanyl-pent-2-enyl}-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxolane-4-carboxylic acid methyl ester

There total 16 articles about (2R,4S)-4-{(Z)-(S)-5-[3-((S)-1-Hydroxy-propyl)-phenyl]-4-methyl-2-methylsulfanyl-pent-2-enyl}-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxolane-4-carboxylic acid methyl 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:

mesytaldehyde (487-68-3) → (2R,4S)-4-{(Z)-(S)-5-[3-((S)-1-Hydroxy-propyl)-phenyl]-4-methyl-2-methylsulfanyl-pent-2-enyl}-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxolane-4-carboxylic acid methyl ester (594855-08-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: camphorsulfonic acid; 4A molecular sieves; MgSO₄ / CHCl₃

2.1: lithium hexamethyldisilazide; HMPA / tetrahydrofuran

2.2: 53 percent / HMPA / tetrahydrofuran

3.1: tetrabutylammonium fluoride / tetrahydrofuran

4.1: benzene; methanol

With N,N,N,N,N,N-hexamethylphosphoric triamide; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; magnesium sulfate; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; chloroform; benzene;

DOI:10.1248/cpb.52.163

Reference yield:

(S)-1-(3'-bromophenyl)-1-propanol (224622-38-2) → (2R,4S)-4-{(Z)-(S)-5-[3-((S)-1-Hydroxy-propyl)-phenyl]-4-methyl-2-methylsulfanyl-pent-2-enyl}-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxolane-4-carboxylic acid methyl ester (594855-08-0)

Guidance literature:

Multi-step reaction with 14 steps

1.1: n-BuLi / tetrahydrofuran

1.2: 100 percent / tetrahydrofuran

2.1: 61 percent / imidazole / dimethylformamide

3.1: 92 percent / NaBH₄ / ethanol

4.1: 95 percent / NaH / tetrahydrofuran

5.1: 94 percent / n-Bu₃SnH / toluene

6.1: 70 percent / aq. p-TsOH / ethanol

7.1: 96 percent / (COCl)2; DMSO; TEA / CH₂Cl₂

8.1: lithium hexamethyldisilazide / tetrahydrofuran

8.2: 88 percent / tetrahydrofuran

9.1: 78 percent / MsCl; TEA; DBU / CH₂Cl₂; tetrahydrofuran

10.1: 82 percent / DIBAL-H / CH₂Cl₂

11.1: 100 percent / I₂; Ph₃P; imidazole / diethyl ether; acetonitrile

12.1: lithium hexamethyldisilazide; HMPA / tetrahydrofuran

12.2: 53 percent / HMPA / tetrahydrofuran

13.1: tetrabutylammonium fluoride / tetrahydrofuran

14.1: benzene; methanol

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; TEA; tetrabutyl ammonium fluoride; iodine; tri-n-butyl-tin hydride; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; benzene; 7.1: Swern oxidation;

DOI:10.1248/cpb.52.163

Reference yield:

(S)-2-(2,4,6-Trimethyl-phenyl)-[1,3]dioxolane-4-carboxylic acid methyl ester → (2R,4S)-4-{(Z)-(S)-5-[3-((S)-1-Hydroxy-propyl)-phenyl]-4-methyl-2-methylsulfanyl-pent-2-enyl}-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxolane-4-carboxylic acid methyl ester (594855-08-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium hexamethyldisilazide; HMPA / tetrahydrofuran

1.2: 53 percent / HMPA / tetrahydrofuran

2.1: tetrabutylammonium fluoride / tetrahydrofuran

3.1: benzene; methanol

With N,N,N,N,N,N-hexamethylphosphoric triamide; tetrabutyl ammonium fluoride; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; benzene;

DOI:10.1248/cpb.52.163

upstream raw materials:

diazomethyl-trimethyl-silane

mesytaldehyde

(S)-1-(3'-bromophenyl)-1-propanol

(S)-3-{3-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-propyl]-phenyl}-2-methyl-propionaldehyde

Downstream raw materials:

(2R,4S)-4-{(Z)-(S)-5-[3-((S)-1-Acetoxy-propyl)-phenyl]-4-methyl-2-methylsulfanyl-pent-2-enyl}-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxolane-4-carboxylic acid methyl ester

C₃₁H₃₈O₅S

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