Silane, (1,1-dimethylethyl)[(1S)-1-[3-[(2S,3Z)-5-iodo-2-methyl-4-(methylthio)-3- pentenyl]phenyl]propoxy]dimethyl-

Base Information

• Chemical Name: Silane, (1,1-dimethylethyl)[(1S)-1-[3-[(2S,3Z)-5-iodo-2-methyl-4-(methylthio)-3- pentenyl]phenyl]propoxy]dimethyl-
• CAS No.: 594855-06-8
• Molecular Formula: C22H37IOSSi
• Molecular Weight: 504.591

Synonyms:

Chemical Property of Silane, (1,1-dimethylethyl)[(1S)-1-[3-[(2S,3Z)-5-iodo-2-methyl-4-(methylthio)-3- pentenyl]phenyl]propoxy]dimethyl-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Silane, (1,1-dimethylethyl)[(1S)-1-[3-[(2S,3Z)-5-iodo-2-methyl-4-(methylthio)-3- pentenyl]phenyl]propoxy]dimethyl-

There total 11 articles about Silane, (1,1-dimethylethyl)[(1S)-1-[3-[(2S,3Z)-5-iodo-2-methyl-4-(methylthio)-3- pentenyl]phenyl]propoxy]dimethyl- 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: 100.0%

(Z)-(S)-5-{3-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-propyl]-phenyl}-4-methyl-2-methylsulfanyl-pent-2-en-1-ol (594855-05-7) → tert-Butyl-{(S)-1-[3-((Z)-(S)-5-iodo-2-methyl-4-methylsulfanyl-pent-3-enyl)-phenyl]-propoxy}-dimethyl-silane (594855-06-8)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In diethyl ether; acetonitrile;

DOI:10.1248/cpb.52.163

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → tert-Butyl-{(S)-1-[3-((Z)-(S)-5-iodo-2-methyl-4-methylsulfanyl-pent-3-enyl)-phenyl]-propoxy}-dimethyl-silane (594855-06-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 61 percent / imidazole / dimethylformamide

2.1: 92 percent / NaBH₄ / ethanol

3.1: 95 percent / NaH / tetrahydrofuran

4.1: 94 percent / n-Bu₃SnH / toluene

5.1: 70 percent / aq. p-TsOH / ethanol

6.1: 96 percent / (COCl)2; DMSO; TEA / CH₂Cl₂

7.1: lithium hexamethyldisilazide / tetrahydrofuran

7.2: 88 percent / tetrahydrofuran

8.1: 78 percent / MsCl; TEA; DBU / CH₂Cl₂; tetrahydrofuran

9.1: 82 percent / DIBAL-H / CH₂Cl₂

10.1: 100 percent / I₂; Ph₃P; imidazole / diethyl ether; acetonitrile

With 1H-imidazole; sodium tetrahydroborate; oxalyl dichloride; TEA; 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; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 6.1: Swern oxidation;

DOI:10.1248/cpb.52.163

Reference yield:

(S)-1-(3'-bromophenyl)-1-propanol (224622-38-2) → tert-Butyl-{(S)-1-[3-((Z)-(S)-5-iodo-2-methyl-4-methylsulfanyl-pent-3-enyl)-phenyl]-propoxy}-dimethyl-silane (594855-06-8)

Guidance literature:

Multi-step reaction with 11 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

With 1H-imidazole; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; TEA; 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; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 7.1: Swern oxidation;

DOI:10.1248/cpb.52.163

upstream raw materials:

(Z)-(S)-5-{3-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-propyl]-phenyl}-4-methyl-2-methylsulfanyl-pent-2-en-1-ol

tert-butyldimethylsilyl chloride

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

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

Downstream raw materials:

C₃₁H₃₈O₅S

(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

(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

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

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