(2R,5SR,6R,10R)-1-tert-butyldimethylsilyloxy-2,6,10-trimethyl-5-phenylsulfonyltridecane

Base Information

• Chemical Name: (2R,5SR,6R,10R)-1-tert-butyldimethylsilyloxy-2,6,10-trimethyl-5-phenylsulfonyltridecane
• CAS No.: 306739-98-0
• Molecular Formula: C₂₈H₅₂O₃SSi
• Molecular Weight: 496.871
• Mol file: 306739-98-0.mol

Synonyms:(2R,5SR,6R,10R)-1-tert-butyldimethylsilyloxy-2,6,10-trimethyl-5-phenylsulfonyltridecane

Chemical Property of (2R,5SR,6R,10R)-1-tert-butyldimethylsilyloxy-2,6,10-trimethyl-5-phenylsulfonyltridecane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,5SR,6R,10R)-1-tert-butyldimethylsilyloxy-2,6,10-trimethyl-5-phenylsulfonyltridecane

There total 11 articles about (2R,5SR,6R,10R)-1-tert-butyldimethylsilyloxy-2,6,10-trimethyl-5-phenylsulfonyltridecane 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: 96.0%

(2S)-(+)-(tert-Butyldimethyl)-(3-iodo-2-methylpropoxy)silane (147915-57-9) + (2R,6R)-2,6-dimethyl-1-phenylsulfonylnonane (306739-96-8) → (2R,5SR,6R,10R)-1-tert-butyldimethylsilyloxy-2,6,10-trimethyl-5-phenylsulfonyltridecane (306739-98-0)

Guidance literature:

(2R,6R)-2,6-dimethyl-1-phenylsulfonylnonane; With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; In tetrahydrofuran; hexane; at -78 - -30 ℃;

(2S)-(+)-(tert-Butyldimethyl)-(3-iodo-2-methylpropoxy)silane; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1271/bbb.64.1713

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (2R,5SR,6R,10R)-1-tert-butyldimethylsilyloxy-2,6,10-trimethyl-5-phenylsulfonyltridecane (306739-98-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 96 percent / imidazole / dimethylformamide / 3 h / 20 °C

2.1: 86 percent / (i-Bu)2AlH / CH₂Cl₂; hexane / 1 h / -78 °C

3.1: pyridine / 12 h / 0 °C

4.1: 2.45 g / NaI; NaHCO₃ / acetone / 3 h / Heating

5.1: HMPA; n-BuLi / tetrahydrofuran; hexane / -78 - -30 °C

5.2: 96 percent / tetrahydrofuran / -78 - 20 °C

With pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; diisobutylaluminium hydride; sodium hydrogencarbonate; sodium iodide; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; 1.1: Silylation / 2.1: Reduction / 3.1: Tosylation / 4.1: Iodination / 5.1: Deprotonation / 5.2: Alkylation;

DOI:10.1271/bbb.64.1713

Reference yield:

(3R)-4-(tert-butyldimethylsilanyloxy)-3-methylbutan-1-ol (147915-55-7) → (2R,5SR,6R,10R)-1-tert-butyldimethylsilyloxy-2,6,10-trimethyl-5-phenylsulfonyltridecane (306739-98-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: pyridine / 12 h / 0 °C

2.1: 2.45 g / NaI; NaHCO₃ / acetone / 3 h / Heating

3.1: HMPA; n-BuLi / tetrahydrofuran; hexane / -78 - -30 °C

3.2: 96 percent / tetrahydrofuran / -78 - 20 °C

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; sodium hydrogencarbonate; sodium iodide; In tetrahydrofuran; hexane; acetone; 1.1: Tosylation / 2.1: Iodination / 3.1: Deprotonation / 3.2: Alkylation;

DOI:10.1271/bbb.64.1713

upstream raw materials:

(2S)-(+)-(tert-Butyldimethyl)-(3-iodo-2-methylpropoxy)silane

(2R,6R)-2,6-dimethyl-1-phenylsulfonylnonane

tert-butyldimethylsilyl chloride

(3R)-4-(tert-butyldimethylsilanyloxy)-3-methylbutan-1-ol