(2R,5RS,6R,10R)-2-tertbutyldimethylsilyloxy-6,10,14-trimethyl-5-phenylsulfonylpentadecane

Base Information

• Chemical Name: (2R,5RS,6R,10R)-2-tertbutyldimethylsilyloxy-6,10,14-trimethyl-5-phenylsulfonylpentadecane
• CAS No.: 306739-81-1
• Molecular Formula: C₃₀H₅₆O₃SSi
• Molecular Weight: 524.924
• Mol file: 306739-81-1.mol

Synonyms:(2R,5RS,6R,10R)-2-tertbutyldimethylsilyloxy-6,10,14-trimethyl-5-phenylsulfonylpentadecane

Chemical Property of (2R,5RS,6R,10R)-2-tertbutyldimethylsilyloxy-6,10,14-trimethyl-5-phenylsulfonylpentadecane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,5RS,6R,10R)-2-tertbutyldimethylsilyloxy-6,10,14-trimethyl-5-phenylsulfonylpentadecane

There total 8 articles about (2R,5RS,6R,10R)-2-tertbutyldimethylsilyloxy-6,10,14-trimethyl-5-phenylsulfonylpentadecane 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: 84.0%

(2R,6R)-2,6,10-trimethyl-1-(phenylsulfonyl)undecane (131636-82-3) + (R)-3-((tert-butyldimethylsilyl)oxy)-1-iodobutane (109613-36-7) → (2R,5RS,6R,10R)-2-tertbutyldimethylsilyloxy-6,10,14-trimethyl-5-phenylsulfonylpentadecane (306739-81-1)

Guidance literature:

(2R,6R)-2,6,10-trimethyl-1-(phenylsulfonyl)undecane; With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; In tetrahydrofuran; hexane; at -78 - -30 ℃;

(R)-3-((tert-butyldimethylsilyl)oxy)-1-iodobutane; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1271/bbb.64.1713

Reference yield:

(2R,6R)-2,6,10-trimethyl-undecan-1-ol (54154-25-5) → (2R,5RS,6R,10R)-2-tertbutyldimethylsilyloxy-6,10,14-trimethyl-5-phenylsulfonylpentadecane (306739-81-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 1.37 g / pyridine / 10 h / 0 °C

2.1: 1.04 g / NaI / acetone / 4 h / Heating

3.1: 89 percent / dimethylformamide / 12 h / 20 °C

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

4.2: 84 percent / tetrahydrofuran / -78 - 20 °C

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; sodium iodide; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; acetone; 1.1: Tosylation / 2.1: Iodination / 3.1: Substitution / 4.1: Deprotonation / 4.2: Alkylation;

DOI:10.1271/bbb.64.1713

Reference yield:

(3-methylbutyl)magnesium bromide (4548-78-1) → (2R,5RS,6R,10R)-2-tertbutyldimethylsilyloxy-6,10,14-trimethyl-5-phenylsulfonylpentadecane (306739-81-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 91 percent / Li₂CuCl₄ / tetrahydrofuran / -78 - 0 °C

2.1: 94 percent / (n-Bu)4NF / tetrahydrofuran / 4 h / 20 °C

3.1: 1.37 g / pyridine / 10 h / 0 °C

4.1: 1.04 g / NaI / acetone / 4 h / Heating

5.1: 89 percent / dimethylformamide / 12 h / 20 °C

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

6.2: 84 percent / tetrahydrofuran / -78 - 20 °C

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; dilithium tetrachlorocuprate; tetrabutyl ammonium fluoride; sodium iodide; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; acetone; 1.1: Addition / 2.1: Hydrolysis / 3.1: Tosylation / 4.1: Iodination / 5.1: Substitution / 6.1: Deprotonation / 6.2: Alkylation;

DOI:10.1271/bbb.64.1713

upstream raw materials:

(2R,6R)-2,6,10-trimethyl-1-(phenylsulfonyl)undecane

(R)-3-((tert-butyldimethylsilyl)oxy)-1-iodobutane

(2R,6R)-2,6,10-trimethyl-undecan-1-ol

sodium benzenesulfonate