(2R,4RS,6R)-1-tert-butyldimethylsilyloxy-2,6-dimethyl-4-phenylsulfonyl-7-tetrahydropyranyloxyheptane

Base Information

• Chemical Name: (2R,4RS,6R)-1-tert-butyldimethylsilyloxy-2,6-dimethyl-4-phenylsulfonyl-7-tetrahydropyranyloxyheptane
• CAS No.: 299430-21-0
• Molecular Formula: C₂₆H₄₆O₅SSi
• Molecular Weight: 498.8
• Mol file: 299430-21-0.mol

Synonyms:(2R,4RS,6R)-1-tert-butyldimethylsilyloxy-2,6-dimethyl-4-phenylsulfonyl-7-tetrahydropyranyloxyheptane

Chemical Property of (2R,4RS,6R)-1-tert-butyldimethylsilyloxy-2,6-dimethyl-4-phenylsulfonyl-7-tetrahydropyranyloxyheptane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4RS,6R)-1-tert-butyldimethylsilyloxy-2,6-dimethyl-4-phenylsulfonyl-7-tetrahydropyranyloxyheptane

There total 7 articles about (2R,4RS,6R)-1-tert-butyldimethylsilyloxy-2,6-dimethyl-4-phenylsulfonyl-7-tetrahydropyranyloxyheptane 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: 91.0%

(2S)-(+)-(tert-butyl-dimethyl)-(3-iodo-2-methyl-propoxy)-silane (168335-78-2) + (R)-2-methyl-4-phenylsulfonyl-1-tetrahydropyranyloxybutane (299430-20-9) → (2R,4RS,6R)-1-tert-butyldimethylsilyloxy-2,6-dimethyl-4-phenylsulfonyl-7-tetrahydropyranyloxyheptane (299430-21-0)

Guidance literature:

(R)-2-methyl-4-phenylsulfonyl-1-tetrahydropyranyloxybutane; With n-butyllithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; at -30 ℃; for 1h;

(2S)-(+)-(tert-butyl-dimethyl)-(3-iodo-2-methyl-propoxy)-silane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; at 20 ℃; for 10h;

DOI:10.1002/1099-0690(200008)2000:15<2745::AID-EJOC2745>3.0.CO;2-I

Reference yield:

sodium benzenesulfonate (873-55-2) → (2R,4RS,6R)-1-tert-butyldimethylsilyloxy-2,6-dimethyl-4-phenylsulfonyl-7-tetrahydropyranyloxyheptane (299430-21-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 85 percent / dimethylformamide / 12 h / 20 °C

2.1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 1 h / -30 °C

2.2: 91 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 10 h / 20 °C

With n-butyllithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; N,N-dimethyl-formamide; 1.1: Alkylation / 2.1: Metallation / 2.2: Alkylation;

DOI:10.1002/1099-0690(200008)2000:15<2745::AID-EJOC2745>3.0.CO;2-I

Reference yield:

(R)-3-(tert-butyldimethylsilyloxy)-2-methylpropan-1-ol (112057-64-4) → (2R,4RS,6R)-1-tert-butyldimethylsilyloxy-2,6-dimethyl-4-phenylsulfonyl-7-tetrahydropyranyloxyheptane (299430-21-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 100 percent / pyridine / 12 h / 0 °C

2.1: 92 percent / NaI; NaHCO₃ / acetone / 4 h / Heating

3.1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 1 h / -30 °C

3.2: 91 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 10 h / 20 °C

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

DOI:10.1002/1099-0690(200008)2000:15<2745::AID-EJOC2745>3.0.CO;2-I

upstream raw materials:

(2S)-(+)-(tert-butyl-dimethyl)-(3-iodo-2-methyl-propoxy)-silane

(R)-2-methyl-4-phenylsulfonyl-1-tetrahydropyranyloxybutane

sodium benzenesulfonate

(R)-3-(tert-butyldimethylsilyloxy)-2-methylpropan-1-ol

Downstream raw materials:

(2S,6R)-2,6-dimethylpentadecyl tosylate

(2R,6S)-2,6-dimethylpentadecyl tosylate

(2R,6S)-2,6-dimethyltetradecyl tosylate

(2R,6R)-2,6-dimethyl-7-tetrahydropyranyloxyheptyl p-toleuenesulfonate