(2S,5R,6R)-6-(tert-butyldimethylsilyloxy)-2,5-dihydroxyoctadecanyl 2',4',6'-triisopropylbenzenesulfonate

Base Information

Chemical Name:(2S,5R,6R)-6-(tert-butyldimethylsilyloxy)-2,5-dihydroxyoctadecanyl 2',4',6'-triisopropylbenzenesulfonate
CAS No.:460745-02-2
Molecular Formula:C₃₉H₇₄O₆SSi
Molecular Weight:699.164
Hs Code.:

Synonyms:(2S,5R,6R)-6-(tert-butyldimethylsilyloxy)-2,5-dihydroxyoctadecanyl 2',4',6'-triisopropylbenzenesulfonate

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Chemical Property of (2S,5R,6R)-6-(tert-butyldimethylsilyloxy)-2,5-dihydroxyoctadecanyl 2',4',6'-triisopropylbenzenesulfonate

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Technology Process of (2S,5R,6R)-6-(tert-butyldimethylsilyloxy)-2,5-dihydroxyoctadecanyl 2',4',6'-triisopropylbenzenesulfonate

There total 7 articles about (2S,5R,6R)-6-(tert-butyldimethylsilyloxy)-2,5-dihydroxyoctadecanyl 2',4',6'-triisopropylbenzenesulfonate 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: 87.0%

: 6553-96-4
2,4,6-triisopropylphenylsulfonyl chloride

: 460745-08-8
(2S,5R,6R)-6-(tert-butyldimethylsilyloxy)octadecane-1,2,5-triol

: 460745-02-2
(2S,5R,6R)-6-(tert-butyldimethylsilyloxy)-2,5-dihydroxyoctadecanyl 2',4',6'-triisopropylbenzenesulfonate

Guidance literature:: With pyridine; In dichloromethane; at 20 ℃; for 20h;
DOI:10.1021/ol026393j DOI:10.1002/chem.200305185

Reference yield:

: 929915-17-3
(4S)-4-[(3'R,4'R)-4'-(tert-butyldimethylsilyloxy)-3'-hydroxy-1'-hexadecynyl]-2-phenyl-1,3-dioxolane

: 460745-02-2
(2S,5R,6R)-6-(tert-butyldimethylsilyloxy)-2,5-dihydroxyoctadecanyl 2',4',6'-triisopropylbenzenesulfonate

Guidance literature:: Multi-step reaction with 2 steps

1: H₂ / Pd/C / ethyl acetate / 24 h / 20 °C

2: 87 percent / pyridine / CH₂Cl₂ / 20 h / 20 °C

With pyridine; hydrogen; palladium on activated charcoal; In dichloromethane; ethyl acetate;
DOI:10.1002/chem.200305185

Reference yield:

: 153062-86-3
(R)-tetradecane-1,2-diol

: 460745-02-2
(2S,5R,6R)-6-(tert-butyldimethylsilyloxy)-2,5-dihydroxyoctadecanyl 2',4',6'-triisopropylbenzenesulfonate

Guidance literature:: Multi-step reaction with 7 steps

1.1: pyridine / CH₂Cl₂ / 0 - 20 °C

2.1: imidazole / dimethylformamide / 0 - 20 °C

3.1: DIBAL-H / CH₂Cl₂ / -78 °C

4.1: Dess-Martin periodinane / CH₂Cl₂ / 20 °C

5.1: CSA / tetrahydrofuran / Heating

5.2: 96 percent / (1R,2S)-N-methylephedrine; Zn(OTf)2; Et₃N / toluene / 20 °C

6.1: 94 percent / H₂ / Pd/C / ethyl acetate / 24 h / 20 °C

7.1: 87 percent / pyridine / CH₂Cl₂ / 20 h / 20 °C

With pyridine; 1H-imidazole; camphor-10-sulfonic acid; hydrogen; diisobutylaluminium hydride; Dess-Martin periodane; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/ol026393j