(4S)-4-[(3'R,4'R)-4'-(tert-butyldimethylsilyloxy)-3'-(p-toluenesulfonyloxy)octadecanyl]-2-phenyl-1,3-dioxolane

Base Information

Chemical Name:(4S)-4-[(3'R,4'R)-4'-(tert-butyldimethylsilyloxy)-3'-(p-toluenesulfonyloxy)octadecanyl]-2-phenyl-1,3-dioxolane
CAS No.:636596-54-8
Molecular Formula:C₃₈H₆₂O₆SSi
Molecular Weight:675.058
Hs Code.:

Synonyms:(4S)-4-[(3'R,4'R)-4'-(tert-butyldimethylsilyloxy)-3'-(p-toluenesulfonyloxy)octadecanyl]-2-phenyl-1,3-dioxolane

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (4S)-4-[(3'R,4'R)-4'-(tert-butyldimethylsilyloxy)-3'-(p-toluenesulfonyloxy)octadecanyl]-2-phenyl-1,3-dioxolane

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Technology Process of (4S)-4-[(3'R,4'R)-4'-(tert-butyldimethylsilyloxy)-3'-(p-toluenesulfonyloxy)octadecanyl]-2-phenyl-1,3-dioxolane

There total 8 articles about (4S)-4-[(3'R,4'R)-4'-(tert-butyldimethylsilyloxy)-3'-(p-toluenesulfonyloxy)octadecanyl]-2-phenyl-1,3-dioxolane 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%

: 98-59-9
p-toluenesulfonyl chloride

: 636596-53-7
(4S)-4-[(3'R,4'R)-4'-(tert-butyldimethylsilyloxy)-3'-hydroxyoctadecanyl]-2-phenyl-1,3-dioxolane

: 636596-54-8
(4S)-4-[(3'R,4'R)-4'-(tert-butyldimethylsilyloxy)-3'-(p-toluenesulfonyloxy)octadecanyl]-2-phenyl-1,3-dioxolane

Guidance literature:: With pyridine; at 20 ℃; for 7h;
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

: 636596-54-8
(4S)-4-[(3'R,4'R)-4'-(tert-butyldimethylsilyloxy)-3'-(p-toluenesulfonyloxy)octadecanyl]-2-phenyl-1,3-dioxolane

Guidance literature:: Multi-step reaction with 2 steps

1: 100 percent / H₂; Et₃N / Pd/C / ethyl acetate / 2.5 h / 20 °C

2: 96 percent / pyridine / 7 h / 20 °C

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

Reference yield:

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

: 636596-54-8
(4S)-4-[(3'R,4'R)-4'-(tert-butyldimethylsilyloxy)-3'-(p-toluenesulfonyloxy)octadecanyl]-2-phenyl-1,3-dioxolane

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: 100 percent / H₂; Et₃N / Pd/C / ethyl acetate / 2.5 h / 20 °C

7.1: 96 percent / pyridine / 7 h / 20 °C

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