(2R,3R,4R)-1-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)-11-octadecyn-3,4-diol

Base Information

Chemical Name:(2R,3R,4R)-1-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)-11-octadecyn-3,4-diol
CAS No.:1215176-52-5
Molecular Formula:C₃₂H₅₆O₅Si
Molecular Weight:548.879
Hs Code.:

Synonyms:(2R,3R,4R)-1-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)-11-octadecyn-3,4-diol

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Chemical Property of (2R,3R,4R)-1-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)-11-octadecyn-3,4-diol

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Technology Process of (2R,3R,4R)-1-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)-11-octadecyn-3,4-diol

There total 12 articles about (2R,3R,4R)-1-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)-11-octadecyn-3,4-diol 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: 93.0%

: 1215176-47-8
(2R,3R,4R)-2-(4-methoxybenzyloxy)-11-octadecyn-1,3,4-triol

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1215176-52-5
(2R,3R,4R)-1-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)-11-octadecyn-3,4-diol

Guidance literature:: With dmap; In dichloromethane; at 20 ℃; for 3h;
DOI:10.1016/j.carres.2010.05.003

Reference yield:

: 824-94-2
p-methoxybenzyl chloride

: 1215176-52-5
(2R,3R,4R)-1-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)-11-octadecyn-3,4-diol

Guidance literature:: Multi-step reaction with 4 steps

1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3 h / 20 °C / Cooling with ice

2: diethyl ether; pentane; tetrahydrofuran / 16 h / -20 - 20 °C / Inert atmosphere

3: toluene-4-sulfonic acid / methanol / 2 h / 20 °C

4: dmap / dichloromethane / 3 h / 20 °C

With dmap; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; mineral oil; pentane;

Reference yield:

: 629-05-0
n-octyne

: 1215176-52-5
(2R,3R,4R)-1-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)-11-octadecyn-3,4-diol

Guidance literature:: Multi-step reaction with 8 steps

1.1: N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium / hexane; tetrahydrofuran / -40 °C

1.2: -40 - 20 °C

2.1: toluene-4-sulfonic acid / methanol / 6 h / 20 °C

3.1: triethylamine / dichloromethane / 0.5 h / 0 °C

4.1: sodium iodide / acetone / 16 h / Reflux

5.1: tert.-butyl lithium / diethyl ether; pentane / 1.08 h / -78 - 20 °C

5.2: 0.5 h / -40 - -30 °C / Inert atmosphere

6.1: diethyl ether; pentane; tetrahydrofuran / 16 h / -20 - 20 °C / Inert atmosphere

7.1: toluene-4-sulfonic acid / methanol / 2 h / 20 °C

8.1: dmap / dichloromethane / 3 h / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; n-butyllithium; tert.-butyl lithium; toluene-4-sulfonic acid; triethylamine; sodium iodide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; acetone; pentane;