(5R,6S,7S)-8-(4-methoxybenzyloxy)-1-(tert-butyldimethylsilyloxy)-6-hydroxy-5,7-dimethyloctan-4-one

Base Information

Chemical Name:(5R,6S,7S)-8-(4-methoxybenzyloxy)-1-(tert-butyldimethylsilyloxy)-6-hydroxy-5,7-dimethyloctan-4-one
CAS No.:945402-33-5
Molecular Formula:C₂₄H₄₂O₅Si
Molecular Weight:438.68
Hs Code.:

Synonyms:(5R,6S,7S)-8-(4-methoxybenzyloxy)-1-(tert-butyldimethylsilyloxy)-6-hydroxy-5,7-dimethyloctan-4-one

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Chemical Property of (5R,6S,7S)-8-(4-methoxybenzyloxy)-1-(tert-butyldimethylsilyloxy)-6-hydroxy-5,7-dimethyloctan-4-one

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Technology Process of (5R,6S,7S)-8-(4-methoxybenzyloxy)-1-(tert-butyldimethylsilyloxy)-6-hydroxy-5,7-dimethyloctan-4-one

There total 1 articles about (5R,6S,7S)-8-(4-methoxybenzyloxy)-1-(tert-butyldimethylsilyloxy)-6-hydroxy-5,7-dimethyloctan-4-one 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%

: 78878-05-4
1-iodo-3-(tert-butyldimethylsilyloxy)propane

: 252342-49-7
(2R,3S,4S)-3-hydroxy-5-(4-methoxybenzyloxy)-2,4-dimethylpentanoic acid methoxymethylamide

: 945402-33-5
(5R,6S,7S)-8-(4-methoxybenzyloxy)-1-(tert-butyldimethylsilyloxy)-6-hydroxy-5,7-dimethyloctan-4-one

Guidance literature:: 1-iodo-3-(tert-butyldimethylsilyloxy)propane; With tert.-butyl lithium; In diethyl ether; pentane; at -78 ℃; for 0.75h;

(2R,3S,4S)-3-hydroxy-5-(4-methoxybenzyloxy)-2,4-dimethylpentanoic acid methoxymethylamide; In diethyl ether; pentane; at -78 - -40 ℃; for 3.75h; Further stages.;
DOI:10.1021/jm061385k

Reference yield: 85.0%

: 945402-33-5
(5R,6S,7S)-8-(4-methoxybenzyloxy)-1-(tert-butyldimethylsilyloxy)-6-hydroxy-5,7-dimethyloctan-4-one

: 945402-09-5
(2S,3S,4S,5R)-1-(4-methoxybenzyloxy)-8-(tert-butyldimethylsilyloxy)-2,4-dimethyloctane-3,5-diol

Guidance literature:: (5R,6S,7S)-8-(4-methoxybenzyloxy)-1-(tert-butyldimethylsilyloxy)-6-hydroxy-5,7-dimethyloctan-4-one; With diethyl methoxy borane; In tetrahydrofuran; methanol; at -78 ℃; for 0.666667h;

With sodium tetrahydroborate; In tetrahydrofuran; methanol; at -78 ℃; for 7.16667h; Further stages.;
DOI:10.1021/jm061385k

Reference yield:

: 945402-33-5
(5R,6S,7S)-8-(4-methoxybenzyloxy)-1-(tert-butyldimethylsilyloxy)-6-hydroxy-5,7-dimethyloctan-4-one

: 945402-11-9
(2S,3S,4R,5R)-3-(4-methoxybenzyloxy)-5,8-bis(tert-butyldimethylsilyloxy)-2,4-dimethyloctan-1-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: Et₂BOMe / tetrahydrofuran; methanol / 0.67 h / -78 °C

1.2: 85 percent / NaBH₄ / tetrahydrofuran; methanol / 7.17 h / -78 °C

2.1: 60 percent / DDQ; molecular sieves 4 Angstroem / CH₂Cl₂ / 2 h / 0 - 20 °C

3.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / -78 - 0 °C

4.1: 41 percent / DIBALH / CH₂Cl₂; hexane / 12.5 h / -78 - -45 °C

With 2,6-dimethylpyridine; 4 A molecular sieve; diethyl methoxy borane; diisobutylaluminium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; hexane; dichloromethane;
DOI:10.1021/jm061385k