(2S,3S,5S,6S,7R)-1-(tert-butyldimethylsilyloxy)-7-(4-methoxybenzyloxy)-2,6-dimethyloctane-3,5-diol

Base Information

Chemical Name:(2S,3S,5S,6S,7R)-1-(tert-butyldimethylsilyloxy)-7-(4-methoxybenzyloxy)-2,6-dimethyloctane-3,5-diol
CAS No.:1428738-00-4
Molecular Formula:C₂₄H₄₄O₅Si
Molecular Weight:440.696
Hs Code.:

Synonyms:(2S,3S,5S,6S,7R)-1-(tert-butyldimethylsilyloxy)-7-(4-methoxybenzyloxy)-2,6-dimethyloctane-3,5-diol

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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 (2S,3S,5S,6S,7R)-1-(tert-butyldimethylsilyloxy)-7-(4-methoxybenzyloxy)-2,6-dimethyloctane-3,5-diol

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Technology Process of (2S,3S,5S,6S,7R)-1-(tert-butyldimethylsilyloxy)-7-(4-methoxybenzyloxy)-2,6-dimethyloctane-3,5-diol

There total 9 articles about (2S,3S,5S,6S,7R)-1-(tert-butyldimethylsilyloxy)-7-(4-methoxybenzyloxy)-2,6-dimethyloctane-3,5-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: 91.0%

: 1428737-99-8
(2R,3R,6S,7S)-8-(tert-butyldimethylsilyloxy)-6-hydroxy-2-(4-methoxybenzyloxy)-3,7-dimethyloctan-4-one

: 1428738-00-4
(2S,3S,5S,6S,7R)-1-(tert-butyldimethylsilyloxy)-7-(4-methoxybenzyloxy)-2,6-dimethyloctane-3,5-diol

Guidance literature:: With tetramethylammonium triacetoxyborohydride; In acetic acid; acetonitrile; at -30 ℃; for 20h; stereoselective reaction;
DOI:10.1021/ol4004838

Reference yield:

: 1428737-97-6
(2R,3R)-N-methoxy-3-(4-methoxybenzyloxy)-N,2-dimethylbutanamide

: 1428738-00-4
(2S,3S,5S,6S,7R)-1-(tert-butyldimethylsilyloxy)-7-(4-methoxybenzyloxy)-2,6-dimethyloctane-3,5-diol

Guidance literature:: Multi-step reaction with 3 steps

1.1: tetrahydrofuran / 1.5 h / 0 - 55 °C

2.1: triethylamine; dicyclohexylboron chloride / hexane; diethyl ether / 1 h / -78 °C

2.2: 2 h / -78 °C

3.1: tetramethylammonium triacetoxyborohydride / acetonitrile; acetic acid / 20 h / -30 °C

With dicyclohexylboron chloride; triethylamine; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; diethyl ether; hexane; acetic acid; acetonitrile;
DOI:10.1021/ol4004838

Reference yield:

: 93454-85-4
(S)-3-(tert-butyldimethylsilyloxy)-2-methylpropionic acid methyl ester

: 1428738-00-4
(2S,3S,5S,6S,7R)-1-(tert-butyldimethylsilyloxy)-7-(4-methoxybenzyloxy)-2,6-dimethyloctane-3,5-diol

Guidance literature:: Multi-step reaction with 4 steps

1.1: isopropylmagnesium chloride / tetrahydrofuran / 1 h / -15 °C

2.1: diisobutylaluminium hydride / tetrahydrofuran; dichloromethane / 1.5 h / -78 °C

3.1: triethylamine; dicyclohexylboron chloride / hexane; diethyl ether / 1 h / -78 °C

3.2: 2 h / -78 °C

4.1: tetramethylammonium triacetoxyborohydride / acetonitrile; acetic acid / 20 h / -30 °C

With diisobutylaluminium hydride; dicyclohexylboron chloride; isopropylmagnesium chloride; triethylamine; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; acetic acid; acetonitrile;
DOI:10.1021/ol4004838