(2R,4S,5S)-2-tert-butyldimethylsilyloxy-5-hydroxy-4-hydroxymethyl-1-(4-methoxy)benzyloxy-7-methyloctane

Base Information

Chemical Name:(2R,4S,5S)-2-tert-butyldimethylsilyloxy-5-hydroxy-4-hydroxymethyl-1-(4-methoxy)benzyloxy-7-methyloctane
CAS No.:866138-93-4
Molecular Formula:C₂₄H₄₄O₅Si
Molecular Weight:440.696
Hs Code.:

Synonyms:(2R,4S,5S)-2-tert-butyldimethylsilyloxy-5-hydroxy-4-hydroxymethyl-1-(4-methoxy)benzyloxy-7-methyloctane

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Chemical Property of (2R,4S,5S)-2-tert-butyldimethylsilyloxy-5-hydroxy-4-hydroxymethyl-1-(4-methoxy)benzyloxy-7-methyloctane

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Technology Process of (2R,4S,5S)-2-tert-butyldimethylsilyloxy-5-hydroxy-4-hydroxymethyl-1-(4-methoxy)benzyloxy-7-methyloctane

There total 9 articles about (2R,4S,5S)-2-tert-butyldimethylsilyloxy-5-hydroxy-4-hydroxymethyl-1-(4-methoxy)benzyloxy-7-methyloctane 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: 94.0%

: 866138-83-2
(R)-4-benzyl-3-((2R,3S)-2-((R)-2-(tert-butyldimethylsilyloxy)-3-(4-methoxybenzyloxy)propyl)-3-hydroxy-5-methylhexanoyl)oxazolidin-2-one

: 866138-93-4
(2R,4S,5S)-2-tert-butyldimethylsilyloxy-5-hydroxy-4-hydroxymethyl-1-(4-methoxy)benzyloxy-7-methyloctane

Guidance literature:: With lithium borohydride; In tetrahydrofuran; methanol; at 0 - 20 ℃;
DOI:10.1021/ol051200o

Reference yield:

: (R)-4-hydroxy-5-(4-methoxybenzyloxy)pentanoic acid

: 866138-93-4
(2R,4S,5S)-2-tert-butyldimethylsilyloxy-5-hydroxy-4-hydroxymethyl-1-(4-methoxy)benzyloxy-7-methyloctane

Guidance literature:: Multi-step reaction with 6 steps

1: imidazole / CH₂Cl₂ / 5 h / 20 °C

2: 6.6 g / aq. K₂CO₃ / methanol; tetrahydrofuran / 1 h / 0 °C

3: Et₃N / tetrahydrofuran / 3 h / 0 °C

4: 6.7 g / BuLi / tetrahydrofuran; hexane / 2 h / -78 °C

5: 72 percent / TiCl₄; (i-Pr)2NEt / CH₂Cl₂ / 4 h / -78 - 0 °C

6: 94 percent / LiBH₄ / methanol; tetrahydrofuran / 0 - 20 °C

With 1H-imidazole; lithium borohydride; n-butyllithium; titanium tetrachloride; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; hexane; dichloromethane;
DOI:10.1021/ol051200o

Reference yield:

: 866138-76-3
(R)-4-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)pentanoic acid

: 866138-93-4
(2R,4S,5S)-2-tert-butyldimethylsilyloxy-5-hydroxy-4-hydroxymethyl-1-(4-methoxy)benzyloxy-7-methyloctane

Guidance literature:: Multi-step reaction with 4 steps

1: Et₃N / tetrahydrofuran / 3 h / 0 °C

2: 6.7 g / BuLi / tetrahydrofuran; hexane / 2 h / -78 °C

3: 72 percent / TiCl₄; (i-Pr)2NEt / CH₂Cl₂ / 4 h / -78 - 0 °C

4: 94 percent / LiBH₄ / methanol; tetrahydrofuran / 0 - 20 °C

With lithium borohydride; n-butyllithium; titanium tetrachloride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; hexane; dichloromethane;
DOI:10.1021/ol051200o