(2S,3S,4R,5S)-5-(tert-butyldimethylsilanyloxy)-3-hydroxy-6-(4-methoxybenzyloxy)-2,4-dimethylhexanoic acid methoxy-methyl-amide

Base Information

Chemical Name:(2S,3S,4R,5S)-5-(tert-butyldimethylsilanyloxy)-3-hydroxy-6-(4-methoxybenzyloxy)-2,4-dimethylhexanoic acid methoxy-methyl-amide
CAS No.:475232-99-6
Molecular Formula:C₂₄H₄₃NO₆Si
Molecular Weight:469.694
Hs Code.:

Synonyms:(2S,3S,4R,5S)-5-(tert-butyldimethylsilanyloxy)-3-hydroxy-6-(4-methoxybenzyloxy)-2,4-dimethylhexanoic acid methoxy-methyl-amide

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Chemical Property of (2S,3S,4R,5S)-5-(tert-butyldimethylsilanyloxy)-3-hydroxy-6-(4-methoxybenzyloxy)-2,4-dimethylhexanoic acid methoxy-methyl-amide

Chemical Property:

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Technology Process of (2S,3S,4R,5S)-5-(tert-butyldimethylsilanyloxy)-3-hydroxy-6-(4-methoxybenzyloxy)-2,4-dimethylhexanoic acid methoxy-methyl-amide

There total 1 articles about (2S,3S,4R,5S)-5-(tert-butyldimethylsilanyloxy)-3-hydroxy-6-(4-methoxybenzyloxy)-2,4-dimethylhexanoic acid methoxy-methyl-amide 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:

: 69739-34-0
t-butyldimethylsiyl triflate

: (S)-5-Hydroxy-6-(4-methoxy-benzyloxy)-2,4-dimethyl-3-oxo-hexanoic acid methoxy-methyl-amide

: (2S,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-2,4-dimethyl-3-oxo-hexanoic acid methoxy-methyl-amide

: 475232-99-6
(2S,3S,4R,5S)-5-(tert-butyldimethylsilanyloxy)-3-hydroxy-6-(4-methoxybenzyloxy)-2,4-dimethylhexanoic acid methoxy-methyl-amide

Guidance literature:: t-butyldimethylsiyl triflate; (S)-5-Hydroxy-6-(4-methoxy-benzyloxy)-2,4-dimethyl-3-oxo-hexanoic acid methoxy-methyl-amide; With 2,6-dimethylpyridine; In dichloromethane; at -78 ℃; for 0.5h;

With potassium triethylborohydride; In diethyl ether; at -78 ℃; for 0.5h;
DOI:10.1016/S0040-4020(02)00723-8

Reference yield: 74.0%

: 3587-60-8
Benzyloxymethyl chloride

: 475232-99-6
(2S,3S,4R,5S)-5-(tert-butyldimethylsilanyloxy)-3-hydroxy-6-(4-methoxybenzyloxy)-2,4-dimethylhexanoic acid methoxy-methyl-amide

: 475233-00-2
(2S,3S,4R,5S)-3-benzyloxymethoxy-5-(tert-butyldimethylsilanyloxy)-6-(4-methoxybenzyloxy)-2,4-dimethylhexanoic acid methoxy-methyl-amide

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 192h;
DOI:10.1016/S0040-4020(02)00723-8

Reference yield:

: 475232-99-6
(2S,3S,4R,5S)-5-(tert-butyldimethylsilanyloxy)-3-hydroxy-6-(4-methoxybenzyloxy)-2,4-dimethylhexanoic acid methoxy-methyl-amide

: 475233-02-4
(3R,4R,5R,6S)-4-benzyloxymethoxy-6-(tert-butyldimethylsilanyloxy)-4-(4-methoxybenzyloxy)-3,5-dimethylheptan-1-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 74 percent / i-Pr₂NEt / CH₂Cl₂ / 192 h / 20 °C

2.1: DIBAL-H / tetrahydrofuran / 0.5 h / -78 °C

3.1: NaHMDS / tetrahydrofuran; diethyl ether / 4 h / 0 °C

3.2: 0.106 g / diethyl ether; tetrahydrofuran / 0.42 h / 0 °C

4.1: 9-BBN / tetrahydrofuran / 7 h / 20 °C

4.2: 98 percent / aq. NaOH; H₂O₂ / tetrahydrofuran / 1 h / 0 °C

With 9-borabicyclo[3.3.1]nonane dimer; sodium hexamethyldisilazane; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; 3.2: Wittig reaction;
DOI:10.1016/S0040-4020(02)00723-8