methyl (2R,3S,4S)-3-(tert-butyldimethylsilyloxy)-2,4-dimethyl-5-(4-methoxybenzyloxy)pentanoate

Base Information

Chemical Name:methyl (2R,3S,4S)-3-(tert-butyldimethylsilyloxy)-2,4-dimethyl-5-(4-methoxybenzyloxy)pentanoate
CAS No.:496035-37-1
Molecular Formula:C₂₂H₃₈O₅Si
Molecular Weight:410.626
Hs Code.:

Synonyms:methyl (2R,3S,4S)-3-(tert-butyldimethylsilyloxy)-2,4-dimethyl-5-(4-methoxybenzyloxy)pentanoate

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Chemical Property of methyl (2R,3S,4S)-3-(tert-butyldimethylsilyloxy)-2,4-dimethyl-5-(4-methoxybenzyloxy)pentanoate

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Technology Process of methyl (2R,3S,4S)-3-(tert-butyldimethylsilyloxy)-2,4-dimethyl-5-(4-methoxybenzyloxy)pentanoate

There total 9 articles about methyl (2R,3S,4S)-3-(tert-butyldimethylsilyloxy)-2,4-dimethyl-5-(4-methoxybenzyloxy)pentanoate 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: 99.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 496035-49-5
methyl (2R,3S,4S)-2,4-dimethyl-3-hydroxy-5-(4-methoxybenzyloxy)pentanoate

: 496035-37-1
methyl (2R,3S,4S)-3-(tert-butyldimethylsilyloxy)-2,4-dimethyl-5-(4-methoxybenzyloxy)pentanoate

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -78 - 20 ℃;
DOI:10.1021/jo048534w

Reference yield:

: 496035-35-9
(2S,4S)-1-hydroxy-5-(p-methoxybenzyloxy)-2,4-dimethylpentan-3-one

: 496035-37-1
methyl (2R,3S,4S)-3-(tert-butyldimethylsilyloxy)-2,4-dimethyl-5-(4-methoxybenzyloxy)pentanoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: dicyclohexylboron chloride; triethylamine / diethyl ether

1.2: LiBH₄ / diethyl ether

2.1: TEMPO; bis-acetoxyiodobenzene / CH₂Cl₂ / 3 h / 20 °C

3.1: sodium chlorite; 2-methyl-2-butene; NaH₂PO₄*2H₂O / 2-methyl-propan-2-ol; H₂O / 3 h / 20 °C

4.1: 226 mg / hexane; methanol

5.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / -78 - 20 °C

With 2,6-dimethylpyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; [bis(acetoxy)iodo]benzene; dicyclohexylboron chloride; triethylamine; In methanol; diethyl ether; hexane; dichloromethane; water; tert-butyl alcohol;
DOI:10.1021/jo048534w

Reference yield:

: 133007-95-1
(2S,3R,4S)-5-[(4-methoxybenzyl)oxy]-2,4-dimethylpentane-1,3-diol

: 496035-37-1
methyl (2R,3S,4S)-3-(tert-butyldimethylsilyloxy)-2,4-dimethyl-5-(4-methoxybenzyloxy)pentanoate

Guidance literature:: Multi-step reaction with 4 steps

1: TEMPO; bis-acetoxyiodobenzene / CH₂Cl₂ / 3 h / 20 °C

2: sodium chlorite; 2-methyl-2-butene; NaH₂PO₄*2H₂O / 2-methyl-propan-2-ol; H₂O / 3 h / 20 °C

3: 226 mg / hexane; methanol

4: 99 percent / 2,6-lutidine / CH₂Cl₂ / -78 - 20 °C

With 2,6-dimethylpyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; [bis(acetoxy)iodo]benzene; In methanol; hexane; dichloromethane; water; tert-butyl alcohol;
DOI:10.1021/jo048534w