(2R,3R,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-8-[(4-methoxybenzyl)oxy]-3-(methoxymethoxy)-2-methyloctyl 4-methylbenzenesulfonate

Base Information

Chemical Name:(2R,3R,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-8-[(4-methoxybenzyl)oxy]-3-(methoxymethoxy)-2-methyloctyl 4-methylbenzenesulfonate
CAS No.:825612-56-4
Molecular Formula:C₃₂H₅₂O₈SSi
Molecular Weight:624.912
Hs Code.:

Synonyms:(2R,3R,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-8-[(4-methoxybenzyl)oxy]-3-(methoxymethoxy)-2-methyloctyl 4-methylbenzenesulfonate

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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 (2R,3R,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-8-[(4-methoxybenzyl)oxy]-3-(methoxymethoxy)-2-methyloctyl 4-methylbenzenesulfonate

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Technology Process of (2R,3R,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-8-[(4-methoxybenzyl)oxy]-3-(methoxymethoxy)-2-methyloctyl 4-methylbenzenesulfonate

There total 7 articles about (2R,3R,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-8-[(4-methoxybenzyl)oxy]-3-(methoxymethoxy)-2-methyloctyl 4-methylbenzenesulfonate 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: 100.0%

: 825612-55-3
(2R,3R,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-8-[(4-methoxybenzyl)oxy]-3-(methoxymethoxy)-2-methyl-1-octanol

: 98-59-9
p-toluenesulfonyl chloride

: 825612-56-4
(2R,3R,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-8-[(4-methoxybenzyl)oxy]-3-(methoxymethoxy)-2-methyloctyl 4-methylbenzenesulfonate

Guidance literature:: With pyridine; at 0 ℃; for 5h;
DOI:10.1002/chem.200400617

Reference yield:

: ethyl (3RS)-3-hydroxy-6-[(4-methoxybenzyl)oxy]hexanoate

: 825612-56-4
(2R,3R,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-8-[(4-methoxybenzyl)oxy]-3-(methoxymethoxy)-2-methyloctyl 4-methylbenzenesulfonate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0 - 23 °C

2.1: 83 percent / DIBAL / CH₂Cl₂ / 2 h / -78 °C

3.1: N,N,N',N'-tetramethyl-1,2-ethanediamine; TMEDA / TiCl₄ / CH₂Cl₂ / 0.33 h / 0 °C

3.2: 78 percent / CH₂Cl₂ / 1 h / 0 °C

4.1: 86 percent / N,N-diisopropylethylamine; Bu₄NI / CH₂Cl₂ / 12 h / 0 - 23 °C

5.1: 80 percent / aq. NaBH₄ / tetrahydrofuran / 12 h / 0 - 23 °C

6.1: 100 percent / pyridine / 5 h / 0 °C

With pyridine; 2,6-dimethylpyridine; sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; titanium tetrachloride; In tetrahydrofuran; dichloromethane;
DOI:10.1002/chem.200400617

Reference yield:

: 825612-52-0
(3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-6-[(4-methoxybenzyl)oxy]-hexanal

: 825612-56-4
(2R,3R,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-8-[(4-methoxybenzyl)oxy]-3-(methoxymethoxy)-2-methyloctyl 4-methylbenzenesulfonate

Guidance literature:: Multi-step reaction with 4 steps

1.1: N,N,N',N'-tetramethyl-1,2-ethanediamine; TMEDA / TiCl₄ / CH₂Cl₂ / 0.33 h / 0 °C

1.2: 78 percent / CH₂Cl₂ / 1 h / 0 °C

2.1: 86 percent / N,N-diisopropylethylamine; Bu₄NI / CH₂Cl₂ / 12 h / 0 - 23 °C

3.1: 80 percent / aq. NaBH₄ / tetrahydrofuran / 12 h / 0 - 23 °C

4.1: 100 percent / pyridine / 5 h / 0 °C

With pyridine; sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine; tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; titanium tetrachloride; In tetrahydrofuran; dichloromethane;
DOI:10.1002/chem.200400617