(2S,3S,4S,6R)-3-(4-methoxybenzyloxy)-7-(tert-butyldimethylsilyloxy)-2,4,6-trimethylheptyl acetate

Base Information

Chemical Name:(2S,3S,4S,6R)-3-(4-methoxybenzyloxy)-7-(tert-butyldimethylsilyloxy)-2,4,6-trimethylheptyl acetate
CAS No.:947380-82-7
Molecular Formula:C₂₆H₄₆O₅Si
Molecular Weight:466.734
Hs Code.:

Synonyms:(2S,3S,4S,6R)-3-(4-methoxybenzyloxy)-7-(tert-butyldimethylsilyloxy)-2,4,6-trimethylheptyl acetate

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Chemical Property of (2S,3S,4S,6R)-3-(4-methoxybenzyloxy)-7-(tert-butyldimethylsilyloxy)-2,4,6-trimethylheptyl acetate

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Technology Process of (2S,3S,4S,6R)-3-(4-methoxybenzyloxy)-7-(tert-butyldimethylsilyloxy)-2,4,6-trimethylheptyl acetate

There total 13 articles about (2S,3S,4S,6R)-3-(4-methoxybenzyloxy)-7-(tert-butyldimethylsilyloxy)-2,4,6-trimethylheptyl acetate 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: 95.0%

: 947380-81-6
(2S, 3S,4S,6R)-7-((tert-butyldimethylsilyl)oxy)-3-((4-methoxybenzyl)oxy)-2,4,6-trimethylheptan-1-ol

: 108-24-7
acetic anhydride

: 947380-82-7
(2S,3S,4S,6R)-3-(4-methoxybenzyloxy)-7-(tert-butyldimethylsilyloxy)-2,4,6-trimethylheptyl acetate

Guidance literature:: With pyridine; dmap; In dichloromethane; at 20 ℃;
DOI:10.1021/jo0704762

Reference yield:

: 881214-73-9
(2S,3S,4R,5S,6S)-5-(4-methoxybenzyloxy)-2,4,6-trimethylheptane-1,3,7-triol

: 947380-82-7
(2S,3S,4S,6R)-3-(4-methoxybenzyloxy)-7-(tert-butyldimethylsilyloxy)-2,4,6-trimethylheptyl acetate

Guidance literature:: Multi-step reaction with 12 steps

1.1: 90 percent / imidazole / CH₂Cl₂ / 0 °C

2.1: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

3.1: 93 percent / DIBALH / CH₂Cl₂ / -78 °C

4.1: 94 percent / DIEA; DMAP / CH₂Cl₂ / 0 - 20 °C

5.1: 95 percent / DDQ / CH₂Cl₂; H₂O / 0 °C

6.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

6.2: 100 percent / tetrahydrofuran / 0 - 20 °C

7.1: 91 percent / Bu₃SnH; AIBN / benzene / Heating

8.1: 90 percent / aq. HCl / tetrahydrofuran / 20 °C

9.1: 91 percent / CSA / CH₂Cl₂ / 5 h / 20 °C

10.1: 93 percent / imidazole / CH₂Cl₂ / 2 h / 20 °C

11.1: 92 percent / DIBAL-H / CH₂Cl₂ / -15 °C

12.1: 95 percent / pyridine; DMAP / CH₂Cl₂ / 20 °C

With pyridine; 1H-imidazole; hydrogenchloride; dmap; 2,2'-azobis(isobutyronitrile); camphor-10-sulfonic acid; tri-n-butyl-tin hydride; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; benzene; 2.1: Dess-Martin oxidation;
DOI:10.1021/jo0704762

Reference yield:

: 881214-71-7
(1R,4R,5R,6S,7R,8R)-7-(4-Methoxy-benzyloxy)-4,6,8-trimethyl-2,9-dioxa-bicyclo[3.3.1]nonan-3-one

: 947380-82-7
(2S,3S,4S,6R)-3-(4-methoxybenzyloxy)-7-(tert-butyldimethylsilyloxy)-2,4,6-trimethylheptyl acetate

Guidance literature:: Multi-step reaction with 13 steps

1.1: 93 percent / LiAlH₄ / tetrahydrofuran / 0 - 20 °C

2.1: 90 percent / imidazole / CH₂Cl₂ / 0 °C

3.1: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

4.1: 93 percent / DIBALH / CH₂Cl₂ / -78 °C

5.1: 94 percent / DIEA; DMAP / CH₂Cl₂ / 0 - 20 °C

6.1: 95 percent / DDQ / CH₂Cl₂; H₂O / 0 °C

7.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

7.2: 100 percent / tetrahydrofuran / 0 - 20 °C

8.1: 91 percent / Bu₃SnH; AIBN / benzene / Heating

9.1: 90 percent / aq. HCl / tetrahydrofuran / 20 °C

10.1: 91 percent / CSA / CH₂Cl₂ / 5 h / 20 °C

11.1: 93 percent / imidazole / CH₂Cl₂ / 2 h / 20 °C

12.1: 92 percent / DIBAL-H / CH₂Cl₂ / -15 °C

13.1: 95 percent / pyridine; DMAP / CH₂Cl₂ / 20 °C

With pyridine; 1H-imidazole; hydrogenchloride; dmap; lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); camphor-10-sulfonic acid; tri-n-butyl-tin hydride; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; benzene; 3.1: Dess-Martin oxidation;
DOI:10.1021/jo0704762