(4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-4,6-dimethylheptanoic acid

Base Information

Chemical Name:(4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-4,6-dimethylheptanoic acid
CAS No.:871236-54-3
Molecular Formula:C₂₃H₄₀O₅Si
Molecular Weight:424.653
Hs Code.:

Synonyms:(4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-4,6-dimethylheptanoic acid

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Chemical Property of (4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-4,6-dimethylheptanoic acid

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Technology Process of (4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-4,6-dimethylheptanoic acid

There total 6 articles about (4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-4,6-dimethylheptanoic acid 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:

: 871236-53-2
ethyl (4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-4,6-dimethylheptanoate

: 871236-54-3
(4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-4,6-dimethylheptanoic acid

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; at 60 ℃; for 6h;
DOI:10.1016/j.tet.2007.05.033

Reference yield:

: 792911-22-9
(-)-(2S,3R,4S)-3-((tert-butyldimethylsilyl)oxy)-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentan-1-ol

: 871236-54-3
(4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-4,6-dimethylheptanoic acid

Guidance literature:: Multi-step reaction with 4 steps

1.1: sulfur trioxide*pyridine complex; Et₃N; DMSO / CH₂Cl₂ / 20 °C

2.1: NaH / tetrahydrofuran / cooling

2.2: 8.96 g / tetrahydrofuran / cooling

3.1: 97 percent / NiCl₂*6H₂O; NaBH₄ / methanol; tetrahydrofuran / 0 °C

4.1: aq. LiOH / tetrahydrofuran / 6 h / 60 °C

With lithium hydroxide; sodium tetrahydroborate; sodium hydride; dimethyl sulfoxide; triethylamine; nickel dichloride; In tetrahydrofuran; methanol; dichloromethane; 2.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1016/j.tet.2007.05.033

Reference yield:

: 443761-65-7
(-)-(R)-4-benzyl-3-((2R,3S,4S)-3-((tert-butyldimethylsilyl)oxy)-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentanoyl)oxazolidin-2-one

: 871236-54-3
(4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-4,6-dimethylheptanoic acid

Guidance literature:: Multi-step reaction with 5 steps

1.1: 90 percent / LiBH₄ / methanol; tetrahydrofuran / 1.75 h / 0 - 20 °C

2.1: sulfur trioxide*pyridine complex; Et₃N; DMSO / CH₂Cl₂ / 20 °C

3.1: NaH / tetrahydrofuran / cooling

3.2: 8.96 g / tetrahydrofuran / cooling

4.1: 97 percent / NiCl₂*6H₂O; NaBH₄ / methanol; tetrahydrofuran / 0 °C

5.1: aq. LiOH / tetrahydrofuran / 6 h / 60 °C

With lithium hydroxide; sodium tetrahydroborate; lithium borohydride; sodium hydride; dimethyl sulfoxide; triethylamine; nickel dichloride; In tetrahydrofuran; methanol; dichloromethane; 3.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1016/j.tet.2007.05.033