(2R,3S,4S,5S)-5-Benzyloxymethoxy-1-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2,4-dimethyl-heptan-3-ol

Base Information

Chemical Name:(2R,3S,4S,5S)-5-Benzyloxymethoxy-1-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2,4-dimethyl-heptan-3-ol
CAS No.:482626-36-8
Molecular Formula:C₃₁H₅₀O₆Si
Molecular Weight:546.82
Hs Code.:

Synonyms:(2R,3S,4S,5S)-5-Benzyloxymethoxy-1-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2,4-dimethyl-heptan-3-ol

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Chemical Property of (2R,3S,4S,5S)-5-Benzyloxymethoxy-1-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2,4-dimethyl-heptan-3-ol

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Technology Process of (2R,3S,4S,5S)-5-Benzyloxymethoxy-1-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2,4-dimethyl-heptan-3-ol

There total 7 articles about (2R,3S,4S,5S)-5-Benzyloxymethoxy-1-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2,4-dimethyl-heptan-3-ol 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%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 482626-35-7
(2R,3S,4S,5S)-5-Benzyloxymethoxy-7-(4-methoxy-benzyloxy)-2,4-dimethyl-heptane-1,3-diol

: 482626-36-8
(2R,3S,4S,5S)-5-Benzyloxymethoxy-1-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2,4-dimethyl-heptan-3-ol

Guidance literature:: With 1H-imidazole; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1021/ja0279646

Reference yield:

: 152330-77-3
(2R,3S)-3-hydroxy-N-methoxy-5-(4-methoxybenzyloxy)-N,2-dimethylpentanamide

: 482626-36-8
(2R,3S,4S,5S)-5-Benzyloxymethoxy-1-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2,4-dimethyl-heptan-3-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: DIPEA; TBAI / CH₂Cl₂ / 15 h / 20 °C

2.1: DIBAL / tetrahydrofuran / 1 h / -78 °C

3.1: n-Bu₂BOTf; TEA / CH₂Cl₂ / 0.5 h / -40 - 0 °C

3.2: CH₂Cl₂ / 5 h / -78 - 0 °C

4.1: aq. NaBH₄ / tetrahydrofuran / 3 h / 20 °C

5.1: imidazole / CH₂Cl₂ / 1 h / 0 °C

With 1H-imidazole; sodium tetrahydroborate; di-n-butylboryl trifluoromethanesulfonate; TEA; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja016272z

Reference yield:

: 128461-65-4
3-(p-methoxybenzyloxy)propanal

: 482626-36-8
(2R,3S,4S,5S)-5-Benzyloxymethoxy-1-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2,4-dimethyl-heptan-3-ol

Guidance literature:: Multi-step reaction with 7 steps

1.1: n-Bu₂BOTf; TEA / CH₂Cl₂ / 0.5 h / -40 - 0 °C

1.2: CH₂Cl₂ / 5 h / -78 - 0 °C

2.1: Me₃Al / tetrahydrofuran / 3 h / -20 - 20 °C

3.1: DIPEA; TBAI / CH₂Cl₂ / 15 h / 20 °C

4.1: DIBAL / tetrahydrofuran / 1 h / -78 °C

5.1: n-Bu₂BOTf; TEA / CH₂Cl₂ / 0.5 h / -40 - 0 °C

5.2: CH₂Cl₂ / 5 h / -78 - 0 °C

6.1: aq. NaBH₄ / tetrahydrofuran / 3 h / 20 °C

7.1: imidazole / CH₂Cl₂ / 1 h / 0 °C

With 1H-imidazole; sodium tetrahydroborate; di-n-butylboryl trifluoromethanesulfonate; TEA; trimethylaluminum; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja016272z