(2S,3S,4R)-1,4-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-methyl-pentan-2-ol

Base Information

Chemical Name:(2S,3S,4R)-1,4-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-methyl-pentan-2-ol
CAS No.:398516-94-4
Molecular Formula:C₂₆H₄₀O₄Si
Molecular Weight:444.687
Hs Code.:

Synonyms:(2S,3S,4R)-1,4-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-methyl-pentan-2-ol

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Chemical Property of (2S,3S,4R)-1,4-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-methyl-pentan-2-ol

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Technology Process of (2S,3S,4R)-1,4-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-methyl-pentan-2-ol

There total 11 articles about (2S,3S,4R)-1,4-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-methyl-pentan-2-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: 96.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 632357-79-0
(2R,3S,4S)-2,5-Bis-benzyloxy-3-methyl-pentane-1,4-diol

: 398516-94-4
(2S,3S,4R)-1,4-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-methyl-pentan-2-ol

Guidance literature:: With 1H-imidazole; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1021/jo034930n

Reference yield:

: 398516-92-2
(4S,5S)-6-Benzyloxy-5-hydroxy-4-methyl-hex-1-en-3-one

: 398516-94-4
(2S,3S,4R)-1,4-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-methyl-pentan-2-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: Et₃B / tetrahydrofuran; methanol; hexane / 1 h / -78 °C

1.2: 95 percent / NaBH₄ / tetrahydrofuran; methanol; hexane / 1 h / -78 °C

2.1: CSA / CH₂Cl₂ / 1 h / 20 °C

3.1: 85 percent / DIBAL / CH₂Cl₂; hexane / 1 h / 20 °C

4.1: OsO₄; N-methylmorpholine N-oxide / acetone; H₂O / 16 h / 20 °C

4.2: NaIO₄ / acetone; H₂O / 0.02 h / 20 °C

4.3: 91 percent / NaBH₄ / ethanol / 0.5 h / 0 °C

5.1: 96 percent / imidazole / CH₂Cl₂ / 1 h / 0 °C

With 1H-imidazole; osmium(VIII) oxide; triethyl borane; camphor-10-sulfonic acid; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; methanol; hexane; dichloromethane; water; acetone;
DOI:10.1021/jo034930n

Reference yield:

: 632357-78-9
(2S,3R,4S)-1-Benzyloxy-3-methyl-hex-5-ene-2,4-diol

: 398516-94-4
(2S,3S,4R)-1,4-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-methyl-pentan-2-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: CSA / CH₂Cl₂ / 1 h / 20 °C

2.1: 85 percent / DIBAL / CH₂Cl₂; hexane / 1 h / 20 °C

3.1: OsO₄; N-methylmorpholine N-oxide / acetone; H₂O / 16 h / 20 °C

3.2: NaIO₄ / acetone; H₂O / 0.02 h / 20 °C

3.3: 91 percent / NaBH₄ / ethanol / 0.5 h / 0 °C

4.1: 96 percent / imidazole / CH₂Cl₂ / 1 h / 0 °C

With 1H-imidazole; osmium(VIII) oxide; camphor-10-sulfonic acid; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; In hexane; dichloromethane; water; acetone;
DOI:10.1021/jo034930n