(5S,6S,7S)-10-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3,3,5,7-tetramethyl-dec-1-en-4-ol

Base Information

Chemical Name:(5S,6S,7S)-10-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3,3,5,7-tetramethyl-dec-1-en-4-ol
CAS No.:871265-94-0
Molecular Formula:C₂₇H₄₈O₃Si
Molecular Weight:448.762
Hs Code.:

Synonyms:(5S,6S,7S)-10-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3,3,5,7-tetramethyl-dec-1-en-4-ol

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Chemical Property of (5S,6S,7S)-10-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3,3,5,7-tetramethyl-dec-1-en-4-ol

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Technology Process of (5S,6S,7S)-10-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3,3,5,7-tetramethyl-dec-1-en-4-ol

There total 8 articles about (5S,6S,7S)-10-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3,3,5,7-tetramethyl-dec-1-en-4-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: 94.0%

: 851955-73-2
(2R,3S,4S)-7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-heptanal

: C₅H₉ClMg

: 871265-94-0
(5S,6S,7S)-10-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3,3,5,7-tetramethyl-dec-1-en-4-ol

Guidance literature:: In tetrahydrofuran; at 20 ℃; for 1h;
DOI:10.1016/j.bioorg.2004.11.002

Reference yield:

: 851955-71-0
(2R,3S,4S)-7-Benzyloxy-3-hydroxy-2,4-dimethyl-heptanoic acid methoxy-methyl-amide

: 871265-94-0
(5S,6S,7S)-10-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3,3,5,7-tetramethyl-dec-1-en-4-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 96 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

2: 91 percent / DIBALH / tetrahydrofuran; toluene / 1 h / -78 - -50 °C

3: 94 percent / tetrahydrofuran / 1 h / 20 °C

With 2,6-dimethylpyridine; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1016/j.bioorg.2004.11.002

Reference yield:

: 851955-69-6
5-(benzyloxy)-N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylpentanamide

: 871265-94-0
(5S,6S,7S)-10-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3,3,5,7-tetramethyl-dec-1-en-4-ol

Guidance literature:: Multi-step reaction with 7 steps

1.1: 94 percent / LiCl; iPr₂NH; BuLi / tetrahydrofuran; hexane / 0.75 h / 0 °C

2.1: 75 percent / iPr₂NH; BuLi; BH₃*NH₃ / hexane; tetrahydrofuran / 16 h / 20 °C

3.1: 84 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 1.17 h / -78 - -30 °C

4.1: Bu₂B-OTf; Et₃N / CH₂Cl₂ / 2.5 h / -78 - 0 °C

4.2: 8 g / Me₃Al / tetrahydrofuran; hexane / 16 h / -5 - 20 °C

5.1: 96 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

6.1: 91 percent / DIBALH / tetrahydrofuran; toluene / 1 h / -78 - -50 °C

7.1: 94 percent / tetrahydrofuran / 1 h / 20 °C

With 2,6-dimethylpyridine; n-butyllithium; borane-ammonia complex; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; diisopropylamine; lithium chloride; In tetrahydrofuran; hexane; dichloromethane; toluene; 3.1: Swern oxidation;
DOI:10.1016/j.bioorg.2004.11.002