(3S,5R,7S)-1,7-dibenzyloxy-9-(tert-butyldimethylsilyloxy)-8,8-dimethylnonane-3,5-diol

Base Information

Chemical Name:(3S,5R,7S)-1,7-dibenzyloxy-9-(tert-butyldimethylsilyloxy)-8,8-dimethylnonane-3,5-diol
CAS No.:470470-66-7
Molecular Formula:C₃₁H₅₀O₅Si
Molecular Weight:530.82
Hs Code.:

Synonyms:(3S,5R,7S)-1,7-dibenzyloxy-9-(tert-butyldimethylsilyloxy)-8,8-dimethylnonane-3,5-diol

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Chemical Property of (3S,5R,7S)-1,7-dibenzyloxy-9-(tert-butyldimethylsilyloxy)-8,8-dimethylnonane-3,5-diol

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Technology Process of (3S,5R,7S)-1,7-dibenzyloxy-9-(tert-butyldimethylsilyloxy)-8,8-dimethylnonane-3,5-diol

There total 10 articles about (3S,5R,7S)-1,7-dibenzyloxy-9-(tert-butyldimethylsilyloxy)-8,8-dimethylnonane-3,5-diol 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%

: 470470-65-6
(5S,7S)-1,7-dibenzyloxy-9-tert-butyldimethylsilyloxy-5-hydroxy-8,8-dimethylnonan-3-one

: 470470-66-7
(3S,5R,7S)-1,7-dibenzyloxy-9-(tert-butyldimethylsilyloxy)-8,8-dimethylnonane-3,5-diol

Guidance literature:: With tetramethylammonium triacetoxyborohydride; In acetic acid; acetonitrile; at -20 ℃; for 18h;
DOI:10.1016/S0040-4039(02)01054-7

Reference yield:

: 147252-93-5
(3S)-3-(benzyloxy)-2,2-dimethyl-4-penten-1-ol

: 470470-66-7
(3S,5R,7S)-1,7-dibenzyloxy-9-(tert-butyldimethylsilyloxy)-8,8-dimethylnonane-3,5-diol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 97 percent / imid.; DMAP; TBAI / 0.5 h / 20 °C

2.1: BH₃ / tetrahydrofuran / 18 h / -18 - 20 °C

2.2: 67 percent / NaOH; aq. H₂O₂ / 3 h / 50 °C

3.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.33 h / -78 °C

4.1: 49 percent / LDA / 0.03 h / -78 °C

5.1: 95 percent / Me₄NBH(OAc)3 / acetic acid; acetonitrile / 18 h / -20 °C

With 1H-imidazole; dmap; oxalyl dichloride; borane; tetra-(n-butyl)ammonium iodide; dimethyl sulfoxide; triethylamine; tetramethylammonium triacetoxyborohydride; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; acetic acid; acetonitrile;
DOI:10.1016/S0040-4039(02)01054-7

Reference yield:

: 470470-82-7
((S)-3-benzyloxy-2,2-dimethyl-pent-4-enyloxy)-tert-butyl-dimethyl-silane

: 470470-66-7
(3S,5R,7S)-1,7-dibenzyloxy-9-(tert-butyldimethylsilyloxy)-8,8-dimethylnonane-3,5-diol

Guidance literature:: Multi-step reaction with 4 steps

1.1: BH₃ / tetrahydrofuran / 18 h / -18 - 20 °C

1.2: 67 percent / NaOH; aq. H₂O₂ / 3 h / 50 °C

2.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.33 h / -78 °C

3.1: 49 percent / LDA / 0.03 h / -78 °C

4.1: 95 percent / Me₄NBH(OAc)3 / acetic acid; acetonitrile / 18 h / -20 °C

With oxalyl dichloride; borane; dimethyl sulfoxide; triethylamine; tetramethylammonium triacetoxyborohydride; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; acetic acid; acetonitrile;
DOI:10.1016/S0040-4039(02)01054-7