(3R,5S)-1-(tert-Butyl-diphenyl-silanyloxy)-6-[1,3]dithian-2-yl-6-methyl-heptane-3,5-diol

Base Information

Chemical Name:(3R,5S)-1-(tert-Butyl-diphenyl-silanyloxy)-6-[1,3]dithian-2-yl-6-methyl-heptane-3,5-diol
CAS No.:913722-28-8
Molecular Formula:C₂₈H₄₂O₃S₂Si
Molecular Weight:518.857
Hs Code.:

Synonyms:(3R,5S)-1-(tert-Butyl-diphenyl-silanyloxy)-6-[1,3]dithian-2-yl-6-methyl-heptane-3,5-diol

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Chemical Property of (3R,5S)-1-(tert-Butyl-diphenyl-silanyloxy)-6-[1,3]dithian-2-yl-6-methyl-heptane-3,5-diol

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Technology Process of (3R,5S)-1-(tert-Butyl-diphenyl-silanyloxy)-6-[1,3]dithian-2-yl-6-methyl-heptane-3,5-diol

There total 12 articles about (3R,5S)-1-(tert-Butyl-diphenyl-silanyloxy)-6-[1,3]dithian-2-yl-6-methyl-heptane-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: 58.0%

: 913722-27-7
(3R,5S)-6-[1,3]Dithian-2-yl-6-methyl-heptane-1,3,5-triol

: 58479-61-1
tert-butylchlorodiphenylsilane

: 913722-28-8
(3R,5S)-1-(tert-Butyl-diphenyl-silanyloxy)-6-[1,3]dithian-2-yl-6-methyl-heptane-3,5-diol

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h;
DOI:10.1021/ol061626i

Reference yield:

: 913722-16-4
(2S,5R,6R)-5-Hydroxy-6-hydroxymethyl-2-methoxy-3,3-dimethyl-tetrahydro-pyran-4-one

: 913722-28-8
(3R,5S)-1-(tert-Butyl-diphenyl-silanyloxy)-6-[1,3]dithian-2-yl-6-methyl-heptane-3,5-diol

Guidance literature:: Multi-step reaction with 11 steps

1.1: 91 percent / imidazole / dimethylformamide / 2 h / 20 °C

2.1: 83 percent / acetonitrile / 22 h / 20 °C

3.1: 95 percent / Bu₃SnH; AIBN / toluene / 0.83 h / 90 °C

4.1: 84 percent / Me₃Al; i-PrOH / hexane / 24 h / 20 °C

5.1: 77 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 48 h / 20 °C

6.1: 98 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 2.5 h / 20 °C

7.1: N-methylmorpholine N-oxide / tetra-n-propylammonium perruthenate / CH₂Cl₂ / 0.5 h / 20 °C

8.1: 3.48 g / potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 28 h / -78 - 20 °C

9.1: catecholborane / (Ph₃P)3RhCl / tetrahydrofuran / 2.25 h / 0 - 20 °C

9.2: 86 percent / H₂O₂; NaOH / tetrahydrofuran; methanol; H₂O / 0 - 20 °C

10.1: 76 percent / BF₃*Et₂O / CH₂Cl₂ / 5 h / -40 - -10 °C

11.1: 58 percent / imidazole / dimethylformamide / 0.5 h / 20 °C

With 1H-imidazole; 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; trimethylaluminum; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; 4-methylmorpholine N-oxide; isopropyl alcohol; benzo[1,3,2]dioxaborole; Wilkinson's catalyst; tetrapropylammonium perruthennate; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 3.1: Barton deoxygenation / 4.1: Meerwein-Ponndorf-Verley reduction / 8.1: Kocienski-Julia olefination;
DOI:10.1021/ol061626i

Reference yield:

: 913722-24-4
(2S,4S,6S)-6-Methoxy-4-(4-methoxy-benzyloxy)-5,5-dimethyl-tetrahydro-pyran-2-carbaldehyde

: 913722-28-8
(3R,5S)-1-(tert-Butyl-diphenyl-silanyloxy)-6-[1,3]dithian-2-yl-6-methyl-heptane-3,5-diol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 3.48 g / potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 28 h / -78 - 20 °C

2.1: catecholborane / (Ph₃P)3RhCl / tetrahydrofuran / 2.25 h / 0 - 20 °C

2.2: 86 percent / H₂O₂; NaOH / tetrahydrofuran; methanol; H₂O / 0 - 20 °C

3.1: 76 percent / BF₃*Et₂O / CH₂Cl₂ / 5 h / -40 - -10 °C

4.1: 58 percent / imidazole / dimethylformamide / 0.5 h / 20 °C

With 1H-imidazole; boron trifluoride diethyl etherate; potassium hexamethylsilazane; benzo[1,3,2]dioxaborole; Wilkinson's catalyst; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: Kocienski-Julia olefination;
DOI:10.1021/ol061626i