(3S,5R,6R)-8-(tert-butyldiphenylsilyloxy)-1-(5,6-dihydro-2H-pyran-2-yl)-5-methyl-6-(triethylsilyloxy)octan-3-ol

Base Information

Chemical Name:(3S,5R,6R)-8-(tert-butyldiphenylsilyloxy)-1-(5,6-dihydro-2H-pyran-2-yl)-5-methyl-6-(triethylsilyloxy)octan-3-ol
CAS No.:836598-92-6
Molecular Formula:C₃₆H₅₈O₄Si₂
Molecular Weight:611.025
Hs Code.:

Synonyms:(3S,5R,6R)-8-(tert-butyldiphenylsilyloxy)-1-(5,6-dihydro-2H-pyran-2-yl)-5-methyl-6-(triethylsilyloxy)octan-3-ol

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Chemical Property of (3S,5R,6R)-8-(tert-butyldiphenylsilyloxy)-1-(5,6-dihydro-2H-pyran-2-yl)-5-methyl-6-(triethylsilyloxy)octan-3-ol

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Technology Process of (3S,5R,6R)-8-(tert-butyldiphenylsilyloxy)-1-(5,6-dihydro-2H-pyran-2-yl)-5-methyl-6-(triethylsilyloxy)octan-3-ol

There total 12 articles about (3S,5R,6R)-8-(tert-butyldiphenylsilyloxy)-1-(5,6-dihydro-2H-pyran-2-yl)-5-methyl-6-(triethylsilyloxy)octan-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:

: 474524-60-2
1-(tert-butyldimethylsilyloxy)-7-(trimethylsilyloxy)hept-4-yn-3-ol

: 836598-92-6
(3S,5R,6R)-8-(tert-butyldiphenylsilyloxy)-1-(5,6-dihydro-2H-pyran-2-yl)-5-methyl-6-(triethylsilyloxy)octan-3-ol

Guidance literature:: Multi-step reaction with 8 steps

1: 97 percent / K₂CO₃ / methanol / 0.5 h

2: 96 percent / H₂ / Lindlar catalyst / tetrahydrofuran / 1.5 h / 20 °C

3: 82 percent / DMAP; Et₃N / CH₂Cl₂ / 16.5 h / 0 - 20 °C

4: 75 percent / NaH / tetrahydrofuran / 16 h / 20 °C

5: 80 percent / Bu₄NF / tetrahydrofuran / 16 h / 20 °C

6: 89 percent / DMAP; Et₃N / CH₂Cl₂ / 0 - 20 °C

7: 91 percent / LiBr / acetone / 1.5 h / Heating

8: Mg; iodine; 1,2-dibromoethane / diethyl ether / 2 h / 0 - 20 °C

With dmap; tetrabutyl ammonium fluoride; hydrogen; iodine; sodium hydride; potassium carbonate; magnesium; ethylene dibromide; triethylamine; lithium bromide; Lindlar's catalyst; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetone; 8: Barbier reaction;
DOI:10.1039/b412883d

Reference yield:

: 836598-93-7
7-(tert-butyldimethylsilyloxy)hept-3-yn-1,5-diol

: 836598-92-6
(3S,5R,6R)-8-(tert-butyldiphenylsilyloxy)-1-(5,6-dihydro-2H-pyran-2-yl)-5-methyl-6-(triethylsilyloxy)octan-3-ol

Guidance literature:: Multi-step reaction with 7 steps

1: 96 percent / H₂ / Lindlar catalyst / tetrahydrofuran / 1.5 h / 20 °C

2: 82 percent / DMAP; Et₃N / CH₂Cl₂ / 16.5 h / 0 - 20 °C

3: 75 percent / NaH / tetrahydrofuran / 16 h / 20 °C

4: 80 percent / Bu₄NF / tetrahydrofuran / 16 h / 20 °C

5: 89 percent / DMAP; Et₃N / CH₂Cl₂ / 0 - 20 °C

6: 91 percent / LiBr / acetone / 1.5 h / Heating

7: Mg; iodine; 1,2-dibromoethane / diethyl ether / 2 h / 0 - 20 °C

With dmap; tetrabutyl ammonium fluoride; hydrogen; iodine; sodium hydride; magnesium; ethylene dibromide; triethylamine; lithium bromide; Lindlar's catalyst; In tetrahydrofuran; diethyl ether; dichloromethane; acetone; 7: Barbier reaction;
DOI:10.1039/b412883d