1α-<((tert-butyldiphenyl)silyl)oxy>-6,7-dehydro-25-hydroxy-9,14,19,19,19-pentadeuterioprevitamin D3 (tert-butyldiphenyl)silyl ether

Base Information

Chemical Name:1α-<((tert-butyldiphenyl)silyl)oxy>-6,7-dehydro-25-hydroxy-9,14,19,19,19-pentadeuterioprevitamin D3 (tert-butyldiphenyl)silyl ether
CAS No.:134458-48-3
Molecular Formula:C₅₉H₇₈O₃Si₂
Molecular Weight:896.398
Hs Code.:

Synonyms:1α-<((tert-butyldiphenyl)silyl)oxy>-6,7-dehydro-25-hydroxy-9,14,19,19,19-pentadeuterioprevitamin D3 (tert-butyldiphenyl)silyl ether

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Chemical Property of 1α-<((tert-butyldiphenyl)silyl)oxy>-6,7-dehydro-25-hydroxy-9,14,19,19,19-pentadeuterioprevitamin D3 (tert-butyldiphenyl)silyl ether

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Technology Process of 1α-<((tert-butyldiphenyl)silyl)oxy>-6,7-dehydro-25-hydroxy-9,14,19,19,19-pentadeuterioprevitamin D3 (tert-butyldiphenyl)silyl ether

There total 14 articles about 1α-<((tert-butyldiphenyl)silyl)oxy>-6,7-dehydro-25-hydroxy-9,14,19,19,19-pentadeuterioprevitamin D3 (tert-butyldiphenyl)silyl ether 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: 81.0%

: 134458-37-0
9,14-dideuterio-25-hydroxy-de-A,B-cholest-8-en-8-yl trifluoromethanesulfonate

: 134458-39-2
(3S,5R)-3,5-bis<((tert-butyldiphenyl)silyl)oxy>-1-ethynyl-2-(trideuteriomethyl)cyclohex-1-ene

: 134458-48-3
1α-<((tert-butyldiphenyl)silyl)oxy>-6,7-dehydro-25-hydroxy-9,14,19,19,19-pentadeuterioprevitamin D3 (tert-butyldiphenyl)silyl ether

Guidance literature:: With copper(l) iodide; bispalladium(II) acetate; diethylamine; In N,N-dimethyl-formamide; for 2.5h; Ambient temperature;
DOI:10.1021/ja00018a038

Reference yield:

: 113375-51-2
(3S,5R)-1-ethynyl-3,5-dihydroxy-2-methylcyclohex-1-ene

: 134458-48-3
1α-<((tert-butyldiphenyl)silyl)oxy>-6,7-dehydro-25-hydroxy-9,14,19,19,19-pentadeuterioprevitamin D3 (tert-butyldiphenyl)silyl ether

Guidance literature:: Multi-step reaction with 8 steps

1: 14.6 g / imidazole / dimethylformamide / 16 h / Ambient temperature

2: 90 percent / H₂, quinoline / Lindlar catalyst / hexane / 0.25 h / Ambient temperature

3: 64 percent / osmium tetraoxide, sodium periodate / tetrahydrofuran; H₂O / 46 h / Ambient temperature

4: 92 percent / 4A molecular sives / diethyl ether / 12 h / Ambient temperature

5: 84 percent / D₂O / 9 h / 150 °C

6: 1.) zinc, triphenylphosphine / 1.) CH₂Cl₂, RT, 23 h, 2.) CH₂Cl₂, RT, 1 h

7: 91 percent / n-BuLi / diethyl ether; hexane / 1.) -78 deg C, 10 min, 2.) 1 h

8: 81 percent / diethylamine, CuI, bispalladium(II) acetate / dimethylformamide / 2.5 h / Ambient temperature

With 1H-imidazole; quinoline; sodium periodate; copper(l) iodide; osmium(VIII) oxide; n-butyllithium; bispalladium(II) acetate; 4A molecular sives; hydrogen; water-d2; diethylamine; triphenylphosphine; zinc; Lindlar's catalyst; In tetrahydrofuran; diethyl ether; hexane; water; N,N-dimethyl-formamide;
DOI:10.1021/ja00018a038

Reference yield:

: 115540-14-2,146728-49-6
(1S,2R,4S,6S)-2,4-diacetoxy-2-ethynyl-1-methyl-7-oxabicyclo<4.1.0>heptane

: 134458-48-3
1α-<((tert-butyldiphenyl)silyl)oxy>-6,7-dehydro-25-hydroxy-9,14,19,19,19-pentadeuterioprevitamin D3 (tert-butyldiphenyl)silyl ether

Guidance literature:: Multi-step reaction with 9 steps

1: 1.) 1,2-diiodoethane, samarium, Pd(PPh₃)4, 2.) 0.2 M sodium methoxide / 1.) THF, RT, 8 h, 2.) methanol, 0 deg C, 4 h

2: 14.6 g / imidazole / dimethylformamide / 16 h / Ambient temperature

3: 90 percent / H₂, quinoline / Lindlar catalyst / hexane / 0.25 h / Ambient temperature

4: 64 percent / osmium tetraoxide, sodium periodate / tetrahydrofuran; H₂O / 46 h / Ambient temperature

5: 92 percent / 4A molecular sives / diethyl ether / 12 h / Ambient temperature

6: 84 percent / D₂O / 9 h / 150 °C

7: 1.) zinc, triphenylphosphine / 1.) CH₂Cl₂, RT, 23 h, 2.) CH₂Cl₂, RT, 1 h

8: 91 percent / n-BuLi / diethyl ether; hexane / 1.) -78 deg C, 10 min, 2.) 1 h

9: 81 percent / diethylamine, CuI, bispalladium(II) acetate / dimethylformamide / 2.5 h / Ambient temperature

With 1H-imidazole; quinoline; samarium; sodium periodate; copper(l) iodide; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; 1,2-Diiodoethane; bispalladium(II) acetate; 4A molecular sives; hydrogen; water-d2; sodium methylate; diethylamine; triphenylphosphine; zinc; Lindlar's catalyst; In tetrahydrofuran; diethyl ether; hexane; water; N,N-dimethyl-formamide;
DOI:10.1021/ja00018a038