1α-<((tert-butyldiphenyl)silyl)oxy>-6,7-dehydro-25-hydroxyprevitamin D3 (tert-butyldiphenyl)silyl ether

Base Information

• Chemical Name: 1α-<((tert-butyldiphenyl)silyl)oxy>-6,7-dehydro-25-hydroxyprevitamin D3 (tert-butyldiphenyl)silyl ether
• CAS No.: 134458-47-2
• Molecular Formula: C₅₉H₇₈O₃Si₂
• Molecular Weight: 891.438
• Mol file: 134458-47-2.mol

Synonyms:1α-<((tert-butyldiphenyl)silyl)oxy>-6,7-dehydro-25-hydroxyprevitamin D3 (tert-butyldiphenyl)silyl ether

Chemical Property of 1α-<((tert-butyldiphenyl)silyl)oxy>-6,7-dehydro-25-hydroxyprevitamin D3 (tert-butyldiphenyl)silyl ether

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1α-<((tert-butyldiphenyl)silyl)oxy>-6,7-dehydro-25-hydroxyprevitamin D3 (tert-butyldiphenyl)silyl ether

There total 7 articles about 1α-<((tert-butyldiphenyl)silyl)oxy>-6,7-dehydro-25-hydroxyprevitamin 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: 84.0%

25-hydroxy-de-A,B-cholest-8-en-8-yl trifluoromethanesulfonate (134458-36-9) + (3S,5R)-3,5-bis<((tert-butyldiphenyl)silyl)oxy>-1-ethynyl-2-methylcyclohex-1-ene (134458-38-1) → 1α-<((tert-butyldiphenyl)silyl)oxy>-6,7-dehydro-25-hydroxyprevitamin D3 (tert-butyldiphenyl)silyl ether (134458-47-2)

Guidance literature:

With copper(l) iodide; bispalladium(II) acetate; diethylamine; In N,N-dimethyl-formamide; for 1.5h; Ambient temperature;

DOI:10.1021/ja00018a038

Reference yield:

(1S,2R,4S,6S)-2,4-diacetoxy-2-ethynyl-1-methyl-7-oxabicyclo<4.1.0>heptane (115540-14-2,146728-49-6) → 1α-<((tert-butyldiphenyl)silyl)oxy>-6,7-dehydro-25-hydroxyprevitamin D3 (tert-butyldiphenyl)silyl ether (134458-47-2)

Guidance literature:

Multi-step reaction with 3 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: 84 percent / diethylamine, CuI, bispalladium(II) acetate / dimethylformamide / 1.5 h / Ambient temperature

With 1H-imidazole; samarium; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,2-Diiodoethane; bispalladium(II) acetate; sodium methylate; diethylamine; In N,N-dimethyl-formamide;

DOI:10.1021/ja00018a038

Reference yield:

de-A,B-25-cholesta-8,25-dien-8-yl trifluromethanesulfonate (113490-28-1) → 1α-<((tert-butyldiphenyl)silyl)oxy>-6,7-dehydro-25-hydroxyprevitamin D3 (tert-butyldiphenyl)silyl ether (134458-47-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) mercuric acetate, 2.) aq. NaOH, NaBH₄ / 1.) THF, H₂O, RT, 1 h, 2.) THF, H₂O, RT, 30 min

2: 84 percent / diethylamine, CuI, bispalladium(II) acetate / dimethylformamide / 1.5 h / Ambient temperature

With sodium hydroxide; sodium tetrahydroborate; copper(l) iodide; bispalladium(II) acetate; mercury(II) diacetate; diethylamine; In N,N-dimethyl-formamide;

DOI:10.1021/ja00018a038

upstream raw materials:

25-hydroxy-de-A,B-cholest-8-en-8-yl trifluoromethanesulfonate

(3S,5R)-3,5-bis<((tert-butyldiphenyl)silyl)oxy>-1-ethynyl-2-methylcyclohex-1-ene

de-A,B-25-cholesta-8,25-dien-8-yl trifluromethanesulfonate

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

Downstream raw materials:

(1R,3S)-5-[(1R,3aR,7aR)-1-((1R)-5-hydroxy-1,5-dimethylhexyl)-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl]ethynyl-4-methylcyclohex-4-ene-1,3-diol

calcitriol

[2H]-Pre-1,25-D₃