(17Z)-1α-tert-butyldimethylsilyloxy-20-[4-(dimethylhydroxymethyl)phenyl]-17,20-didehydro-21,22,23,24,25,26,27-heptanorvitamin D₃ tert-butyldimethylsilyl ether

Base Information

• Chemical Name: (17Z)-1α-tert-butyldimethylsilyloxy-20-[4-(dimethylhydroxymethyl)phenyl]-17,20-didehydro-21,22,23,24,25,26,27-heptanorvitamin D₃ tert-butyldimethylsilyl ether
• CAS No.: 282724-93-0
• Molecular Formula: C₄₁H₆₆O₃Si₂
• Molecular Weight: 663.144

Synonyms:(17Z)-1α-tert-butyldimethylsilyloxy-20-[4-(dimethylhydroxymethyl)phenyl]-17,20-didehydro-21,22,23,24,25,26,27-heptanorvitamin D₃ tert-butyldimethylsilyl ether

Chemical Property of (17Z)-1α-tert-butyldimethylsilyloxy-20-[4-(dimethylhydroxymethyl)phenyl]-17,20-didehydro-21,22,23,24,25,26,27-heptanorvitamin D₃ tert-butyldimethylsilyl ether

Chemical Property:

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Technology Process of (17Z)-1α-tert-butyldimethylsilyloxy-20-[4-(dimethylhydroxymethyl)phenyl]-17,20-didehydro-21,22,23,24,25,26,27-heptanorvitamin D₃ tert-butyldimethylsilyl ether

There total 8 articles about (17Z)-1α-tert-butyldimethylsilyloxy-20-[4-(dimethylhydroxymethyl)phenyl]-17,20-didehydro-21,22,23,24,25,26,27-heptanorvitamin D₃ tert-butyldimethylsilyl 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: 93.0%

methyllithium (917-54-4) + (17Z)-1α-tert-butyldimethylsilyloxy-20-[4-(methyloxycarbonyl)phenyl]-17,20-didehydro-21,22,23,24,25,26,27-heptanorvitamin D3 tert-butyldimethylsilyl ether (282724-92-9) → (17Z)-1α-tert-butyldimethylsilyloxy-20-[4-(dimethylhydroxymethyl)phenyl]-17,20-didehydro-21,22,23,24,25,26,27-heptanorvitamin D3 tert-butyldimethylsilyl ether (282724-93-0)

Guidance literature:

In tetrahydrofuran; diethyl ether; at -78 ℃; for 0.75h;

DOI:10.1021/jo000579j

Reference yield:

diethyl (4-bromobenzyl)phosphonate (38186-51-5) → (17Z)-1α-tert-butyldimethylsilyloxy-20-[4-(dimethylhydroxymethyl)phenyl]-17,20-didehydro-21,22,23,24,25,26,27-heptanorvitamin D3 tert-butyldimethylsilyl ether (282724-93-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 13 percent / KH / tetrahydrofuran / 4 h / Heating

2: 80 percent / Et₃N; dppp / Pd(OAc)2 / dimethylsulfoxide / 12 h / 80 °C

3: 75 percent / tetrahydrofuran / 1.5 h / Irradiation

4: 92 percent / aq. HF / acetonitrile / 3 h / 20 °C

5: 96 percent / PDC / CH₂Cl₂ / 8 h

6: 82 percent / n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C

7: 93 percent / tetrahydrofuran; diethyl ether / 0.75 h / -78 °C

With dipyridinium dichromate; n-butyllithium; 1,3-bis-(diphenylphosphino)propane; hydrogen fluoride; potassium hydride; triethylamine; palladium diacetate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; acetonitrile; 1: Condensation / 2: Addition / 3: Isomerization / 4: Decomposition / 5: Oxidation / 6: Condensation / 7: Grignard reaction;

DOI:10.1021/jo000579j

Reference yield:

8β-[(tert-butyldimethylsilyl)oxy]de-A,B-androstan-17β-one (140659-26-3) → (17Z)-1α-tert-butyldimethylsilyloxy-20-[4-(dimethylhydroxymethyl)phenyl]-17,20-didehydro-21,22,23,24,25,26,27-heptanorvitamin D3 tert-butyldimethylsilyl ether (282724-93-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 13 percent / KH / tetrahydrofuran / 4 h / Heating

2: 80 percent / Et₃N; dppp / Pd(OAc)2 / dimethylsulfoxide / 12 h / 80 °C

3: 75 percent / tetrahydrofuran / 1.5 h / Irradiation

4: 92 percent / aq. HF / acetonitrile / 3 h / 20 °C

5: 96 percent / PDC / CH₂Cl₂ / 8 h

6: 82 percent / n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C

7: 93 percent / tetrahydrofuran; diethyl ether / 0.75 h / -78 °C

With dipyridinium dichromate; n-butyllithium; 1,3-bis-(diphenylphosphino)propane; hydrogen fluoride; potassium hydride; triethylamine; palladium diacetate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; acetonitrile; 1: Condensation / 2: Addition / 3: Isomerization / 4: Decomposition / 5: Oxidation / 6: Condensation / 7: Grignard reaction;

DOI:10.1021/jo000579j

upstream raw materials:

methyllithium

(17Z)-1α-tert-butyldimethylsilyloxy-20-[4-(methyloxycarbonyl)phenyl]-17,20-didehydro-21,22,23,24,25,26,27-heptanorvitamin D₃ tert-butyldimethylsilyl ether

diethyl (4-bromobenzyl)phosphonate

8β-[(tert-butyldimethylsilyl)oxy]de-A,B-androstan-17β-one

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