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

Base Information

• Chemical Name: (17E)-1α-tert-butyldimethylsilyloxy-20-[4-(methyloxycarbonyl)phenyl]-17,20-didehydro-21,22,23,24,25,26,27-heptanorvitamin D₃ tert-butyldimethylsilyl ether
• CAS No.: 282724-88-3
• Molecular Formula: C₄₀H₆₂O₄Si₂
• Molecular Weight: 663.101

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

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

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

There total 6 articles about (17E)-1α-tert-butyldimethylsilyloxy-20-[4-(methyloxycarbonyl)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: 89.0%

[(2Z)-2-[(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide (81522-68-1) + (17E)-{1-[4-(methyloxycarbonyl)phenyl]methylidene}-de-A,B-androstan-8-one (282724-87-2) → (17E)-1α-tert-butyldimethylsilyloxy-20-[4-(methyloxycarbonyl)phenyl]-17,20-didehydro-21,22,23,24,25,26,27-heptanorvitamin D3 tert-butyldimethylsilyl ether (282724-88-3)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -78 - -40 ℃;

DOI:10.1021/jo000579j

Reference yield:

diethyl (4-bromobenzyl)phosphonate (38186-51-5) → (17E)-1α-tert-butyldimethylsilyloxy-20-[4-(methyloxycarbonyl)phenyl]-17,20-didehydro-21,22,23,24,25,26,27-heptanorvitamin D3 tert-butyldimethylsilyl ether (282724-88-3)

Guidance literature:

Multi-step reaction with 5 steps

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

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

3: 96 percent / aq. HF / acetonitrile / 3 h / 20 °C

4: 91 percent / PDC / CH₂Cl₂ / 8 h

5: 89 percent / n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C

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

DOI:10.1021/jo000579j

Reference yield:

8β-[(tert-butyldimethylsilyl)oxy]de-A,B-androstan-17β-one (140659-26-3) → (17E)-1α-tert-butyldimethylsilyloxy-20-[4-(methyloxycarbonyl)phenyl]-17,20-didehydro-21,22,23,24,25,26,27-heptanorvitamin D3 tert-butyldimethylsilyl ether (282724-88-3)

Guidance literature:

Multi-step reaction with 5 steps

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

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

3: 96 percent / aq. HF / acetonitrile / 3 h / 20 °C

4: 91 percent / PDC / CH₂Cl₂ / 8 h

5: 89 percent / n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C

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

DOI:10.1021/jo000579j

upstream raw materials:

[(2Z)-2-[(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide

(17E)-{1-[4-(methyloxycarbonyl)phenyl]methylidene}-de-A,B-androstan-8-one

diethyl (4-bromobenzyl)phosphonate

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

Downstream raw materials:

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

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