1α-<(tert-butyldimethylsilyl)-oxy>-6,7-didehydro-24-(methoxycarbonyl)-25,26,27-trisnorprevitamin D₃ tert-butyldimethylsilyl ether

Base Information

• Chemical Name: 1α-<(tert-butyldimethylsilyl)-oxy>-6,7-didehydro-24-(methoxycarbonyl)-25,26,27-trisnorprevitamin D₃ tert-butyldimethylsilyl ether
• CAS No.: 145372-41-4
• Molecular Formula: C₃₈H₆₆O₄Si₂
• Molecular Weight: 643.111
• Mol file: 145372-41-4.mol

Synonyms:1α-<(tert-butyldimethylsilyl)-oxy>-6,7-didehydro-24-(methoxycarbonyl)-25,26,27-trisnorprevitamin D₃ tert-butyldimethylsilyl ether

Chemical Property of 1α-<(tert-butyldimethylsilyl)-oxy>-6,7-didehydro-24-(methoxycarbonyl)-25,26,27-trisnorprevitamin D₃ tert-butyldimethylsilyl ether

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1α-<(tert-butyldimethylsilyl)-oxy>-6,7-didehydro-24-(methoxycarbonyl)-25,26,27-trisnorprevitamin D₃ tert-butyldimethylsilyl ether

There total 5 articles about 1α-<(tert-butyldimethylsilyl)-oxy>-6,7-didehydro-24-(methoxycarbonyl)-25,26,27-trisnorprevitamin 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: 86.0%

TB (116506-67-3) + methyl-des-A,B-8-<(trifluoromethanesulfonyl)oxy>chol-8-ene-24-carboxylate (145372-34-5) → 1α-<(tert-butyldimethylsilyl)-oxy>-6,7-didehydro-24-(methoxycarbonyl)-25,26,27-trisnorprevitamin D3 tert-butyldimethylsilyl ether (145372-41-4)

Guidance literature:

With triethylamine; bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; at 75 ℃; for 1h;

DOI:10.1021/jo00053a023

Reference yield:

(8S,20S)-de-A,B-20-(hydroxymethyl)pregnan-8-ol (64190-52-9) → 1α-<(tert-butyldimethylsilyl)-oxy>-6,7-didehydro-24-(methoxycarbonyl)-25,26,27-trisnorprevitamin D3 tert-butyldimethylsilyl ether (145372-41-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 96 percent / Ph₃P, imidazole, I₂ / tetrahydrofuran / -20 deg C, 15 min then RT, 1.5 h

2: 90 percent / PDC / CH₂Cl₂ / 6 h / Ambient temperature

3: 92 percent / LDA / tetrahydrofuran / 2 h / -78 °C

4: 65 percent / CuI, Zn / ethanol; H₂O / 0.67 h / sonication

5: 86 percent / Et₃N / (Ph₃P)2PdCl₂ / dimethylformamide / 1 h / 75 °C

With 1H-imidazole; copper(l) iodide; dipyridinium dichromate; iodine; triethylamine; triphenylphosphine; zinc; lithium diisopropyl amide; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo00053a023

Reference yield:

(1R,3aR,4S,7aR)-octahydro-1-[(S)-1-iodopropan-2-yl]-7a-methyl-1H-inden-4-ol (116535-65-0) → 1α-<(tert-butyldimethylsilyl)-oxy>-6,7-didehydro-24-(methoxycarbonyl)-25,26,27-trisnorprevitamin D3 tert-butyldimethylsilyl ether (145372-41-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / PDC / CH₂Cl₂ / 6 h / Ambient temperature

2: 92 percent / LDA / tetrahydrofuran / 2 h / -78 °C

3: 65 percent / CuI, Zn / ethanol; H₂O / 0.67 h / sonication

4: 86 percent / Et₃N / (Ph₃P)2PdCl₂ / dimethylformamide / 1 h / 75 °C

With copper(l) iodide; dipyridinium dichromate; triethylamine; zinc; lithium diisopropyl amide; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo00053a023

upstream raw materials:

TB

methyl-des-A,B-8-<(trifluoromethanesulfonyl)oxy>chol-8-ene-24-carboxylate

(8S,20S)-de-A,B-20-(hydroxymethyl)pregnan-8-ol

(1R,3aR,4S,7aR)-octahydro-1-[(S)-1-iodopropan-2-yl]-7a-methyl-1H-inden-4-ol

Downstream raw materials:

1α-[(tert-butyldimethylsilyl)oxy]-24-(methoxycarbonyl)-25,26,27-trisnorvitamin D3 tert-butyldimethylsilyl ether

(1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-9,10-secocholesta-5(Z),7(E),10(19)-trien-25-ol

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