(+)-(1R,2S,4R)-4-(4-methoxybenzyloxy)-2-(tert-butyldiphenylsiloxymethyl)-2-vinylcyclobutanol

Base Information

• Chemical Name: (+)-(1R,2S,4R)-4-(4-methoxybenzyloxy)-2-(tert-butyldiphenylsiloxymethyl)-2-vinylcyclobutanol
• CAS No.: 1033126-32-7
• Molecular Formula: C₃₁H₃₈O₄Si
• Molecular Weight: 502.726
• Mol file: 1033126-32-7.mol

Synonyms:(+)-(1R,2S,4R)-4-(4-methoxybenzyloxy)-2-(tert-butyldiphenylsiloxymethyl)-2-vinylcyclobutanol

Chemical Property of (+)-(1R,2S,4R)-4-(4-methoxybenzyloxy)-2-(tert-butyldiphenylsiloxymethyl)-2-vinylcyclobutanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(1R,2S,4R)-4-(4-methoxybenzyloxy)-2-(tert-butyldiphenylsiloxymethyl)-2-vinylcyclobutanol

There total 11 articles about (+)-(1R,2S,4R)-4-(4-methoxybenzyloxy)-2-(tert-butyldiphenylsiloxymethyl)-2-vinylcyclobutanol 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: 60.0%

(-)-((2R,4R,5R)-4-(4-methoxybenzyloxy)-5-methoxy-2-vinyltetrahydrofuran-2-yl)methyl tert-butyldiphenylsilyl ether (685142-69-2) → (-)-(1S,2R,4R)-4-(4-methoxybenzyloxy)-2-(tert-butyldiphenylsiloxymethyl)-2-vinylcyclobutanol (685142-72-7) + (+)-(1R,2S,4R)-4-(4-methoxybenzyloxy)-2-(tert-butyldiphenylsiloxymethyl)-2-vinylcyclobutanol (1033126-32-7)

Guidance literature:

With n-butyllithium; zirconocene dichloride; In tetrahydrofuran; hexane; at -78 - 20 ℃;

DOI:10.1021/jo8004233

Reference yield:

(-)-((2S,4R,5R)-4-(4-methoxybenzyloxy)-5-methoxy-2-vinyltetrahydrofuran-2-yl)methyl tert-butyldiphenylsilyl ether (685142-71-6) → (-)-(1S,2R,4R)-4-(4-methoxybenzyloxy)-2-(tert-butyldiphenylsiloxymethyl)-2-vinylcyclobutanol (685142-72-7) + (+)-(1R,2S,4R)-4-(4-methoxybenzyloxy)-2-(tert-butyldiphenylsiloxymethyl)-2-vinylcyclobutanol (1033126-32-7)

Guidance literature:

With n-butyllithium; zirconocene dichloride; In tetrahydrofuran; at 20 - 55 ℃;

DOI:10.1016/j.tet.2003.07.012

Reference yield:

(-)-(2R,4R,5R)-methyl 4-(4-methoxybenzyloxy)-5-methoxytetrahydrofuran-2-carboxylate (685142-64-7) → (+)-(1R,2S,4R)-4-(4-methoxybenzyloxy)-2-(tert-butyldiphenylsiloxymethyl)-2-vinylcyclobutanol (1033126-32-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 59 percent / nBuLi; iPr₂NH / hexane; tetrahydrofuran / -78 - -10 °C

2: 94 percent / imidazole / dimethylformamide / 3 h / 20 °C

3: Dibal-H / CH₂Cl₂; hexane / 1 h / -20 °C

4: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 - 20 °C

5: 847 mg / nBuLi / tetrahydrofuran; hexane / 3 h / 20 °C

6: 21 mg / Cp₂ZrCl₂; nBuLi / tetrahydrofuran / 20 - 55 °C

With 1H-imidazole; n-butyllithium; zirconocene dichloride; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; 4: Swern oxidation / 5: Wittig olefination;

DOI:10.1016/j.tet.2003.07.012

upstream raw materials:

(-)-((2S,4R,5R)-4-(4-methoxybenzyloxy)-5-methoxy-2-vinyltetrahydrofuran-2-yl)methyl tert-butyldiphenylsilyl ether

(-)-((2R,4R,5R)-4-(4-methoxybenzyloxy)-5-methoxy-2-vinyltetrahydrofuran-2-yl)methyl tert-butyldiphenylsilyl ether

(-)-(2R,4R,5R)-methyl 4-(4-methoxybenzyloxy)-5-methoxytetrahydrofuran-2-carboxylate

(2S,4R,5R)-2-Hydroxymethyl-5-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-carboxylic acid methyl ester

Downstream raw materials:

tert-butyl(((1S,2R,3R)-2-(tert-butyldimethylsilyloxy)-3-(4-methoxybenzyloxy)-1-vinylcyclobutyl)methoxy)diphenylsilane