ethyl (2R,3S,4S)-4-(4-tert-butyldimethylsilyloxyphenyl)-4-tert-butyldiphenylsilyloxy-2-hydroxy-3-methylbutanoate

Base Information

Chemical Name:ethyl (2R,3S,4S)-4-(4-tert-butyldimethylsilyloxyphenyl)-4-tert-butyldiphenylsilyloxy-2-hydroxy-3-methylbutanoate
CAS No.:172277-20-2
Molecular Formula:C₃₅H₅₀O₅Si₂
Molecular Weight:606.95
Hs Code.:

Synonyms:ethyl (2R,3S,4S)-4-(4-tert-butyldimethylsilyloxyphenyl)-4-tert-butyldiphenylsilyloxy-2-hydroxy-3-methylbutanoate

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Chemical Property of ethyl (2R,3S,4S)-4-(4-tert-butyldimethylsilyloxyphenyl)-4-tert-butyldiphenylsilyloxy-2-hydroxy-3-methylbutanoate

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Technology Process of ethyl (2R,3S,4S)-4-(4-tert-butyldimethylsilyloxyphenyl)-4-tert-butyldiphenylsilyloxy-2-hydroxy-3-methylbutanoate

There total 17 articles about ethyl (2R,3S,4S)-4-(4-tert-butyldimethylsilyloxyphenyl)-4-tert-butyldiphenylsilyloxy-2-hydroxy-3-methylbutanoate 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: 47.0%

: 5-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-5-(tert-butyl-diphenyl-silanyloxy)-2-ethoxy-4-methyl-pent-1-en-3-ol

: 172170-19-3
ethyl (2S,3S,4S)-4-(4-tert-butyldimethylsilyloxyphenyl)-4-tert-butyldiphenylsilyloxy-2-hydroxy-3-methylbutanoate

: 172277-20-2
ethyl (2R,3S,4S)-4-(4-tert-butyldimethylsilyloxyphenyl)-4-tert-butyldiphenylsilyloxy-2-hydroxy-3-methylbutanoate

Guidance literature:: With dimethylsulfide; ozone; In dichloromethane; at -78 ℃; for 1.5h;
DOI:10.1016/S0040-4020(98)00647-4

Reference yield:

: 120743-99-9
p-[(tert-butyldimethylsilyl)oxy]benzaldehyde

: 172277-20-2
ethyl (2R,3S,4S)-4-(4-tert-butyldimethylsilyloxyphenyl)-4-tert-butyldiphenylsilyloxy-2-hydroxy-3-methylbutanoate

Guidance literature:: Multi-step reaction with 8 steps

1: 36 percent / Zn dust / benzene / 1.5 h / Heating

2: 76 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / 0 °C

3: Amano P lipase / various solvent(s) / 7 h / 33 °C / Enzymatic reaction

4: 97 percent / imidazole; 4-dimethylaminopyridine / CH₂Cl₂ / 44 h / 20 °C

5: 99 percent / HAl(i-Bu)2 / toluene / 1 h / -78 °C

6: oxalyl chloride; Et₃N / CH₂Cl₂; dimethylsulfoxide / 1.67 h / -78 °C

7: tert-BuLi / tetrahydrofuran; pentane / 2 h / -78 °C

8: 11 percent / O₃; dimethylsulfide / CH₂Cl₂ / 1.5 h / -78 °C

With 1H-imidazole; dmap; lithium aluminium tetrahydride; oxalyl dichloride; dimethylsulfide; Amano P lipase; tert.-butyl lithium; diisobutylaluminium hydride; ozone; triethylamine; zinc; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; toluene; pentane; benzene; 1: Addition / 2: Reduction / 3: Acetylation / 4: Substitution / 5: reductive deacetylation / 6: Oxidation / 7: Addition / 8: ozonolysis;
DOI:10.1016/S0040-4020(98)00647-4

Reference yield:

: 172170-12-6
(+/-)-methyl 3-(4-tert-butyldimethylsilyloxyphenyl)-2-methyl-3-oxopropanoate

: 172277-20-2
ethyl (2R,3S,4S)-4-(4-tert-butyldimethylsilyloxyphenyl)-4-tert-butyldiphenylsilyloxy-2-hydroxy-3-methylbutanoate

Guidance literature:: Multi-step reaction with 8 steps

1: 6.2 percent / Zn(BH₄)2-Et₂O / diethyl ether / 4 h / -20 °C

2: 76 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / 0 °C

3: Amano P lipase / various solvent(s) / 7 h / 33 °C / Enzymatic reaction

4: 97 percent / imidazole; 4-dimethylaminopyridine / CH₂Cl₂ / 44 h / 20 °C

5: 99 percent / HAl(i-Bu)2 / toluene / 1 h / -78 °C

6: oxalyl chloride; Et₃N / CH₂Cl₂; dimethylsulfoxide / 1.67 h / -78 °C

7: tert-BuLi / tetrahydrofuran; pentane / 2 h / -78 °C

8: 11 percent / O₃; dimethylsulfide / CH₂Cl₂ / 1.5 h / -78 °C

With 1H-imidazole; dmap; lithium aluminium tetrahydride; oxalyl dichloride; dimethylsulfide; Zn(BH₄)2*Et₂O; Amano P lipase; tert.-butyl lithium; diisobutylaluminium hydride; ozone; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; toluene; pentane; 1: Reduction / 2: Reduction / 3: Acetylation / 4: Substitution / 5: reductive deacetylation / 6: Oxidation / 7: Addition / 8: ozonolysis;
DOI:10.1016/S0040-4020(98)00647-4