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

Base Information

Chemical Name:ethyl (2R,3S,4S)-4-(4-tert-butyldimethylsilyloxyphenyl)-4-tert-butyldiphenylsilyloxy-2-chloromethylsulfonyloxy-3-methylbutanoate
CAS No.:213976-26-2
Molecular Formula:C₃₆H₅₁ClO₇SSi₂
Molecular Weight:719.487
Hs Code.:

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

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

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

There total 12 articles about ethyl (2R,3S,4S)-4-(4-tert-butyldimethylsilyloxyphenyl)-4-tert-butyldiphenylsilyloxy-2-chloromethylsulfonyloxy-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: 91.0%

: 3518-65-8
monochloromethanesulfonyl chloride

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

: 213976-26-2
ethyl (2R,3S,4S)-4-(4-tert-butyldimethylsilyloxyphenyl)-4-tert-butyldiphenylsilyloxy-2-chloromethylsulfonyloxy-3-methylbutanoate

Guidance literature:: With pyridine; at 20 ℃; for 12h;
DOI:10.1016/S0040-4020(98)00647-4

Reference yield:

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

: 213976-26-2
ethyl (2R,3S,4S)-4-(4-tert-butyldimethylsilyloxyphenyl)-4-tert-butyldiphenylsilyloxy-2-chloromethylsulfonyloxy-3-methylbutanoate

Guidance literature:: Multi-step reaction with 9 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

9: 91 percent / pyridine / 12 h / 20 °C

With pyridine; 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 / 9: Substitution;
DOI:10.1016/S0040-4020(98)00647-4

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 213976-26-2
ethyl (2R,3S,4S)-4-(4-tert-butyldimethylsilyloxyphenyl)-4-tert-butyldiphenylsilyloxy-2-chloromethylsulfonyloxy-3-methylbutanoate

Guidance literature:: Multi-step reaction with 10 steps

1: 85 percent / imidazole / CH₂Cl₂ / 0.67 h / 0 °C

2: 36 percent / Zn dust / benzene / 1.5 h / Heating

3: 76 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / 0 °C

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

5: 97 percent / imidazole; 4-dimethylaminopyridine / CH₂Cl₂ / 44 h / 20 °C

6: 99 percent / HAl(i-Bu)2 / toluene / 1 h / -78 °C

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

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

9: 11 percent / O₃; dimethylsulfide / CH₂Cl₂ / 1.5 h / -78 °C

10: 91 percent / pyridine / 12 h / 20 °C

With pyridine; 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: Substitution / 2: Addition / 3: Reduction / 4: Acetylation / 5: Substitution / 6: reductive deacetylation / 7: Oxidation / 8: Addition / 9: ozonolysis / 10: Substitution;
DOI:10.1016/S0040-4020(98)00647-4