(2R,3S,4S)-1-(t-butyldiphenylsilyloxy)-2,3-isopropylidenedioxy-4-phenyl-1-trifluoromethanesulfonyloxybutane

Base Information

Chemical Name:(2R,3S,4S)-1-(t-butyldiphenylsilyloxy)-2,3-isopropylidenedioxy-4-phenyl-1-trifluoromethanesulfonyloxybutane
CAS No.:252273-62-4
Molecular Formula:C₃₀H₃₅F₃O₆SSi
Molecular Weight:608.751
Hs Code.:

Synonyms:(2R,3S,4S)-1-(t-butyldiphenylsilyloxy)-2,3-isopropylidenedioxy-4-phenyl-1-trifluoromethanesulfonyloxybutane

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Chemical Property of (2R,3S,4S)-1-(t-butyldiphenylsilyloxy)-2,3-isopropylidenedioxy-4-phenyl-1-trifluoromethanesulfonyloxybutane

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Technology Process of (2R,3S,4S)-1-(t-butyldiphenylsilyloxy)-2,3-isopropylidenedioxy-4-phenyl-1-trifluoromethanesulfonyloxybutane

There total 8 articles about (2R,3S,4S)-1-(t-butyldiphenylsilyloxy)-2,3-isopropylidenedioxy-4-phenyl-1-trifluoromethanesulfonyloxybutane 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: 99.0%

: 358-23-6
trifluoromethylsulfonic anhydride

: 252273-61-3
(1S,2S,3R)-1-(t-butyldiphenylsilyloxy)-2,3-isopropylidenedioxy-1-phenylbutan-4-ol

: 252273-62-4
(2R,3S,4S)-1-(t-butyldiphenylsilyloxy)-2,3-isopropylidenedioxy-4-phenyl-1-trifluoromethanesulfonyloxybutane

Guidance literature:: With 2,6-di-tert-butyl-4-methylpyridine; In dichloromethane; at -15 ℃; for 0.5h;
DOI:10.1016/S0040-4020(99)00794-2

Reference yield:

: 179618-34-9
ethyl (2S,3S,4R)-4-{[(tert-butyl)(dimethyl)silyl]oxy}-2,3-dihydroxy-4-phenylbutanoate

: 252273-62-4
(2R,3S,4S)-1-(t-butyldiphenylsilyloxy)-2,3-isopropylidenedioxy-4-phenyl-1-trifluoromethanesulfonyloxybutane

Guidance literature:: Multi-step reaction with 7 steps

1: 99 percent / camphorsulfonic acid / CH₂Cl₂ / 0.25 h / 20 °C

2: 95 percent / Et₃N*3HF / acetonitrile / 168 h / 20 °C

3: 97 percent / Ph₃P; ethyl azodicarboxylate / tetrahydrofuran / 1.75 h / 0 - 20 °C

4: 87 percent / K₂CO₃ / CH₂Cl₂; ethanol / 1 h / 20 °C

5: 94 percent / imidazole / dimethylformamide / 96 h / 20 °C

6: 98 percent / LiAlH₄ / diethyl ether / 0.08 h / 0 °C

7: 99 percent / 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 0.5 h / -15 °C

With 1H-imidazole; lithium aluminium tetrahydride; 2,6-di-tert-butyl-4-methylpyridine; ethyl azodicarboxylate; camphor-10-sulfonic acid; potassium carbonate; triethylamine tris(hydrogen fluoride); triphenylphosphine; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: Cyclization / 2: desilylation / 3: Mitsunobu reaction / 4: saponification / 5: silylation / 6: Reduction / 7: Substitution;
DOI:10.1016/S0040-4020(99)00794-2

Reference yield:

: 179618-33-8
ethyl (2E,4S)-4-{[(tert-butyl)(dimethyl)silyl]oxy}-4-phenylbut-2-enoate

: 252273-62-4
(2R,3S,4S)-1-(t-butyldiphenylsilyloxy)-2,3-isopropylidenedioxy-4-phenyl-1-trifluoromethanesulfonyloxybutane

Guidance literature:: Multi-step reaction with 8 steps

1: 97 percent / AD-mix-β; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 14 h / 20 °C

2: 99 percent / camphorsulfonic acid / CH₂Cl₂ / 0.25 h / 20 °C

3: 95 percent / Et₃N*3HF / acetonitrile / 168 h / 20 °C

4: 97 percent / Ph₃P; ethyl azodicarboxylate / tetrahydrofuran / 1.75 h / 0 - 20 °C

5: 87 percent / K₂CO₃ / CH₂Cl₂; ethanol / 1 h / 20 °C

6: 94 percent / imidazole / dimethylformamide / 96 h / 20 °C

7: 98 percent / LiAlH₄ / diethyl ether / 0.08 h / 0 °C

8: 99 percent / 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 0.5 h / -15 °C

With 1H-imidazole; lithium aluminium tetrahydride; 2,6-di-tert-butyl-4-methylpyridine; ethyl azodicarboxylate; methanesulfonamide; AD-mix-β; camphor-10-sulfonic acid; potassium carbonate; triethylamine tris(hydrogen fluoride); triphenylphosphine; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; 1: hydroxylation / 2: Cyclization / 3: desilylation / 4: Mitsunobu reaction / 5: saponification / 6: silylation / 7: Reduction / 8: Substitution;
DOI:10.1016/S0040-4020(99)00794-2