(4R,5S)-4-[(E)-(S)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-but-2-enyl]-5-benzyloxymethyl-oxazolidin-2-one

Base Information

Chemical Name:(4R,5S)-4-[(E)-(S)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-but-2-enyl]-5-benzyloxymethyl-oxazolidin-2-one
CAS No.:285556-00-5
Molecular Formula:C₂₈H₃₉NO₅Si
Molecular Weight:497.707
Hs Code.:

Synonyms:(4R,5S)-4-[(E)-(S)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-but-2-enyl]-5-benzyloxymethyl-oxazolidin-2-one

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Chemical Property of (4R,5S)-4-[(E)-(S)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-but-2-enyl]-5-benzyloxymethyl-oxazolidin-2-one

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Technology Process of (4R,5S)-4-[(E)-(S)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-but-2-enyl]-5-benzyloxymethyl-oxazolidin-2-one

There total 7 articles about (4R,5S)-4-[(E)-(S)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-but-2-enyl]-5-benzyloxymethyl-oxazolidin-2-one 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: 81.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 227627-07-8
(4S,5R,1'S,E)-4-[4'-benzyloxy-1'-(hydroxy)but-2'-enyl]-5-(benzyloxy)methyloxazolidin-2-one

: 285556-00-5
(4R,5S)-4-[(E)-(S)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-but-2-enyl]-5-benzyloxymethyl-oxazolidin-2-one

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 24h;
DOI:10.1021/ja000817s

Reference yield:

: 106319-54-4
(2E,5E)-1,7-di-O-benzyl-hepta-2,5-diene-1,4,7-triol

: 285556-00-5
(4R,5S)-4-[(E)-(S)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-but-2-enyl]-5-benzyloxymethyl-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: 86 percent / t-BuOOH; Ti(O-i-Pr)4; D-(-)-diisopropyl tartarate / 4A molecular sieves / CH₂Cl₂ / 96 h / -25 °C

2: 74 percent / Ph₃P; p-nitrobenzoic acid; diisopropyl azodicarboxylate / toluene / -78 - -30 °C

3: tetrahydrofuran / 0 - 20 °C

4: 19.3 g / K₂CO₃; n-Bu₄NCl / acetonitrile / 14 h / 20 °C

5: 75 percent / NaOMe; MeOH / 15 h / 20 °C

6: 81 percent / imidazole / dimethylformamide / 24 h / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; methanol; tert.-butylhydroperoxide; di-isopropyl azodicarboxylate; tetrabutyl-ammonium chloride; sodium methylate; potassium carbonate; D-(-)-diisopropyl tartrate; triphenylphosphine; 4-nitro-benzoic acid; 4 A molecular sieve; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 1: Oxidation / 2: Isomerization / 3: Addition / 4: Cyclization / 5: methanolysis / 6: silylation;
DOI:10.1021/ja000817s

Reference yield:

: 106319-55-5
(2R,3R,4R,E)-1,7-di-O-benzyl-2,3-epoxy-5-heptene-1,4,7-triol

: 285556-00-5
(4R,5S)-4-[(E)-(S)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-but-2-enyl]-5-benzyloxymethyl-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 5 steps

1: 74 percent / Ph₃P; p-nitrobenzoic acid; diisopropyl azodicarboxylate / toluene / -78 - -30 °C

2: tetrahydrofuran / 0 - 20 °C

3: 19.3 g / K₂CO₃; n-Bu₄NCl / acetonitrile / 14 h / 20 °C

4: 75 percent / NaOMe; MeOH / 15 h / 20 °C

5: 81 percent / imidazole / dimethylformamide / 24 h / 20 °C

With 1H-imidazole; methanol; di-isopropyl azodicarboxylate; tetrabutyl-ammonium chloride; sodium methylate; potassium carbonate; triphenylphosphine; 4-nitro-benzoic acid; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; acetonitrile; 1: Isomerization / 2: Addition / 3: Cyclization / 4: methanolysis / 5: silylation;
DOI:10.1021/ja000817s