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

Base Information

• Chemical Name: (4S,5R,1'S,E)-4-[4'-benzyloxy-1'-(hydroxy)but-2'-enyl]-5-(benzyloxy)methyloxazolidin-2-one
• CAS No.: 227627-07-8
• Molecular Formula: C₂₂H₂₅NO₅
• Molecular Weight: 383.444
• Mol file: 227627-07-8.mol

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

Chemical Property of (4S,5R,1'S,E)-4-[4'-benzyloxy-1'-(hydroxy)but-2'-enyl]-5-(benzyloxy)methyloxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R,1'S,E)-4-[4'-benzyloxy-1'-(hydroxy)but-2'-enyl]-5-(benzyloxy)methyloxazolidin-2-one

There total 6 articles about (4S,5R,1'S,E)-4-[4'-benzyloxy-1'-(hydroxy)but-2'-enyl]-5-(benzyloxy)methyloxazolidin-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: 75.0%

(4R,5S,1'S,E)-4-[1'-benzoyloxy-2'-(benzyloxy)ethyl]-5-[3''-(benzyloxy)-prop-1''-enyl]oxazolidin-2-one (227627-05-6) → (4R,5S,1'S,E)-4-[2'-benzyloxy-1'-(hydroxy)ethyl]-5-[3''-(benzyloxy)prop-1''-enyl]oxazolidin-2-one + (4S,5R,1'S,E)-4-[4'-benzyloxy-1'-(hydroxy)but-2'-enyl]-5-(benzyloxy)methyloxazolidin-2-one (227627-07-8)

Guidance literature:

With methanol; sodium methylate;

DOI:10.1021/ja000817s

Reference yield:

(2E,5E)-1,7-di-O-benzyl-hepta-2,5-diene-1,4,7-triol (106319-54-4) → (4S,5R,1'S,E)-4-[4'-benzyloxy-1'-(hydroxy)but-2'-enyl]-5-(benzyloxy)methyloxazolidin-2-one (227627-07-8)

Guidance literature:

Multi-step reaction with 5 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

With 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; toluene; acetonitrile; 1: Oxidation / 2: Isomerization / 3: Addition / 4: Cyclization / 5: methanolysis;

DOI:10.1021/ja000817s

Reference yield:

(2R,3R,4R,E)-1,7-di-O-benzyl-2,3-epoxy-5-heptene-1,4,7-triol (106319-55-5) → (4S,5R,1'S,E)-4-[4'-benzyloxy-1'-(hydroxy)but-2'-enyl]-5-(benzyloxy)methyloxazolidin-2-one (227627-07-8)

Guidance literature:

Multi-step reaction with 4 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

With methanol; di-isopropyl azodicarboxylate; tetrabutyl-ammonium chloride; sodium methylate; potassium carbonate; triphenylphosphine; 4-nitro-benzoic acid; In tetrahydrofuran; toluene; acetonitrile; 1: Isomerization / 2: Addition / 3: Cyclization / 4: methanolysis;

DOI:10.1021/ja000817s

upstream raw materials:

(4R,5S,1'S,E)-4-[1'-benzoyloxy-2'-(benzyloxy)ethyl]-5-[3''-(benzyloxy)-prop-1''-enyl]oxazolidin-2-one

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

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

(2R,3R,4S,E)-1,7-dibenzyloxy-2,3-epoxy-5-hepten-4-ol

Downstream raw materials:

(4S,5S,1'S,E)-4-[4'-benzyloxy-1'-(tert-butyldimethylsilyloxy)but-2'-enyl]-5-(benzyloxy)methyl-3-methyloxazolidin-2-one

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