methyl (2Z,4S,5S)-5-[(tert-butyloxycarbonyl)amino]-4-(benzyloxy)-2-hexenoate

Base Information

• Chemical Name: methyl (2Z,4S,5S)-5-[(tert-butyloxycarbonyl)amino]-4-(benzyloxy)-2-hexenoate
• CAS No.: 614733-28-7
• Molecular Formula: C₁₉H₂₇NO₅
• Molecular Weight: 349.427
• Mol file: 614733-28-7.mol

Synonyms:

Chemical Property of methyl (2Z,4S,5S)-5-[(tert-butyloxycarbonyl)amino]-4-(benzyloxy)-2-hexenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2Z,4S,5S)-5-[(tert-butyloxycarbonyl)amino]-4-(benzyloxy)-2-hexenoate

There total 7 articles about methyl (2Z,4S,5S)-5-[(tert-butyloxycarbonyl)amino]-4-(benzyloxy)-2-hexenoate 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:

(3R,4S)-1-(4-methoxyphenyl)-3-(benzyloxy)-4-(hydroxymethyl)-2-azetidinone (160237-99-0) → methyl (2Z,4S,5S)-5-[(tert-butyloxycarbonyl)amino]-4-(benzyloxy)-2-hexenoate (614733-28-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 100 percent / 4-(dimethylamino)pyridine; Et₃N / CH₂Cl₂ / 6 h / 20 °C

2: 68 percent / NaI; NaHCO₃ / dimethylformamide / 6 h / 60 - 70 °C

3: 92 percent / NaHCO₃; H₂ / Pd/C / ethanol / 2 h / 2585.74 Torr

4: 76 percent / (NH₄)2Ce(NO₃)6 / H₂O; acetonitrile / 0.5 h / 0 °C

5: 93 percent / 4-(dimethylamino)pyridine / acetonitrile / 4 h / 20 °C

6: 87 percent / LiAlH₄ / tetrahydrofuran / 0.17 h / 0 °C

7: 2-iodoxybenzoic acid / dimethylsulfoxide / 3 h / 20 °C

8: methanol / 12 h / 20 °C

With dmap; lithium aluminium tetrahydride; ammonium cerium(IV) nitrate; hydrogen; sodium hydrogencarbonate; triethylamine; sodium iodide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4020(03)01063-9

Reference yield:

(-)-(3R,4S)-trans-3-benzyloxy-4-formyl-1-(p-methoxyphenyl)-2-azetidinone (160334-80-5) → methyl (2Z,4S,5S)-5-[(tert-butyloxycarbonyl)amino]-4-(benzyloxy)-2-hexenoate (614733-28-7)

Guidance literature:

Multi-step reaction with 9 steps

1: NaBH₄ / tetrahydrofuran; H₂O / 0 - 20 °C

2: 100 percent / 4-(dimethylamino)pyridine; Et₃N / CH₂Cl₂ / 6 h / 20 °C

3: 68 percent / NaI; NaHCO₃ / dimethylformamide / 6 h / 60 - 70 °C

4: 92 percent / NaHCO₃; H₂ / Pd/C / ethanol / 2 h / 2585.74 Torr

5: 76 percent / (NH₄)2Ce(NO₃)6 / H₂O; acetonitrile / 0.5 h / 0 °C

6: 93 percent / 4-(dimethylamino)pyridine / acetonitrile / 4 h / 20 °C

7: 87 percent / LiAlH₄ / tetrahydrofuran / 0.17 h / 0 °C

8: 2-iodoxybenzoic acid / dimethylsulfoxide / 3 h / 20 °C

9: methanol / 12 h / 20 °C

With dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; ammonium cerium(IV) nitrate; hydrogen; sodium hydrogencarbonate; triethylamine; sodium iodide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4020(03)01063-9

Reference yield:

(+)-(3R,4R)-1-(p-anisyl)-4-iodomethyl-3-(benzyloxy)-2-azetidinone (614733-16-3) → methyl (2Z,4S,5S)-5-[(tert-butyloxycarbonyl)amino]-4-(benzyloxy)-2-hexenoate (614733-28-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 92 percent / NaHCO₃; H₂ / Pd/C / ethanol / 2 h / 2585.74 Torr

2: 76 percent / (NH₄)2Ce(NO₃)6 / H₂O; acetonitrile / 0.5 h / 0 °C

3: 93 percent / 4-(dimethylamino)pyridine / acetonitrile / 4 h / 20 °C

4: 87 percent / LiAlH₄ / tetrahydrofuran / 0.17 h / 0 °C

5: 2-iodoxybenzoic acid / dimethylsulfoxide / 3 h / 20 °C

6: methanol / 12 h / 20 °C

With dmap; lithium aluminium tetrahydride; ammonium cerium(IV) nitrate; hydrogen; sodium hydrogencarbonate; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; water; dimethyl sulfoxide; acetonitrile;

DOI:10.1016/S0040-4020(03)01063-9

upstream raw materials:

methyl (triphenylphosphoranylidene)acetate

(2R,3S)-3-[(tert-butyloxycarbonyl)amino]-2-(benzyloxy)butanal

(3R,4S)-1-(4-methoxyphenyl)-3-(benzyloxy)-4-(hydroxymethyl)-2-azetidinone

(-)-(3R,4S)-trans-3-benzyloxy-4-formyl-1-(p-methoxyphenyl)-2-azetidinone

Downstream raw materials:

(+)-(5S,6S)-1-benzyl-5-(benzyloxy)-6-methyl-1,2,5,6-tetrahydro-2-pyridinone

(+)-(5S,6S)-5-(benzyloxy)-6-methyl-1,2,5,6-tetrahydro-2-pyridinone

(-)-(5S,6S)-1-benzyl-5-(benzyloxy)6-methyl-hexahydro-2-pyridinone