methyl (5S,2Z)-5-benzyloxycarbonylamino-2-t-butoxycarbonylamino-6-hydroxy-2-hexenoate

Base Information

Chemical Name:methyl (5S,2Z)-5-benzyloxycarbonylamino-2-t-butoxycarbonylamino-6-hydroxy-2-hexenoate
CAS No.:837410-88-5
Molecular Formula:C₂₀H₂₈N₂O₇
Molecular Weight:408.452
Hs Code.:

Synonyms:methyl (5S,2Z)-5-benzyloxycarbonylamino-2-t-butoxycarbonylamino-6-hydroxy-2-hexenoate

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Chemical Property of methyl (5S,2Z)-5-benzyloxycarbonylamino-2-t-butoxycarbonylamino-6-hydroxy-2-hexenoate

Chemical Property:

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Technology Process of methyl (5S,2Z)-5-benzyloxycarbonylamino-2-t-butoxycarbonylamino-6-hydroxy-2-hexenoate

There total 6 articles about methyl (5S,2Z)-5-benzyloxycarbonylamino-2-t-butoxycarbonylamino-6-hydroxy-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: 87.0%

: 837410-85-2
methyl (5S,2Z)-4-(3-benzyloxycarbonyl-2,2-dimethyl-1,3-oxazolidin-4-yl)-2-t-butoxycarbonylamino-2-butenoate

: 837410-88-5
methyl (5S,2Z)-5-benzyloxycarbonylamino-2-t-butoxycarbonylamino-6-hydroxy-2-hexenoate

Guidance literature:: With trifluoroacetic acid; In chloroform; at 20 ℃;
DOI:10.3987/COM-04-10206

Reference yield:

: 3160-47-2
N-(benzyloxycarbonyl)-L-aspartic acid 4-methyl ester

: 837410-88-5
methyl (5S,2Z)-5-benzyloxycarbonylamino-2-t-butoxycarbonylamino-6-hydroxy-2-hexenoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: HOBt; DCC / tetrahydrofuran / 0.5 h / 0 °C

1.2: 86 percent / NaBH₄ / tetrahydrofuran / 0.5 h / 0 °C

2.1: 87 percent / p-toluenesulfonic acid hydrate / acetone / 20 °C

3.1: 91 percent / NaBH₄; CaCl₂ / ethanol / 0 °C

4.1: SO₃*pyridine; Et₃N / CHCl₃; dimethylsulfoxide / 1 h / 0 °C

5.1: 8.0 g / DBU / CHCl₃ / 0 - 20 °C

6.1: 87 percent / TFA / CHCl₃ / 20 °C

With sodium tetrahydroborate; pyridine-SO₃ complex; benzotriazol-1-ol; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; calcium chloride; In tetrahydrofuran; ethanol; chloroform; dimethyl sulfoxide; acetone;
DOI:10.3987/COM-04-10206

Reference yield:

: 192517-47-8
methyl (3S)-3-[[(benzyloxy)carbonyl]amino]-4-hydroxybutanoate

: 837410-88-5
methyl (5S,2Z)-5-benzyloxycarbonylamino-2-t-butoxycarbonylamino-6-hydroxy-2-hexenoate

Guidance literature:: Multi-step reaction with 5 steps

1: 87 percent / p-toluenesulfonic acid hydrate / acetone / 20 °C

2: 91 percent / NaBH₄; CaCl₂ / ethanol / 0 °C

3: SO₃*pyridine; Et₃N / CHCl₃; dimethylsulfoxide / 1 h / 0 °C

4: 8.0 g / DBU / CHCl₃ / 0 - 20 °C

5: 87 percent / TFA / CHCl₃ / 20 °C

With sodium tetrahydroborate; pyridine-SO₃ complex; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic acid; calcium chloride; In ethanol; chloroform; dimethyl sulfoxide; acetone;
DOI:10.3987/COM-04-10206