methyl 2-((2S,3S)-2-benzoyloxy-4-hydroxy-3-(N-phenylmethoxycarbonyl)amino)butylpropenoate

Base Information

Chemical Name:methyl 2-((2S,3S)-2-benzoyloxy-4-hydroxy-3-(N-phenylmethoxycarbonyl)amino)butylpropenoate
CAS No.:288852-12-0
Molecular Formula:C₂₃H₂₅NO₇
Molecular Weight:427.454
Hs Code.:

Synonyms:methyl 2-((2S,3S)-2-benzoyloxy-4-hydroxy-3-(N-phenylmethoxycarbonyl)amino)butylpropenoate

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Chemical Property of methyl 2-((2S,3S)-2-benzoyloxy-4-hydroxy-3-(N-phenylmethoxycarbonyl)amino)butylpropenoate

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Technology Process of methyl 2-((2S,3S)-2-benzoyloxy-4-hydroxy-3-(N-phenylmethoxycarbonyl)amino)butylpropenoate

There total 8 articles about methyl 2-((2S,3S)-2-benzoyloxy-4-hydroxy-3-(N-phenylmethoxycarbonyl)amino)butylpropenoate 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: 88.0%

: 288852-11-9
methyl 2-((2S,3S)-2-benzoyloxy-4-(4-methoxyphenyl)methoxy-3-(N-phenylmethoxycarbonyl)amino)butylpropenoate

: 288852-12-0
methyl 2-((2S,3S)-2-benzoyloxy-4-hydroxy-3-(N-phenylmethoxycarbonyl)amino)butylpropenoate

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; for 1.5h;
DOI:10.1021/ol990320r

Reference yield:

: 4224-69-5
methyl 2-(bromomethyl)propenoate

: 288852-12-0
methyl 2-((2S,3S)-2-benzoyloxy-4-hydroxy-3-(N-phenylmethoxycarbonyl)amino)butylpropenoate

Guidance literature:: Multi-step reaction with 3 steps

1: 37 percent / indium / tetrahydrofuran; H₂O / 4.5 h

2: 64 percent / di-tert-butyl azodicarboxylate; Ph₃P / tetrahydrofuran / 20 °C

3: 88 percent / 2,3-dichloro-5,6-dicyanobenzoquinone / H₂O; CH₂Cl₂ / 1.5 h

With indium; di-tert-butyl-diazodicarboxylate; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; 1: Condensation / 2: Mitsunobu reaction / 3: ether cleavage;
DOI:10.1021/ol990320r

Reference yield:

: 1676-81-9
N-benzyloxycarbonyl-L-serine methyl ester

: 288852-12-0
methyl 2-((2S,3S)-2-benzoyloxy-4-hydroxy-3-(N-phenylmethoxycarbonyl)amino)butylpropenoate

Guidance literature:: Multi-step reaction with 6 steps

1: 81 percent / TMSOTf / CH₂Cl₂ / 1.25 h / -78 °C

2: 88 percent / LiBH₄ / methanol; diethyl ether / 0.25 h / Heating

3: 93 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

4: 37 percent / indium / tetrahydrofuran; H₂O / 4.5 h

5: 64 percent / di-tert-butyl azodicarboxylate; Ph₃P / tetrahydrofuran / 20 °C

6: 88 percent / 2,3-dichloro-5,6-dicyanobenzoquinone / H₂O; CH₂Cl₂ / 1.5 h

With indium; lithium borohydride; trimethylsilyl trifluoromethanesulfonate; di-tert-butyl-diazodicarboxylate; Dess-Martin periodane; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; 1: Alkylation / 2: Reduction / 3: Oxidation / 4: Condensation / 5: Mitsunobu reaction / 6: ether cleavage;
DOI:10.1021/ol990320r