Methyl (2R,3S,4S,5S)-2-benzyl-5-[(tert-butoxycarbonyl)amino]-3,4-epoxy-6-phenylhexanoate

Base Information

Chemical Name:Methyl (2R,3S,4S,5S)-2-benzyl-5-[(tert-butoxycarbonyl)amino]-3,4-epoxy-6-phenylhexanoate
CAS No.:155158-46-6
Molecular Formula:C₂₅H₃₁NO₅
Molecular Weight:425.525
Hs Code.:

Synonyms:Methyl (2R,3S,4S,5S)-2-benzyl-5-[(tert-butoxycarbonyl)amino]-3,4-epoxy-6-phenylhexanoate

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Chemical Property of Methyl (2R,3S,4S,5S)-2-benzyl-5-[(tert-butoxycarbonyl)amino]-3,4-epoxy-6-phenylhexanoate

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Technology Process of Methyl (2R,3S,4S,5S)-2-benzyl-5-[(tert-butoxycarbonyl)amino]-3,4-epoxy-6-phenylhexanoate

There total 9 articles about Methyl (2R,3S,4S,5S)-2-benzyl-5-[(tert-butoxycarbonyl)amino]-3,4-epoxy-6-phenylhexanoate 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: 25.0%

: 137278-30-9
methyl (2R,5S)-2-benzyl-5-t-butoxycarbonylamino-6-phenyl-E-3-hexenoate

: Methyl (2R,3R,4R,5S)-2-benzyl-5-[(tert-butoxycarbonyl)amino]-3,4-epoxy-6-phenylhexanoate

: 155158-46-6
Methyl (2R,3S,4S,5S)-2-benzyl-5-[(tert-butoxycarbonyl)amino]-3,4-epoxy-6-phenylhexanoate

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 40h; Ambient temperature;
DOI:10.1021/jo00084a037

Reference yield:

: 2612-30-8
2-benzyl-1,3-propanediol

: 155158-46-6
Methyl (2R,3S,4S,5S)-2-benzyl-5-[(tert-butoxycarbonyl)amino]-3,4-epoxy-6-phenylhexanoate

Guidance literature:: Multi-step reaction with 6 steps

1: triethylamine / CH₂Cl₂ / Ambient temperature

2: DMSO, oxalyl chloride, diisopropylethylamine / CH₂Cl₂ / -78 deg C, 30 min then warm to room temp.

4: 74 percent / Jones' reagent / acetone / 0.5 h / 0 °C

5: 87 percent / diethyl ether / Ambient temperature

6: 25 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 40 h / Ambient temperature

With jones' reagent; oxalyl dichloride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In diethyl ether; dichloromethane; acetone;
DOI:10.1021/jo00084a037

Reference yield:

: 49769-78-0
2-benzyl-malonic acid dimethyl ester

: 155158-46-6
Methyl (2R,3S,4S,5S)-2-benzyl-5-[(tert-butoxycarbonyl)amino]-3,4-epoxy-6-phenylhexanoate

Guidance literature:: Multi-step reaction with 7 steps

1: 100 percent / LiAlH₄ / diethyl ether / Ambient temperature

2: triethylamine / CH₂Cl₂ / Ambient temperature

3: DMSO, oxalyl chloride, diisopropylethylamine / CH₂Cl₂ / -78 deg C, 30 min then warm to room temp.

5: 74 percent / Jones' reagent / acetone / 0.5 h / 0 °C

6: 87 percent / diethyl ether / Ambient temperature

7: 25 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 40 h / Ambient temperature

With lithium aluminium tetrahydride; jones' reagent; oxalyl dichloride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In diethyl ether; dichloromethane; acetone;
DOI:10.1021/jo00084a037