benzyl (2R,5S,1'S)-5-{1'-[(tert-butoxycarbonyl)amino]ethyl}tetrahydrofuran-2-carboxylate

Base Information

Chemical Name:benzyl (2R,5S,1'S)-5-{1'-[(tert-butoxycarbonyl)amino]ethyl}tetrahydrofuran-2-carboxylate
CAS No.:259091-46-8
Molecular Formula:C₁₉H₂₇NO₅
Molecular Weight:349.427
Hs Code.:

Synonyms:benzyl (2R,5S,1'S)-5-{1'-[(tert-butoxycarbonyl)amino]ethyl}tetrahydrofuran-2-carboxylate

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Chemical Property of benzyl (2R,5S,1'S)-5-{1'-[(tert-butoxycarbonyl)amino]ethyl}tetrahydrofuran-2-carboxylate

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Technology Process of benzyl (2R,5S,1'S)-5-{1'-[(tert-butoxycarbonyl)amino]ethyl}tetrahydrofuran-2-carboxylate

There total 8 articles about benzyl (2R,5S,1'S)-5-{1'-[(tert-butoxycarbonyl)amino]ethyl}tetrahydrofuran-2-carboxylate 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: 64.0%

: 100-39-0
benzyl bromide

: 259091-45-7
(2R,5S,1'S)-5-{1'-[(tert-butoxycarbonyl)amino]ethyl}tetrahydrofuran-2-carboxylic acid

: 259091-46-8
benzyl (2R,5S,1'S)-5-{1'-[(tert-butoxycarbonyl)amino]ethyl}tetrahydrofuran-2-carboxylate

Guidance literature:: With triethylamine; In acetone; at 0 ℃;
DOI:10.1002/(sici)1099-0690(199911)1999:11<2977::aid-ejoc2977>3.0.co;2-3

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 259091-46-8
benzyl (2R,5S,1'S)-5-{1'-[(tert-butoxycarbonyl)amino]ethyl}tetrahydrofuran-2-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: 1.94 g / NaOH / methanol; H₂O / 0.17 h / 20 °C

2: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / 0.75 h / -60 °C

3: 343 mg / NaH₂PO₄*2H₂O; NaClO₂; amylene / H₂O; 2-methyl-propan-2-ol / 20 °C

4: 64 percent / Et₃N / acetone / 0 °C

With sodium hydroxide; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In methanol; dichloromethane; water; acetone; tert-butyl alcohol; 1: Condensation / 2: Swern oxidation / 3: Oxidation / 4: benzylation;
DOI:10.1002/(sici)1099-0690(199911)1999:11<2977::aid-ejoc2977>3.0.co;2-3

Reference yield:

: [(2R,5S)-5-((S)-1-Amino-ethyl)-tetrahydro-furan-2-yl]-methanol

: 259091-46-8
benzyl (2R,5S,1'S)-5-{1'-[(tert-butoxycarbonyl)amino]ethyl}tetrahydrofuran-2-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: 1.94 g / NaOH / methanol; H₂O / 0.17 h / 20 °C

2: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / 0.75 h / -60 °C

3: 343 mg / NaH₂PO₄*2H₂O; NaClO₂; amylene / H₂O; 2-methyl-propan-2-ol / 20 °C

4: 64 percent / Et₃N / acetone / 0 °C

With sodium hydroxide; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In methanol; dichloromethane; water; acetone; tert-butyl alcohol; 1: Condensation / 2: Swern oxidation / 3: Oxidation / 4: benzylation;
DOI:10.1002/(sici)1099-0690(199911)1999:11<2977::aid-ejoc2977>3.0.co;2-3