(1S,4S,5S)-4-O-benzyl-1-{N-[(tert-butyloxycarbonyl)amino]methyl}tetrahydropyran-6-N-L-methionine methyl ester

Base Information

Chemical Name:(1S,4S,5S)-4-O-benzyl-1-{N-[(tert-butyloxycarbonyl)amino]methyl}tetrahydropyran-6-N-L-methionine methyl ester
CAS No.:742102-84-7
Molecular Formula:C₂₅H₄₀N₂O₆S
Molecular Weight:496.668
Hs Code.:

Synonyms:(1S,4S,5S)-4-O-benzyl-1-{N-[(tert-butyloxycarbonyl)amino]methyl}tetrahydropyran-6-N-L-methionine methyl ester

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Chemical Property of (1S,4S,5S)-4-O-benzyl-1-{N-[(tert-butyloxycarbonyl)amino]methyl}tetrahydropyran-6-N-L-methionine methyl ester

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Technology Process of (1S,4S,5S)-4-O-benzyl-1-{N-[(tert-butyloxycarbonyl)amino]methyl}tetrahydropyran-6-N-L-methionine methyl ester

There total 9 articles about (1S,4S,5S)-4-O-benzyl-1-{N-[(tert-butyloxycarbonyl)amino]methyl}tetrahydropyran-6-N-L-methionine methyl ester 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:

: (S)-2-[[(2R,3S,6S)-3-Benzyloxy-6-(tert-butoxycarbonylamino-methyl)-tetrahydro-pyran-2-ylmethyl]-(2-nitro-benzenesulfonyl)-amino]-4-methylsulfanyl-butyric acid methyl ester

: 742102-84-7
(1S,4S,5S)-4-O-benzyl-1-{N-[(tert-butyloxycarbonyl)amino]methyl}tetrahydropyran-6-N-L-methionine methyl ester

Guidance literature:: With potassium carbonate; thiophenol; In acetonitrile; at 50 ℃;
DOI:10.1021/jm049927q

Reference yield:

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

: 742102-84-7
(1S,4S,5S)-4-O-benzyl-1-{N-[(tert-butyloxycarbonyl)amino]methyl}tetrahydropyran-6-N-L-methionine methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: Et₃N / CH₂Cl₂

2: 4.16 g / NaOMe / methanol

3: 71 percent / (+)-camphorsulfonic acid / acetonitrile / 2 h / 65 °C

4: 70 percent / DIBAL-H / toluene / 0.5 h / 0 °C

5: PPh₃; diethyl azodicarboxylate / tetrahydrofuran / 0 °C

6: 196 mg / K₂CO₃; PhSH / acetonitrile / 50 °C

With sodium methylate; diisobutylaluminium hydride; potassium carbonate; thiophenol; (+)-10-camphorsulfonic acid; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; toluene; acetonitrile;
DOI:10.1021/jm049927q

Reference yield:

: 229473-27-2
2,3-dideoxy-1-{N-[(tert-butyloxycarbonyl)amino]methyl}-α-D-glucopyranose

: 742102-84-7
(1S,4S,5S)-4-O-benzyl-1-{N-[(tert-butyloxycarbonyl)amino]methyl}tetrahydropyran-6-N-L-methionine methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 71 percent / (+)-camphorsulfonic acid / acetonitrile / 2 h / 65 °C

2: 70 percent / DIBAL-H / toluene / 0.5 h / 0 °C

3: PPh₃; diethyl azodicarboxylate / tetrahydrofuran / 0 °C

4: 196 mg / K₂CO₃; PhSH / acetonitrile / 50 °C

With diisobutylaluminium hydride; potassium carbonate; thiophenol; (+)-10-camphorsulfonic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene; acetonitrile;
DOI:10.1021/jm049927q