(3S,4S)-1-(p-methoxybenzyl)-3-benzyloxycarbonylamino-4-<(1'R)-1'-methoxyethyl>azetidin-2-one

Base Information

Chemical Name:(3S,4S)-1-(p-methoxybenzyl)-3-benzyloxycarbonylamino-4-<(1'R)-1'-methoxyethyl>azetidin-2-one
CAS No.:112318-30-6
Molecular Formula:C₂₂H₂₆N₂O₅
Molecular Weight:398.459
Hs Code.:

Synonyms:(3S,4S)-1-(p-methoxybenzyl)-3-benzyloxycarbonylamino-4-<(1'R)-1'-methoxyethyl>azetidin-2-one

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Chemical Property of (3S,4S)-1-(p-methoxybenzyl)-3-benzyloxycarbonylamino-4-<(1'R)-1'-methoxyethyl>azetidin-2-one

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Technology Process of (3S,4S)-1-(p-methoxybenzyl)-3-benzyloxycarbonylamino-4-<(1'R)-1'-methoxyethyl>azetidin-2-one

There total 7 articles about (3S,4S)-1-(p-methoxybenzyl)-3-benzyloxycarbonylamino-4-<(1'R)-1'-methoxyethyl>azetidin-2-one 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: 96.0%

: 501-53-1,94274-21-2
benzyl chloroformate

: 112318-28-2
(3S,4S)-1-(p-methoxybenzyl)-3-amino-4-<(1'R)-1'-methoxyethyl>azetidin-2-one

: 112318-30-6
(3S,4S)-1-(p-methoxybenzyl)-3-benzyloxycarbonylamino-4-<(1'R)-1'-methoxyethyl>azetidin-2-one

Guidance literature:: With sodium hydrogencarbonate; In tetrahydrofuran; water; at 0 ℃; for 2h;
DOI:10.1248/cpb.34.2732

Reference yield:

: 112162-27-3
(S)-1-(4-Methoxy-benzyl)-4-oxo-azetidine-2-carbaldehyde

: 112318-30-6
(3S,4S)-1-(p-methoxybenzyl)-3-benzyloxycarbonylamino-4-<(1'R)-1'-methoxyethyl>azetidin-2-one

Guidance literature:: Multi-step reaction with 5 steps

1: 32 percent / diethyl ether / 2.5 h / 0 °C

2: 80 percent / NaH / tetrahydrofuran / 6 h / Ambient temperature

3: 1.) lithium hexamethyldisilazide, 2.) isoamyl nitrite / 1.) THF, -78 deg C, 10 min then -50 deg C, 10 min, 2.) THF, -50 deg C, 1 h

4: 71 percent / hydrogen / PtO₂ / ethyl acetate / 12 h

5: 96 percent / NaHCO₃ / tetrahydrofuran; H₂O / 2 h / 0 °C

With hydrogen; sodium hydride; sodium hydrogencarbonate; lithium hexamethyldisilazane; isopentyl nitrite; platinum(IV) oxide; In tetrahydrofuran; diethyl ether; water; ethyl acetate;
DOI:10.1248/cpb.34.2732

Reference yield:

: 112162-26-2
(4S)-1-(p-methoxybenzyl)-4-hydroxymethylazetidin-2-one

: 112318-30-6
(3S,4S)-1-(p-methoxybenzyl)-3-benzyloxycarbonylamino-4-<(1'R)-1'-methoxyethyl>azetidin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: 682 mg / DMSO, oxalyl chloride / CH₂Cl₂ / 0.25 h / -70 °C

2: 32 percent / diethyl ether / 2.5 h / 0 °C

3: 80 percent / NaH / tetrahydrofuran / 6 h / Ambient temperature

4: 1.) lithium hexamethyldisilazide, 2.) isoamyl nitrite / 1.) THF, -78 deg C, 10 min then -50 deg C, 10 min, 2.) THF, -50 deg C, 1 h

5: 71 percent / hydrogen / PtO₂ / ethyl acetate / 12 h

6: 96 percent / NaHCO₃ / tetrahydrofuran; H₂O / 2 h / 0 °C

With oxalyl dichloride; hydrogen; sodium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; lithium hexamethyldisilazane; isopentyl nitrite; platinum(IV) oxide; In tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate;
DOI:10.1248/cpb.34.2732