(3R)-3-benzyl-3-tert-butoxycarbonylamino-1-carboxymethyl-azetidin-2-one

Base Information

Chemical Name:(3R)-3-benzyl-3-tert-butoxycarbonylamino-1-carboxymethyl-azetidin-2-one
CAS No.:254112-87-3
Molecular Formula:C₁₇H₂₂N₂O₅
Molecular Weight:334.372
Hs Code.:

Synonyms:(3R)-3-benzyl-3-tert-butoxycarbonylamino-1-carboxymethyl-azetidin-2-one

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Chemical Property of (3R)-3-benzyl-3-tert-butoxycarbonylamino-1-carboxymethyl-azetidin-2-one

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Technology Process of (3R)-3-benzyl-3-tert-butoxycarbonylamino-1-carboxymethyl-azetidin-2-one

There total 6 articles about (3R)-3-benzyl-3-tert-butoxycarbonylamino-1-carboxymethyl-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: 64.0%

: 124-38-9,18923-20-1
carbon dioxide

: 301161-15-9
(3R)-3-benzyl-1-bis(trimethylsilyl)methyl-3-(tert-butoxycarbonylamino)azetidin-2-one

: 254112-87-3
(3R)-3-benzyl-3-tert-butoxycarbonylamino-1-carboxymethyl-azetidin-2-one

Guidance literature:: (3R)-3-benzyl-1-bis(trimethylsilyl)methyl-3-(tert-butoxycarbonylamino)azetidin-2-one; With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In tetrahydrofuran; at -100 ℃; for 0.5h;

carbon dioxide; In tetrahydrofuran; at 20 ℃;
DOI:10.1021/jo060537g

Reference yield:

: 100-39-0
benzyl bromide

: 254112-87-3
(3R)-3-benzyl-3-tert-butoxycarbonylamino-1-carboxymethyl-azetidin-2-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: LDA / tetrahydrofuran / -78 °C

1.2: 90 percent / tetrahydrofuran / -78 - 20 °C

2.1: Li; NH₃ / tetrahydrofuran

2.2: tetrahydrofuran

3.1: (NH₄)2Ce(NO₃)6; NaHCO₃

4.1: Cs₂CO₃

5.1: H₂ / Pd/C

With ammonium cerium(IV) nitrate; ammonia; hydrogen; lithium; sodium hydrogencarbonate; caesium carbonate; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; 1.1: Metallation / 1.2: Alkylation / 2.1: Reduction / 2.2: Acylation / 3.1: dealkylation / 4.1: Alkylation / 5.1: Hydrogenolysis;
DOI:10.1002/(SICI)1521-3773(19991018)38:20<3056::AID-ANIE3056>3.0.CO;2-J

Reference yield:

: 254112-83-9
(3R)-3-benzyl-1-bis(trimethylsilyl)methyl-3-[(4S)-2-oxo-4-phenyloxazolidin-3-yl]azetidin-2-one

: 254112-87-3
(3R)-3-benzyl-3-tert-butoxycarbonylamino-1-carboxymethyl-azetidin-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: Li; NH₃ / tetrahydrofuran

1.2: tetrahydrofuran

2.1: (NH₄)2Ce(NO₃)6; NaHCO₃

3.1: Cs₂CO₃

4.1: H₂ / Pd/C

With ammonium cerium(IV) nitrate; ammonia; hydrogen; lithium; sodium hydrogencarbonate; caesium carbonate; palladium on activated charcoal; In tetrahydrofuran; 1.1: Reduction / 1.2: Acylation / 2.1: dealkylation / 3.1: Alkylation / 4.1: Hydrogenolysis;
DOI:10.1002/(SICI)1521-3773(19991018)38:20<3056::AID-ANIE3056>3.0.CO;2-J