methyl 4-<1-(benzyloxy)-2-oxo-4-azetidinyl>-β-<(tert-butyldimethylsilyl)oxy>butyrate

Base Information

Chemical Name:methyl 4-<1-(benzyloxy)-2-oxo-4-azetidinyl>-β-<(tert-butyldimethylsilyl)oxy>butyrate
CAS No.:133374-67-1
Molecular Formula:C₂₁H₃₃NO₅Si
Molecular Weight:407.582
Hs Code.:

Synonyms:methyl 4-<1-(benzyloxy)-2-oxo-4-azetidinyl>-β-<(tert-butyldimethylsilyl)oxy>butyrate

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Chemical Property of methyl 4-<1-(benzyloxy)-2-oxo-4-azetidinyl>-β-<(tert-butyldimethylsilyl)oxy>butyrate

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Technology Process of methyl 4-<1-(benzyloxy)-2-oxo-4-azetidinyl>-β-<(tert-butyldimethylsilyl)oxy>butyrate

There total 6 articles about methyl 4-<1-(benzyloxy)-2-oxo-4-azetidinyl>-β-<(tert-butyldimethylsilyl)oxy>butyrate 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: 66.0%

: 130075-12-6
β-<(tert-butyldimethylsilyl)oxy>-δ-hydroxypimelic acid, N-(benzyloxy)amide monomethyl ester

: 133374-67-1
methyl 4-<1-(benzyloxy)-2-oxo-4-azetidinyl>-β-<(tert-butyldimethylsilyl)oxy>butyrate

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate;
DOI:10.1016/S0040-4039(00)98791-4

Reference yield:

: 622-33-3
N-benzyloxyamine

: 133374-67-1
methyl 4-<1-(benzyloxy)-2-oxo-4-azetidinyl>-β-<(tert-butyldimethylsilyl)oxy>butyrate

Guidance literature:: Multi-step reaction with 2 steps

1: 1) H₂, 2) N-hydroxysuccinimide, dicyclohexylcarbodiimide / 1) 10percent Pd/C

2: 66 percent / Ph₃P, diethyl azodicarboxylate / tetrahydrofuran / 1) 45 min., -10 deg C, 2) 2 h, r.t.

With 1-hydroxy-pyrrolidine-2,5-dione; hydrogen; dicyclohexyl-carbodiimide; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran;
DOI:10.1021/jo00003a066

Reference yield:

: 109462-20-6
1-methyl hydrogen 3-<(tert-butyl)dimethylsilyloxy>glutarate

: 133374-67-1
methyl 4-<1-(benzyloxy)-2-oxo-4-azetidinyl>-β-<(tert-butyldimethylsilyl)oxy>butyrate

Guidance literature:: Multi-step reaction with 4 steps

1: 1) carbonyldiimidazole / 1) THF, 3 h, r.t., 2) a) 42 h, r.t., b) 24 h, 35 deg C

2: 84 percent / NaBH₄ / methanol / 0.25 h / 0 °C

3: 1) H₂, 2) N-hydroxysuccinimide, dicyclohexylcarbodiimide / 1) 10percent Pd/C

4: 66 percent / Ph₃P, diethyl azodicarboxylate / tetrahydrofuran / 1) 45 min., -10 deg C, 2) 2 h, r.t.

With sodium tetrahydroborate; 1-hydroxy-pyrrolidine-2,5-dione; hydrogen; dicyclohexyl-carbodiimide; triphenylphosphine; 1,1'-carbonyldiimidazole; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol;
DOI:10.1021/jo00003a066