methyl (3R,αR)-2-(2-oxo-3-phthalimido-1-azetidinyl)-2-(4-benzyloxyphenyl)acetate

Base Information

Chemical Name:methyl (3R,αR)-2-(2-oxo-3-phthalimido-1-azetidinyl)-2-(4-benzyloxyphenyl)acetate
CAS No.:64232-07-1
Molecular Formula:C₂₇H₂₂N₂O₆
Molecular Weight:470.481
Hs Code.:

Synonyms:methyl (3R,αR)-2-(2-oxo-3-phthalimido-1-azetidinyl)-2-(4-benzyloxyphenyl)acetate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of methyl (3R,αR)-2-(2-oxo-3-phthalimido-1-azetidinyl)-2-(4-benzyloxyphenyl)acetate

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Technology Process of methyl (3R,αR)-2-(2-oxo-3-phthalimido-1-azetidinyl)-2-(4-benzyloxyphenyl)acetate

There total 12 articles about methyl (3R,αR)-2-(2-oxo-3-phthalimido-1-azetidinyl)-2-(4-benzyloxyphenyl)acetate 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: 93.0%

: 78246-50-1
methyl (L)-N^α-phthaloylseryl-(D)-p-benzyloxyphenylglycinate

: 64232-07-1,64253-60-7,68749-65-5,78246-51-2
(4-Benzyloxy-phenyl)-[(S)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-oxo-azetidin-1-yl]-acetic acid methyl ester

Guidance literature:: With thiamine diphosphate; diethylazodicarboxylate; with 1 equiv of reagents;
DOI:10.1016/S0040-4020(01)92149-0

Reference yield: 40.4%

: 6780-38-7
N-phthaloylglycine chloride

: 63856-16-6
trimethyl <αR,α'R,α''R>-α,α',α''-tri(4-benzyloxyphenyl)hexahydro-1,3,5-triazine-1,3,5-triacetate

: 64232-07-1
methyl (3R,αR)-2-(2-oxo-3-phthalimido-1-azetidinyl)-2-(4-benzyloxyphenyl)acetate

: 64253-60-7
methyl (3S,αR)-2-(2-oxo-3-phthalimido-1-azetidinyl)-2-(4-benzyloxyphenyl)acetate

Guidance literature:: With boron trifluoride diethyl etherate; Yields of byproduct given; 1.) pyridine, CH₂Cl₂, -78 deg C, 2 h; 2.) 1 h, 0 deg C;
DOI:10.1248/cpb.35.3985

Reference yield:

: 29588-89-4
N-phthaloyl-L-serine

: 64232-07-1,64253-60-7,68749-65-5,78246-51-2
(4-Benzyloxy-phenyl)-[(S)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-oxo-azetidin-1-yl]-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) 1-hydroxybenzotriazole hydrate, 2.) dicyclohexylcarbodiimide / 1.) DMF, 0 deg C, 15 min, 2.) 0 deg C (1 h) , room temperature, 1 h

2: triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / Ambient temperature; influence of reagents amount

With 1-hydroxybenzotriazol-hydrate; dicyclohexyl-carbodiimide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran;
DOI:10.1021/ja00342a047