4-nitrobenzyl (2R*,3S*)-1-tert-butyldimethylsilyl-3-<(R*)-1-tert-butyldimethylsilyloxyethyl>-4-oxo-2-azetidine-α-butynoate

Base Information

• Chemical Name: 4-nitrobenzyl (2R*,3S*)-1-tert-butyldimethylsilyl-3-<(R*)-1-tert-butyldimethylsilyloxyethyl>-4-oxo-2-azetidine-α-butynoate
• CAS No.: 83641-62-7
• Molecular Formula: C₂₈H₄₄N₂O₆Si₂
• Molecular Weight: 560.838

Synonyms:4-nitrobenzyl (2R*,3S*)-1-tert-butyldimethylsilyl-3-<(R*)-1-tert-butyldimethylsilyloxyethyl>-4-oxo-2-azetidine-α-butynoate

Chemical Property of 4-nitrobenzyl (2R*,3S*)-1-tert-butyldimethylsilyl-3-<(R*)-1-tert-butyldimethylsilyloxyethyl>-4-oxo-2-azetidine-α-butynoate

Chemical Property:

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Technology Process of 4-nitrobenzyl (2R*,3S*)-1-tert-butyldimethylsilyl-3-<(R*)-1-tert-butyldimethylsilyloxyethyl>-4-oxo-2-azetidine-α-butynoate

There total 2 articles about 4-nitrobenzyl (2R*,3S*)-1-tert-butyldimethylsilyl-3-<(R*)-1-tert-butyldimethylsilyloxyethyl>-4-oxo-2-azetidine-α-butynoate 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:

(3S*,4R*)-1-tert-butyldimethylsilyl-3-<(R*)-1-tert-butyldimethylsilyloxyethyl>-4-(2-propynyllithium)-2-azetidinone (83641-61-6) + 4-nitrobenzyl chloroformate (4457-32-3) → 4-nitrobenzyl (2R*,3S*)-1-tert-butyldimethylsilyl-3-<(R*)-1-tert-butyldimethylsilyloxyethyl>-4-oxo-2-azetidine-α-butynoate (83641-62-7) + (3S*,4R*)-1-tert-butyldimethylsilyl-3-<(R*)-1-tert-butyldimethylsilyloxyethyl>-4-(2-propynyl)-2-azetidinone (83641-60-5,85281-81-8,88823-92-1)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.5h;

DOI:10.1248/cpb.34.1434

Reference yield:

4-nitrobenzyl chloroformate (4457-32-3) → 4-nitrobenzyl (2R*,3S*)-1-tert-butyldimethylsilyl-3-<(R*)-1-tert-butyldimethylsilyloxyethyl>-4-oxo-2-azetidine-α-butynoate (83641-62-7) + (3S*,4R*)-1-tert-butyldimethylsilyl-3-<(R*)-1-tert-butyldimethylsilyloxyethyl>-4-(2-propynyl)-2-azetidinone (83641-60-5,85281-81-8,88823-92-1)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/S0040-4039(00)88437-3

Reference yield:

4-nitrobenzyl (2R*,3S*)-1-tert-butyldimethylsilyl-3-<(R*)-1-tert-butyldimethylsilyloxyethyl>-4-oxo-2-azetidine-α-butynoate (83641-62-7) → 4-nitrobenzyl (2R*,3S*)-1-tert-butyldimethylsilyl-3-<(R*)-1-tert-butyldimethylsilyloxyethyl>-4,β-dioxo-2-azetidinebutyrate (74288-37-2,77171-44-9,79617-32-6,88823-87-4)

Guidance literature:

Multistep reaction;

DOI:10.1016/S0040-4039(00)88437-3

upstream raw materials:

4-nitrobenzyl chloroformate

(3S*,4R*)-1-tert-butyldimethylsilyl-3-<(R*)-1-tert-butyldimethylsilyloxyethyl>-4-(2-propynyllithium)-2-azetidinone

Downstream raw materials:

4-nitrobenzyl (2R*,3S*)-1-tert-butyldimethylsilyl-3-<(R*)-1-tert-butyldimethylsilyloxyethyl>-4,β-dioxo-2-azetidinebutyrate

(Z)-4-{(2R,3S)-1-(tert-Butyl-dimethyl-silanyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-3-phenylsulfanyl-but-2-enoic acid 4-nitro-benzyl ester

(Z)-4-{(2R,3S)-1-(tert-Butyl-dimethyl-silanyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-3-phenylsulfanyl-but-2-enoic acid 4-nitro-benzyl ester

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