<3S-<3α(S^*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-cyanomethyl-2-azetidinone

Base Information

• Chemical Name: <3S-<3α(S^*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-cyanomethyl-2-azetidinone
• CAS No.: 92686-01-6
• Molecular Formula: C₂₂H₃₄N₂O₄Si
• Molecular Weight: 418.608

Synonyms:<3S-<3α(S^*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-cyanomethyl-2-azetidinone

Chemical Property of <3S-<3α(S^*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-cyanomethyl-2-azetidinone

Chemical Property:

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Technology Process of <3S-<3α(S^*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-cyanomethyl-2-azetidinone

There total 11 articles about <3S-<3α(S^*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-cyanomethyl-2-azetidinone 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%

potassium cyanide (151-50-8) + <3S-<3α(S*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-iodomethyl-2-azetidinone (92686-00-5) → <3S-<3α(S*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-cyanomethyl-2-azetidinone (92686-01-6)

Guidance literature:

In N,N-dimethyl-formamide; at 50 ℃; for 15h;

DOI:10.1016/S0040-4020(01)91132-9

Reference yield:

2,4-dimethoxybenzylamine hydrochloride (20781-21-9) → <3S-<3α(S*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-cyanomethyl-2-azetidinone (92686-01-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 58 percent / Et₃N / tetrahydrofuran / 1 h / Heating

2: 84 percent / N,N-dicyclohexylcarbodiimide / tetrahydrofuran / 0.25 h / 20 - 25 °C

3: 1.) LiN(SiMe₃)2, 2.) LiN(SiMe₃)2 / 1.) THF, 15 min., from 0 deg C to 5 deg C, 2.) from 20 deg C to 25 deg C, THF, 1 h.

4: 96.7 percent / 4-dimethylaminopyridine / dimethylformamide / Ambient temperature

5: 50 percent / LiAlH₄ / tetrahydrofuran / 0.75 h / 5 °C

6: 98 percent / Et₃N / tetrahydrofuran / 1.) 5 deg C, 2.) room temp, 1 h.

7: 82 percent / NaI / acetone / 18 h / Heating

8: 93 percent / dimethylformamide / 15 h / 50 °C

With dmap; lithium aluminium tetrahydride; triethylamine; dicyclohexyl-carbodiimide; sodium iodide; lithium hexamethyldisilazane; In tetrahydrofuran; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4020(01)91132-9

Reference yield:

(2S,3R)-N-(2,4-dimethoxybenzyl)-N-(t-butoxycarbonylmethyl)-2-bromo-3-hydroxybutyramide (81902-59-2) → <3S-<3α(S*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-cyanomethyl-2-azetidinone (92686-01-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) LiN(SiMe₃)2, 2.) LiN(SiMe₃)2 / 1.) THF, 15 min., from 0 deg C to 5 deg C, 2.) from 20 deg C to 25 deg C, THF, 1 h.

2: 96.7 percent / 4-dimethylaminopyridine / dimethylformamide / Ambient temperature

3: 50 percent / LiAlH₄ / tetrahydrofuran / 0.75 h / 5 °C

4: 98 percent / Et₃N / tetrahydrofuran / 1.) 5 deg C, 2.) room temp, 1 h.

5: 82 percent / NaI / acetone / 18 h / Heating

6: 93 percent / dimethylformamide / 15 h / 50 °C

With dmap; lithium aluminium tetrahydride; triethylamine; sodium iodide; lithium hexamethyldisilazane; In tetrahydrofuran; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4020(01)91132-9

upstream raw materials:

potassium cyanide

<3S-<3α(S^*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-iodomethyl-2-azetidinone

2,4-dimethoxybenzylamine hydrochloride

<3S-<3α(S^*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-hydroxymethyl-2-azetidinone

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