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

Base Information

• Chemical Name: <3S-<3α(S^*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-formyl-2-azetidinone
• CAS No.: 92686-05-0
• Molecular Formula: C₂₁H₃₃NO₅Si
• Molecular Weight: 407.582

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

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

Chemical Property:

Purity/Quality:

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

There total 10 articles about <3S-<3α(S^*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-formyl-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: 91.8%

<3S-<3α(S*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-hydroxymethyl-2-azetidinone (81902-62-7) → <3S-<3α(S*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-formyl-2-azetidinone (92686-05-0)

Guidance literature:

With phosphoric acid; In dimethyl sulfoxide; for 18h; Ambient temperature;

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

Reference yield: 60.0%

<3S-<3α(S*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-2-azetidinone-4-carboxylic acid chloride (81902-58-1) → <3S-<3α(S*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-formyl-2-azetidinone (92686-05-0)

Guidance literature:

With bis(triphenylphosphine)copper(I) tetrahydroborate; triphenylphosphine; In acetone; for 1h; Ambient temperature;

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-formyl-2-azetidinone (92686-05-0)

Guidance literature:

Multi-step reaction with 6 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: 91.8 percent / H₃PO₄ / dimethylsulfoxide / 18 h / Ambient temperature

With dmap; lithium aluminium tetrahydride; phosphoric acid; triethylamine; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; In tetrahydrofuran; dimethyl sulfoxide; N,N-dimethyl-formamide;

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

upstream raw materials:

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

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

2,4-dimethoxybenzylamine hydrochloride

<3S-<3α(S^*),4β>>-t-butyl 1-(2,4-dimethoxybenzyl)-3-(1-hydroxyethyl)-2-azetidinone-4-carboxylate

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