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

Base Information

• Chemical Name: <3S-<3α(S^*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-methanesulfonyloxymethyl-2-azetidinone
• CAS No.: 92685-99-9
• Molecular Formula: C₂₂H₃₇NO₇SSi
• Molecular Weight: 487.69

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

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

Chemical Property:

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

There total 9 articles about <3S-<3α(S^*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-methanesulfonyloxymethyl-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: 98.0%

<3S-<3α(S*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-hydroxymethyl-2-azetidinone (81902-62-7) + methanesulfonyl chloride (124-63-0) → <3S-<3α(S*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-methanesulfonyloxymethyl-2-azetidinone (92685-99-9)

Guidance literature:

With triethylamine; In tetrahydrofuran; 1.) 5 deg C, 2.) room temp, 1 h.;

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-methanesulfonyloxymethyl-2-azetidinone (92685-99-9)

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

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

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-methanesulfonyloxymethyl-2-azetidinone (92685-99-9)

Guidance literature:

Multi-step reaction with 4 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.

With dmap; lithium aluminium tetrahydride; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; 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

methanesulfonyl chloride

2,4-dimethoxybenzylamine hydrochloride

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

Downstream raw materials:

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

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

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