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

Base Information

• Chemical Name: <3S-<3α(S^*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-diazoacetyl-2-azetidinone
• CAS No.: 81902-64-9
• Molecular Formula: C₂₂H₃₃N₃O₅Si
• Molecular Weight: 447.607

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

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

Chemical Property:

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

There total 14 articles about <3S-<3α(S^*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-diazoacetyl-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: 73.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + <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-diazoacetyl-2-azetidinone (81902-64-9)

Guidance literature:

In diethyl ether;

DOI:10.1016/S0040-4039(01)92460-8

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-diazoacetyl-2-azetidinone (81902-64-9)

Guidance literature:

Multi-step reaction with 5 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: 18.9 percent / NaBH₄ / ethanol / 18 h / 70 °C

4: 2.1 g / oxalyl chloride / tetrahydrofuran / 2 h / 25 °C

5: tetrahydrofuran / 0.5 h / 0 - 5 °C

With dmap; sodium tetrahydroborate; oxalyl dichloride; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide;

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

Reference yield:

<3S-<3α(S*),4β>>-t-butyl 1-(2,4-dimethoxybenzyl)-3-(1-hydroxyethyl)-2-azetidinone-4-carboxylate (80829-72-7) → <3S-<3α(S*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-diazoacetyl-2-azetidinone (81902-64-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 96.7 percent / 4-dimethylaminopyridine / dimethylformamide / Ambient temperature

2: 18.9 percent / NaBH₄ / ethanol / 18 h / 70 °C

3: 2.1 g / oxalyl chloride / tetrahydrofuran / 2 h / 25 °C

4: tetrahydrofuran / 0.5 h / 0 - 5 °C

With dmap; sodium tetrahydroborate; oxalyl dichloride; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide;

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

upstream raw materials:

diazomethane

<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

Downstream raw materials:

<3S-<3α(S^*),4β>>-benzyl<3-(1-t-butyldimethylsilyloxyethyl)-2-azetidinone-4-yl>acetate

[(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1-(2,4-dimethoxy-benzyl)-4-oxo-azetidin-2-yl]-acetyl chloride

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

(3S,4R)-3-<(R)-1-hydroxyethyl>-4-<(benzyloxycarbonyl)methyl>-2-azetidinone

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