(S)-2-[(1R,2R)-2-Acetoxy-1-(tert-butyl-dimethyl-silanyloxy)-but-3-enyl]-aziridine-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: (S)-2-[(1R,2R)-2-Acetoxy-1-(tert-butyl-dimethyl-silanyloxy)-but-3-enyl]-aziridine-1-carboxylic acid benzyl ester
• CAS No.: 144001-84-3
• Molecular Formula: C₂₂H₃₃NO₅Si
• Molecular Weight: 419.593

Synonyms:(S)-2-[(1R,2R)-2-Acetoxy-1-(tert-butyl-dimethyl-silanyloxy)-but-3-enyl]-aziridine-1-carboxylic acid benzyl ester

Chemical Property of (S)-2-[(1R,2R)-2-Acetoxy-1-(tert-butyl-dimethyl-silanyloxy)-but-3-enyl]-aziridine-1-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

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Technology Process of (S)-2-[(1R,2R)-2-Acetoxy-1-(tert-butyl-dimethyl-silanyloxy)-but-3-enyl]-aziridine-1-carboxylic acid benzyl ester

There total 10 articles about (S)-2-[(1R,2R)-2-Acetoxy-1-(tert-butyl-dimethyl-silanyloxy)-but-3-enyl]-aziridine-1-carboxylic acid benzyl ester 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: 85.0%

Acetic acid (1R,2R,3S)-3-benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-1-vinyl-butyl ester (144001-83-2) → (S)-2-[(1R,2R)-2-Acetoxy-1-(tert-butyl-dimethyl-silanyloxy)-but-3-enyl]-aziridine-1-carboxylic acid benzyl ester (144001-84-3)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 23 ℃; for 12h;

DOI:10.1021/jo00048a006

Reference yield:

(+)-D-glucosamine hydrochloride (1078691-95-8) → (S)-2-[(1R,2R)-2-Acetoxy-1-(tert-butyl-dimethyl-silanyloxy)-but-3-enyl]-aziridine-1-carboxylic acid benzyl ester (144001-84-3)

Guidance literature:

Multi-step reaction with 10 steps

1: NaHCO₃ / dioxane; H₂O / 24 °C

2: HCl / 24 h / Heating

3: CSA / dimethylformamide / 80 °C

4: 90 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

5: 73 percent / (NH₄)2Ce(NO₃)6 / acetonitrile; H₂O / 1 h / 25 °C

6: 88 percent / iodine, Ph₃P, pyridine / toluene / 70 °C

7: 98 percent / pyridine, DMAP / CH₂Cl₂ / 24 °C

8: activated Zn, 95 percent EtOH / 1 h / 78 °C

9: NaBH₄ / tetrahydrofuran; H₂O / -43 °C

10: 85 percent / Ph₃P, diethyl azodicarboxylate / tetrahydrofuran / 12 h / 23 °C

With pyridine; 2,6-dimethylpyridine; hydrogenchloride; dmap; sodium tetrahydroborate; ammonium cerium(IV) nitrate; ethanol; camphor-10-sulfonic acid; iodine; sodium hydrogencarbonate; triphenylphosphine; zinc; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/jo00048a006

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → (S)-2-[(1R,2R)-2-Acetoxy-1-(tert-butyl-dimethyl-silanyloxy)-but-3-enyl]-aziridine-1-carboxylic acid benzyl ester (144001-84-3)

Guidance literature:

Multi-step reaction with 10 steps

1: NaHCO₃ / dioxane; H₂O / 24 °C

2: HCl / 24 h / Heating

3: CSA / dimethylformamide / 80 °C

4: 90 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

5: 73 percent / (NH₄)2Ce(NO₃)6 / acetonitrile; H₂O / 1 h / 25 °C

6: 88 percent / iodine, Ph₃P, pyridine / toluene / 70 °C

7: 98 percent / pyridine, DMAP / CH₂Cl₂ / 24 °C

8: activated Zn, 95 percent EtOH / 1 h / 78 °C

9: NaBH₄ / tetrahydrofuran; H₂O / -43 °C

10: 85 percent / Ph₃P, diethyl azodicarboxylate / tetrahydrofuran / 12 h / 23 °C

With pyridine; 2,6-dimethylpyridine; hydrogenchloride; dmap; sodium tetrahydroborate; ammonium cerium(IV) nitrate; ethanol; camphor-10-sulfonic acid; iodine; sodium hydrogencarbonate; triphenylphosphine; zinc; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/jo00048a006

upstream raw materials:

Acetic acid (1R,2R,3S)-3-benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-1-vinyl-butyl ester

2-carbobenzyloxyamino-2-deoxy-D-glucopyranose

(+)-D-glucosamine hydrochloride

benzyl chloroformate

Downstream raw materials:

(S)-2-[(1R,2S)-2-Acetoxy-1-(tert-butyl-dimethyl-silanyloxy)-3-oxo-propyl]-aziridine-1-carboxylic acid benzyl ester

(4R,5R) methyl 4-acetoxy-5-[(tert-butyldimethylsilyl)oxy]-5-[(2S)-N-(benzoxycarbonyl)aziridin-2-yl]-3-bromo-2-[N-(methoxycarbonyl)imino]pentanoate

(S)-2-{(R)-2-Acetoxy-3,3-dibromo-1-(tert-butyl-dimethyl-silanyloxy)-4-methoxycarbonyl-4-[(E)-methoxycarbonylimino]-butyl}-aziridine-1-carboxylic acid benzyl ester

(S)-2-[(E)-(1R,2R)-2-Acetoxy-1-(tert-butyl-dimethyl-silanyloxy)-4-methoxycarbonyl-4-methoxycarbonylamino-but-3-enyl]-aziridine-1-carboxylic acid benzyl ester

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