3-[3-(allyl-tert-butoxycarbonyl-amino)-2-iodo-phenyl]-2-azido-3-hydroxy-propionic acid methyl ester

Base Information

Chemical Name:3-[3-(allyl-tert-butoxycarbonyl-amino)-2-iodo-phenyl]-2-azido-3-hydroxy-propionic acid methyl ester
CAS No.:204916-05-2
Molecular Formula:C₁₈H₂₃IN₄O₅
Molecular Weight:502.309
Hs Code.:

3-[3-(allyl-<i>tert</i>-butoxycarbonyl-amino)-2-iodo-phenyl]-2-azido-3-hydroxy-propionic acid methyl ester

Synonyms:3-[3-(allyl-tert-butoxycarbonyl-amino)-2-iodo-phenyl]-2-azido-3-hydroxy-propionic acid methyl ester

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Chemical Property of 3-[3-(allyl-tert-butoxycarbonyl-amino)-2-iodo-phenyl]-2-azido-3-hydroxy-propionic acid methyl ester

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Technology Process of 3-[3-(allyl-tert-butoxycarbonyl-amino)-2-iodo-phenyl]-2-azido-3-hydroxy-propionic acid methyl ester

There total 8 articles about 3-[3-(allyl-tert-butoxycarbonyl-amino)-2-iodo-phenyl]-2-azido-3-hydroxy-propionic acid methyl 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: 64.0%

: 1816-92-8
Methyl azidoacetate

: 204916-04-1
3-[N-(tert-butyloxycarbonyl)-N-(2-propenyl)amino]-2-iodobenzaldehyde

: 204916-05-2
3-[3-(allyl-tert-butoxycarbonyl-amino)-2-iodo-phenyl]-2-azido-3-hydroxy-propionic acid methyl ester

Guidance literature:: With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1.75h;
DOI:10.1021/jo990464j

Reference yield:

: 5398-69-6
2-iodo-3-nitrobenzoic acid

: 204916-05-2
3-[3-(allyl-tert-butoxycarbonyl-amino)-2-iodo-phenyl]-2-azido-3-hydroxy-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: B(OME)3 / tetrahydrofuran / 1.5 h / Heating

2: 75.8 g / DMAP; ET₃N / CH₂Cl₂ / 0.17 h / 0 °C

3: 91 percent / Fe; AcOH / aq. ethanol / 0.25 h / Heating

4: 48 percent / dioxane / 48 h / Heating

5: NaH / dimethylformamide / 1 h / 0 - 20 °C

6: aq. K₂CO₃ / methanol / 0.25 h / 20 °C

7: 25.3 g / MnO₂ / ethyl acetate / 32 h / Heating

8: 64 percent / NaHMDS / tetrahydrofuran / 1.75 h / -78 °C

With dmap; manganese(IV) oxide; Trimethyl borate; sodium hexamethyldisilazane; iron; sodium hydride; potassium carbonate; acetic acid; triethylamine; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 1: Reduction / 2: Esterification / 3: Reduction / 4: Acylation / 5: Alkylation / 6: Hydrolysis / 7: Oxidation / 8: Condensation;
DOI:10.1021/jo990464j

Reference yield:

: 158616-08-1
(2-iodo-3-nitrophenyl)methanol

: 204916-05-2
3-[3-(allyl-tert-butoxycarbonyl-amino)-2-iodo-phenyl]-2-azido-3-hydroxy-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 75.8 g / DMAP; ET₃N / CH₂Cl₂ / 0.17 h / 0 °C

2: 91 percent / Fe; AcOH / aq. ethanol / 0.25 h / Heating

3: 48 percent / dioxane / 48 h / Heating

4: NaH / dimethylformamide / 1 h / 0 - 20 °C

5: aq. K₂CO₃ / methanol / 0.25 h / 20 °C

6: 25.3 g / MnO₂ / ethyl acetate / 32 h / Heating

7: 64 percent / NaHMDS / tetrahydrofuran / 1.75 h / -78 °C

With dmap; manganese(IV) oxide; sodium hexamethyldisilazane; iron; sodium hydride; potassium carbonate; acetic acid; triethylamine; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 1: Esterification / 2: Reduction / 3: Acylation / 4: Alkylation / 5: Hydrolysis / 6: Oxidation / 7: Condensation;
DOI:10.1021/jo990464j