diethyl [(4-{(2S)-2-[(tert-butoxycarbonyl)amino]-3-hydroxypropyl}phenyl)methyl]phosphonate

Base Information

Chemical Name:diethyl [(4-{(2S)-2-[(tert-butoxycarbonyl)amino]-3-hydroxypropyl}phenyl)methyl]phosphonate
CAS No.:213127-96-9
Molecular Formula:C₁₉H₃₂NO₆P
Molecular Weight:401.44
Hs Code.:

Synonyms:diethyl [(4-{(2S)-2-[(tert-butoxycarbonyl)amino]-3-hydroxypropyl}phenyl)methyl]phosphonate

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Chemical Property of diethyl [(4-{(2S)-2-[(tert-butoxycarbonyl)amino]-3-hydroxypropyl}phenyl)methyl]phosphonate

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Technology Process of diethyl [(4-{(2S)-2-[(tert-butoxycarbonyl)amino]-3-hydroxypropyl}phenyl)methyl]phosphonate

There total 9 articles about diethyl [(4-{(2S)-2-[(tert-butoxycarbonyl)amino]-3-hydroxypropyl}phenyl)methyl]phosphonate 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: 77.0%

: 213127-94-7
(2S)-2-[(tert-butoxycarbonyl)amino]-3-{4-[(diethoxyphosphoryl)methyl]phenyl}propyl acetate

: 213127-96-9
diethyl [(4-{(2S)-2-[(tert-butoxycarbonyl)amino]-3-hydroxypropyl}phenyl)methyl]phosphonate

Guidance literature:: With methanol; potassium carbonate; for 1h;
DOI:10.1016/S0040-4020(98)00586-9

Reference yield:

: 108228-81-5
4-(diethoxyphosphorylmethyl)-1-bromomethyl-phenyl

: 213127-96-9
diethyl [(4-{(2S)-2-[(tert-butoxycarbonyl)amino]-3-hydroxypropyl}phenyl)methyl]phosphonate

Guidance literature:: Multi-step reaction with 7 steps

1: 76 percent / NaH / tetrahydrofuran / 0.5 h / 20 °C

2: 79 percent / NaBH₄ / methanol / 2 h / 20 °C

3: 97 percent / lipase PS / tetrahydrofuran / 2 h / 25 °C / Enzymatic reaction; 2 equiv. vinyl acetate

4: Jones reagent / acetone / 4 h / 20 °C

5: 52 percent / diphenylphosphoryl azide; triethylamine / benzene / 24 h / Heating

6: 88 percent / H₂ / Pd-C / ethyl acetate / 12 h / 20 °C / 760 Torr

7: 77 percent / aq. MeOH; K₂CO₃ / 1 h

With methanol; sodium tetrahydroborate; jones reagent; Lipase PS; diphenylphosphoranyl azide; hydrogen; sodium hydride; potassium carbonate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethyl acetate; acetone; benzene; 1: Substitution / 2: Reduction / 3: Acetylation / 4: Oxidation / 5: Rearrangement / 6: Substitution / 7: Hydrolysis;
DOI:10.1016/S0040-4020(98)00586-9

Reference yield:

: 3762-25-2
diethyl 4-methylbenzylphosphonate

: 213127-96-9
diethyl [(4-{(2S)-2-[(tert-butoxycarbonyl)amino]-3-hydroxypropyl}phenyl)methyl]phosphonate

Guidance literature:: Multi-step reaction with 8 steps

1: N-bromosuccinimide; AIBN / CCl₄ / 3 h / 90 °C

2: 76 percent / NaH / tetrahydrofuran / 0.5 h / 20 °C

3: 79 percent / NaBH₄ / methanol / 2 h / 20 °C

4: 97 percent / lipase PS / tetrahydrofuran / 2 h / 25 °C / Enzymatic reaction; 2 equiv. vinyl acetate

5: Jones reagent / acetone / 4 h / 20 °C

6: 52 percent / diphenylphosphoryl azide; triethylamine / benzene / 24 h / Heating

7: 88 percent / H₂ / Pd-C / ethyl acetate / 12 h / 20 °C / 760 Torr

8: 77 percent / aq. MeOH; K₂CO₃ / 1 h

With methanol; sodium tetrahydroborate; N-Bromosuccinimide; jones reagent; Lipase PS; 2,2'-azobis(isobutyronitrile); diphenylphosphoranyl azide; hydrogen; sodium hydride; potassium carbonate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; tetrachloromethane; ethyl acetate; acetone; benzene; 1: Bromination / 2: Substitution / 3: Reduction / 4: Acetylation / 5: Oxidation / 6: Rearrangement / 7: Substitution / 8: Hydrolysis;
DOI:10.1016/S0040-4020(98)00586-9