methyl 4-<(di-tert-butylphosphono)fluoromethyl>-N-(benzyloxycarbonyl)-D,L-phenylalaninate

Base Information

Chemical Name:methyl 4-<(di-tert-butylphosphono)fluoromethyl>-N-(benzyloxycarbonyl)-D,L-phenylalaninate
CAS No.:146745-50-8
Molecular Formula:C₂₇H₃₇FNO₇P
Molecular Weight:537.565
Hs Code.:

Synonyms:methyl 4-<(di-tert-butylphosphono)fluoromethyl>-N-(benzyloxycarbonyl)-D,L-phenylalaninate

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Chemical Property of methyl 4-<(di-tert-butylphosphono)fluoromethyl>-N-(benzyloxycarbonyl)-D,L-phenylalaninate

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Technology Process of methyl 4-<(di-tert-butylphosphono)fluoromethyl>-N-(benzyloxycarbonyl)-D,L-phenylalaninate

There total 7 articles about methyl 4-<(di-tert-butylphosphono)fluoromethyl>-N-(benzyloxycarbonyl)-D,L-phenylalaninate 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: 69.0%

: 146745-46-2
methyl 4-<(di-tert-butylphosphono)hydroxymethyl>-N-(benzyloxycarbonyl)-D,L-phenylalaninate

: 146745-50-8
methyl 4-<(di-tert-butylphosphono)fluoromethyl>-N-(benzyloxycarbonyl)-D,L-phenylalaninate

Guidance literature:: With diethylamino-sulfur trifluoride; In chloroform; 1) -78 deg C, 10 min, 2) rt, 20 min;
DOI:10.1021/jo00058a009

Reference yield:

: 81172-89-6
terephthalaldehyde mono(diethylacetal)

: 146745-50-8
methyl 4-<(di-tert-butylphosphono)fluoromethyl>-N-(benzyloxycarbonyl)-D,L-phenylalaninate

Guidance literature:: Multi-step reaction with 6 steps

1: 1) NaH / 1) THF, oil, -78 deg C, 40 min, 2) 0 deg C to rt, 2.5 h

2: 1 N HCl / CHCl₃ / Ambient temperature

3: 57 percent / NaOMe / 1) -78 deg C, 5 min, 2) 0 deg C, 1 h

4: 92 percent / H₂ / 10percent Pd/C / methanol / 3 h / 2068.6 Torr

5: 85 percent / Et₃N / tetrahydrofuran / 0.33 h / 0 °C

6: 69 percent / Et₂NSF₃ / CHCl₃ / 1) -78 deg C, 10 min, 2) rt, 20 min

With hydrogenchloride; diethylamino-sulfur trifluoride; hydrogen; sodium methylate; sodium hydride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; chloroform;
DOI:10.1021/jo00058a009

Reference yield:

: 13086-84-5
di-tert-butyl phosphite

: 146745-50-8
methyl 4-<(di-tert-butylphosphono)fluoromethyl>-N-(benzyloxycarbonyl)-D,L-phenylalaninate

Guidance literature:: Multi-step reaction with 6 steps

1: 1) NaH / 1) THF, oil, -78 deg C, 40 min, 2) 0 deg C to rt, 2.5 h

2: 1 N HCl / CHCl₃ / Ambient temperature

3: 57 percent / NaOMe / 1) -78 deg C, 5 min, 2) 0 deg C, 1 h

4: 92 percent / H₂ / 10percent Pd/C / methanol / 3 h / 2068.6 Torr

5: 85 percent / Et₃N / tetrahydrofuran / 0.33 h / 0 °C

6: 69 percent / Et₂NSF₃ / CHCl₃ / 1) -78 deg C, 10 min, 2) rt, 20 min

With hydrogenchloride; diethylamino-sulfur trifluoride; hydrogen; sodium methylate; sodium hydride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; chloroform;
DOI:10.1021/jo00058a009