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

Base Information

Chemical Name:methyl 4-<(di-tert-butylphosphono)difluoromethyl>-N-(benzyloxycarbonyl)-D,L-phenylalaninate
CAS No.:146745-48-4
Molecular Formula:C₂₇H₃₆F₂NO₇P
Molecular Weight:555.556
Hs Code.:

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

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

Chemical Property:

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

There total 8 articles about methyl 4-<(di-tert-butylphosphono)difluoromethyl>-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: 54.0%

: 146745-47-3
methyl 4-<(di-tert-butylphosphono)oxomethyl>-N-(benzyloxycarbonyl)-D,L-phenylalaninate

: 146745-48-4
methyl 4-<(di-tert-butylphosphono)difluoromethyl>-N-(benzyloxycarbonyl)-D,L-phenylalaninate

Guidance literature:: With diethylamino-sulfur trifluoride; Ambient temperature;
DOI:10.1021/jo00058a009

Reference yield:

: 81172-89-6
terephthalaldehyde mono(diethylacetal)

: 146745-48-4
methyl 4-<(di-tert-butylphosphono)difluoromethyl>-N-(benzyloxycarbonyl)-D,L-phenylalaninate

Guidance literature:: Multi-step reaction with 7 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: 62 percent / celite, 4 A molecular sieves, pyridinium dichromate / CHCl₃ / 4 h / Ambient temperature

7: 54 percent / Et₂NSF₃ / Ambient temperature

With hydrogenchloride; dipyridinium dichromate; diethylamino-sulfur trifluoride; 4 A molecular sieve; Celite; hydrogen; sodium methylate; sodium hydride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; chloroform;
DOI:10.1021/jo00058a009

Reference yield:

: 132541-46-9
bis(1,1-dimethylethyl) <(4-formylphenyl)hydroxymethyl>phosphonate

: 146745-48-4
methyl 4-<(di-tert-butylphosphono)difluoromethyl>-N-(benzyloxycarbonyl)-D,L-phenylalaninate

Guidance literature:: Multi-step reaction with 5 steps

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

2: 92 percent / H₂ / 10percent Pd/C / methanol / 3 h / 2068.6 Torr

3: 85 percent / Et₃N / tetrahydrofuran / 0.33 h / 0 °C

4: 62 percent / celite, 4 A molecular sieves, pyridinium dichromate / CHCl₃ / 4 h / Ambient temperature

5: 54 percent / Et₂NSF₃ / Ambient temperature

With dipyridinium dichromate; diethylamino-sulfur trifluoride; 4 A molecular sieve; Celite; hydrogen; sodium methylate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; chloroform;
DOI:10.1021/jo00058a009