(3S,4R)-4-[(4-Benzyloxycarbonylamino-butyl)-tert-butoxycarbonyl-amino]-6-methyl-3-triisopropylsilanyloxy-heptanoic acid (1S,2S,3S)-1-isopropyl-2-methoxymethoxy-3-pentafluorophenyloxycarbonyl-butyl ester

Base Information

Chemical Name:(3S,4R)-4-[(4-Benzyloxycarbonylamino-butyl)-tert-butoxycarbonyl-amino]-6-methyl-3-triisopropylsilanyloxy-heptanoic acid (1S,2S,3S)-1-isopropyl-2-methoxymethoxy-3-pentafluorophenyloxycarbonyl-butyl ester
CAS No.:192211-89-5
Molecular Formula:C₅₀H₇₇F₅N₂O₁₁Si
Molecular Weight:1005.25
Hs Code.:

(3S,4R)-4-[(4-Benzyloxycarbonylamino-butyl)-tert-butoxycarbonyl-amino]-6-methyl-3-triisopropylsilanyloxy-heptanoic acid (1S,2S,3S)-1-isopropyl-2-methoxymethoxy-3-pentafluorophenyloxycarbonyl-butyl ester

Synonyms:(3S,4R)-4-[(4-Benzyloxycarbonylamino-butyl)-tert-butoxycarbonyl-amino]-6-methyl-3-triisopropylsilanyloxy-heptanoic acid (1S,2S,3S)-1-isopropyl-2-methoxymethoxy-3-pentafluorophenyloxycarbonyl-butyl ester

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Chemical Property of (3S,4R)-4-[(4-Benzyloxycarbonylamino-butyl)-tert-butoxycarbonyl-amino]-6-methyl-3-triisopropylsilanyloxy-heptanoic acid (1S,2S,3S)-1-isopropyl-2-methoxymethoxy-3-pentafluorophenyloxycarbonyl-butyl ester

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Technology Process of (3S,4R)-4-[(4-Benzyloxycarbonylamino-butyl)-tert-butoxycarbonyl-amino]-6-methyl-3-triisopropylsilanyloxy-heptanoic acid (1S,2S,3S)-1-isopropyl-2-methoxymethoxy-3-pentafluorophenyloxycarbonyl-butyl ester

There total 12 articles about (3S,4R)-4-[(4-Benzyloxycarbonylamino-butyl)-tert-butoxycarbonyl-amino]-6-methyl-3-triisopropylsilanyloxy-heptanoic acid (1S,2S,3S)-1-isopropyl-2-methoxymethoxy-3-pentafluorophenyloxycarbonyl-butyl 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: 68.0%

: 771-61-9
2,3,4,5,6-pentafluorophenol

: 192211-79-3
(3S,4R)-4-[(4-Benzyloxycarbonylamino-butyl)-tert-butoxycarbonyl-amino]-6-methyl-3-triisopropylsilanyloxy-heptanoic acid (1S,2S,3S)-3-carboxy-1-isopropyl-2-methoxymethoxy-butyl ester

: 192211-89-5
(3S,4R)-4-[(4-Benzyloxycarbonylamino-butyl)-tert-butoxycarbonyl-amino]-6-methyl-3-triisopropylsilanyloxy-heptanoic acid (1S,2S,3S)-1-isopropyl-2-methoxymethoxy-3-pentafluorophenyloxycarbonyl-butyl ester

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; for 12h; Ambient temperature;
DOI:10.1021/jo9623696

Reference yield:

: 23032-21-5
D-leucine methyl ester

: 192211-89-5
(3S,4R)-4-[(4-Benzyloxycarbonylamino-butyl)-tert-butoxycarbonyl-amino]-6-methyl-3-triisopropylsilanyloxy-heptanoic acid (1S,2S,3S)-1-isopropyl-2-methoxymethoxy-3-pentafluorophenyloxycarbonyl-butyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: 83 percent / AcOH, Na(OAc)3BH / 1,2-dichloro-ethane / 12 h

2: 87 percent / Et₃N / CH₂Cl₂ / Heating

3: 97 percent / H₂ / Pd/C / methanol; ethyl acetate / 3 h / 2068.6 Torr

4: 93 percent / Et₃N / CH₂Cl₂

5: 91 percent / LiOH*H₂O / tetrahydrofuran; H₂O / 4 h / 0 °C

6: 67 percent / DCC / CH₂Cl₂ / 12 h / Ambient temperature

7: 1) LDA / 1) THF, -78 deg C, 1 h, 2) THF, -78 deg C, 4 h

8: 78 percent / KBH₄ / ethanol / 0 deg C 1 h; ambient temperature, 24 h

9: 78 percent / 2,6-lutidine / CH₂Cl₂ / 6 h / 0 °C

10: 89 percent / aq. HOAc / tetrahydrofuran / 16 h

11: 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one / CH₂Cl₂ / 0.5 h

12: aq. KMnO₄, NaH₂PO₄ / 2-methyl-propan-2-ol; diethyl ether / 1 h / 25 °C

13: 68 percent / DCC, DMAP / CH₂Cl₂ / 12 h / Ambient temperature

With 2,6-dimethylpyridine; dmap; lithium hydroxide; potassium permanganate; sodium dihydrogenphosphate; potassium borohydride; hydrogen; sodium tris(acetoxy)borohydride; Dess-Martin periodane; acetic acid; triethylamine; dicyclohexyl-carbodiimide; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; tert-butyl alcohol;
DOI:10.1021/jo9623696

Reference yield:

: 192211-70-4
2-(4-azidobutylamino)-4-methylpentanoic acid methyl ester

: 192211-89-5
(3S,4R)-4-[(4-Benzyloxycarbonylamino-butyl)-tert-butoxycarbonyl-amino]-6-methyl-3-triisopropylsilanyloxy-heptanoic acid (1S,2S,3S)-1-isopropyl-2-methoxymethoxy-3-pentafluorophenyloxycarbonyl-butyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 87 percent / Et₃N / CH₂Cl₂ / Heating

2: 97 percent / H₂ / Pd/C / methanol; ethyl acetate / 3 h / 2068.6 Torr

3: 93 percent / Et₃N / CH₂Cl₂

4: 91 percent / LiOH*H₂O / tetrahydrofuran; H₂O / 4 h / 0 °C

5: 67 percent / DCC / CH₂Cl₂ / 12 h / Ambient temperature

6: 1) LDA / 1) THF, -78 deg C, 1 h, 2) THF, -78 deg C, 4 h

7: 78 percent / KBH₄ / ethanol / 0 deg C 1 h; ambient temperature, 24 h

8: 78 percent / 2,6-lutidine / CH₂Cl₂ / 6 h / 0 °C

9: 89 percent / aq. HOAc / tetrahydrofuran / 16 h

10: 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one / CH₂Cl₂ / 0.5 h

11: aq. KMnO₄, NaH₂PO₄ / 2-methyl-propan-2-ol; diethyl ether / 1 h / 25 °C

12: 68 percent / DCC, DMAP / CH₂Cl₂ / 12 h / Ambient temperature

With 2,6-dimethylpyridine; dmap; lithium hydroxide; potassium permanganate; sodium dihydrogenphosphate; potassium borohydride; hydrogen; Dess-Martin periodane; acetic acid; triethylamine; dicyclohexyl-carbodiimide; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; tert-butyl alcohol;
DOI:10.1021/jo9623696