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

Base Information

Chemical Name:(3S,4R)-4-[(4-Benzyloxycarbonylamino-butyl)-tert-butoxycarbonyl-amino]-6-methyl-3-triisopropylsilanyloxy-heptanoic acid (1S,2S,3R)-4-hydroxy-1-isopropyl-2-methoxymethoxy-3-methyl-butyl ester
CAS No.:192211-78-2
Molecular Formula:C₄₄H₈₀N₂O₁₀Si
Molecular Weight:825.212
Hs Code.:

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

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

There total 10 articles about (3S,4R)-4-[(4-Benzyloxycarbonylamino-butyl)-tert-butoxycarbonyl-amino]-6-methyl-3-triisopropylsilanyloxy-heptanoic acid (1S,2S,3R)-4-hydroxy-1-isopropyl-2-methoxymethoxy-3-methyl-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: 89.0%

: 192211-77-1
(3S,4R)-4-[(4-Benzyloxycarbonylamino-butyl)-tert-butoxycarbonyl-amino]-6-methyl-3-triisopropylsilanyloxy-heptanoic acid (1S,2S,3R)-4-(tert-butyl-dimethyl-silanyloxy)-1-isopropyl-2-methoxymethoxy-3-methyl-butyl ester

: 192211-78-2
(3S,4R)-4-[(4-Benzyloxycarbonylamino-butyl)-tert-butoxycarbonyl-amino]-6-methyl-3-triisopropylsilanyloxy-heptanoic acid (1S,2S,3R)-4-hydroxy-1-isopropyl-2-methoxymethoxy-3-methyl-butyl ester

Guidance literature:: With acetic acid; In tetrahydrofuran; for 16h;
DOI:10.1021/jo9623696

Reference yield:

: 23032-21-5
D-leucine methyl ester

: 192211-78-2
(3S,4R)-4-[(4-Benzyloxycarbonylamino-butyl)-tert-butoxycarbonyl-amino]-6-methyl-3-triisopropylsilanyloxy-heptanoic acid (1S,2S,3R)-4-hydroxy-1-isopropyl-2-methoxymethoxy-3-methyl-butyl ester

Guidance literature:: Multi-step reaction with 10 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

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

Reference yield:

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

: 192211-78-2
(3S,4R)-4-[(4-Benzyloxycarbonylamino-butyl)-tert-butoxycarbonyl-amino]-6-methyl-3-triisopropylsilanyloxy-heptanoic acid (1S,2S,3R)-4-hydroxy-1-isopropyl-2-methoxymethoxy-3-methyl-butyl ester

Guidance literature:: Multi-step reaction with 9 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

With 2,6-dimethylpyridine; lithium hydroxide; potassium borohydride; hydrogen; acetic acid; triethylamine; dicyclohexyl-carbodiimide; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; ethyl acetate;
DOI:10.1021/jo9623696