allyl N-(benzyloxycarbonyl)-O-<4,O³-isopropylidene-4-<(tert-butyloxycarbonyl)amino>-3-hydroxy-5-methylhexanoyl>oxy-3-oxo-2,5-dimethylhexanoyl>-L-leucyl>-L-prolyl-(N,O-dimethyl-L-tyrosyl)>-L-threoninate

Base Information

• Chemical Name: allyl N-(benzyloxycarbonyl)-O-<4,O³-isopropylidene-4-<(tert-butyloxycarbonyl)amino>-3-hydroxy-5-methylhexanoyl>oxy-3-oxo-2,5-dimethylhexanoyl>-L-leucyl>-L-prolyl-(N,O-dimethyl-L-tyrosyl)>-L-threoninate
• CAS No.: 117710-16-4
• Molecular Formula: C₆₀H₈₇N₅O₁₆
• Molecular Weight: 1134.37

Synonyms:

Chemical Property of allyl N-(benzyloxycarbonyl)-O-<4,O³-isopropylidene-4-<(tert-butyloxycarbonyl)amino>-3-hydroxy-5-methylhexanoyl>oxy-3-oxo-2,5-dimethylhexanoyl>-L-leucyl>-L-prolyl-(N,O-dimethyl-L-tyrosyl)>-L-threoninate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl N-(benzyloxycarbonyl)-O-<4,O³-isopropylidene-4-<(tert-butyloxycarbonyl)amino>-3-hydroxy-5-methylhexanoyl>oxy-3-oxo-2,5-dimethylhexanoyl>-L-leucyl>-L-prolyl-(N,O-dimethyl-L-tyrosyl)>-L-threoninate

There total 10 articles about allyl N-(benzyloxycarbonyl)-O-<4,O³-isopropylidene-4-<(tert-butyloxycarbonyl)amino>-3-hydroxy-5-methylhexanoyl>oxy-3-oxo-2,5-dimethylhexanoyl>-L-leucyl>-L-prolyl-(N,O-dimethyl-L-tyrosyl)>-L-threoninate 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:

Boc-D-Val-OH (22838-58-0) → allyl N-(benzyloxycarbonyl)-O-<4,O3-isopropylidene-4-<(tert-butyloxycarbonyl)amino>-3-hydroxy-5-methylhexanoyl>oxy-3-oxo-2,5-dimethylhexanoyl>-L-leucyl>-L-prolyl-(N,O-dimethyl-L-tyrosyl)>-L-threoninate (117710-16-4,117773-52-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 98 percent / triethylamine (TEA) / tetrahydrofuran / 2 h / 0 - 5 °C

2: lithium diisopropylamide / 1.) THF, hexane, from -78 deg C to -70 deg C, 15 min

3: NaBH₄ / CH₂Cl₂; acetic acid / 1 h / 0 - 5 °C

4: p-toluenesulfonic acid / 1.) reflux, 3 h, 2.) room temperature, overnight

5: 98 percent / 2 M NaOH / methanol / 0 - 5 °C

6: 92 percent / triethylamine (TEA), 4-(dimethylamino)pyridine (DMAP), isopropenyl chlorocarbonate (IPCC) / CH₂Cl₂ / 0.25 h / -5 °C

7: 100 percent / H₂ / 10percent Pd/C / propan-2-ol / 760 Torr

8: 97 percent / triethylamine (TEA) / tetrahydrofuran / 2 h / 0 - 5 °C

9: lithium diisopropylamide / 1.) THF, hexane, from -78 deg C to -70 deg C, 15 min

10: triethylamine (TEA), CuI / CH₂Cl₂ / 0.5 h / Ambient temperature

With dmap; sodium hydroxide; sodium tetrahydroborate; copper(l) iodide; Isopropenyl chloroformate; hydrogen; toluene-4-sulfonic acid; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; acetic acid; isopropyl alcohol;

DOI:10.1021/jo00264a022

Reference yield:

(R)-4-tert-Butoxycarbonylamino-3-hydroxy-5-methyl-hexanoic acid ethyl ester (117710-06-2) → allyl N-(benzyloxycarbonyl)-O-<4,O3-isopropylidene-4-<(tert-butyloxycarbonyl)amino>-3-hydroxy-5-methylhexanoyl>oxy-3-oxo-2,5-dimethylhexanoyl>-L-leucyl>-L-prolyl-(N,O-dimethyl-L-tyrosyl)>-L-threoninate (117710-16-4,117773-52-1)

Guidance literature:

Multi-step reaction with 7 steps

1: p-toluenesulfonic acid / 1.) reflux, 3 h, 2.) room temperature, overnight

2: 98 percent / 2 M NaOH / methanol / 0 - 5 °C

3: 92 percent / triethylamine (TEA), 4-(dimethylamino)pyridine (DMAP), isopropenyl chlorocarbonate (IPCC) / CH₂Cl₂ / 0.25 h / -5 °C

4: 100 percent / H₂ / 10percent Pd/C / propan-2-ol / 760 Torr

5: 97 percent / triethylamine (TEA) / tetrahydrofuran / 2 h / 0 - 5 °C

6: lithium diisopropylamide / 1.) THF, hexane, from -78 deg C to -70 deg C, 15 min

7: triethylamine (TEA), CuI / CH₂Cl₂ / 0.5 h / Ambient temperature

With dmap; sodium hydroxide; copper(l) iodide; Isopropenyl chloroformate; hydrogen; toluene-4-sulfonic acid; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; isopropyl alcohol;

DOI:10.1021/jo00264a022

Reference yield:

ethyl (4R)-4-<(tert-butyloxycarbonyl)amino>-3-oxo-5-methylhexanoate (117710-05-1) → allyl N-(benzyloxycarbonyl)-O-<4,O3-isopropylidene-4-<(tert-butyloxycarbonyl)amino>-3-hydroxy-5-methylhexanoyl>oxy-3-oxo-2,5-dimethylhexanoyl>-L-leucyl>-L-prolyl-(N,O-dimethyl-L-tyrosyl)>-L-threoninate (117710-16-4,117773-52-1)

Guidance literature:

Multi-step reaction with 8 steps

1: NaBH₄ / CH₂Cl₂; acetic acid / 1 h / 0 - 5 °C

2: p-toluenesulfonic acid / 1.) reflux, 3 h, 2.) room temperature, overnight

3: 98 percent / 2 M NaOH / methanol / 0 - 5 °C

4: 92 percent / triethylamine (TEA), 4-(dimethylamino)pyridine (DMAP), isopropenyl chlorocarbonate (IPCC) / CH₂Cl₂ / 0.25 h / -5 °C

5: 100 percent / H₂ / 10percent Pd/C / propan-2-ol / 760 Torr

6: 97 percent / triethylamine (TEA) / tetrahydrofuran / 2 h / 0 - 5 °C

7: lithium diisopropylamide / 1.) THF, hexane, from -78 deg C to -70 deg C, 15 min

8: triethylamine (TEA), CuI / CH₂Cl₂ / 0.5 h / Ambient temperature

With dmap; sodium hydroxide; sodium tetrahydroborate; copper(l) iodide; Isopropenyl chloroformate; hydrogen; toluene-4-sulfonic acid; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; acetic acid; isopropyl alcohol;

DOI:10.1021/jo00264a022

upstream raw materials:

tert-butyl (4S)-4-<<(3S,4R)-N⁴,O³-isopropylidene-4-<(tert-butyloxycarbonyl)amino>-3-hydroxy-5-methylhexanoyl>oxy>-3-oxo-2,5-dimethylthiohexanoate

(S)-3-[(S)-2-{[(S)-1-((S)-2-Amino-4-methyl-pentanoyl)-pyrrolidine-2-carbonyl]-methyl-amino}-3-(4-methoxy-phenyl)-propionyloxy]-2-benzyloxycarbonylamino-butyric acid allyl ester

Boc-D-Val-OH

(R)-4-tert-Butoxycarbonylamino-3-hydroxy-5-methyl-hexanoic acid ethyl ester

Downstream raw materials:

N-(benzyloxycarbonyl)-O-<oxy-3-oxo-2,5-dimethylhexanoyl>-L-leucyl>-L-prolyl-(N,O-dimethyl-L-tyrosyl)>-L-threonine

glycyltyrosine

C₄₉H₇₁N₅O₁₄*C₂HF₃O₂

(5S,10S,14S,15R,18S,22S,24aS)-18-Amino-14-hydroxy-5-isobutyl-10,15-diisopropyl-22-(4-methoxy-benzyl)-8,19,23-trimethyl-tetradecahydro-11,20-dioxa-3a,6,16,23-tetraaza-cyclopentacyclotricosene-4,7,9,12,17,21,24-heptaone

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