(2R,4S,5S)-2-Benzyl-5-tert-butoxycarbonylamino-4-hydroxy-6-methyl-heptanoic acid

Base Information

• Chemical Name: (2R,4S,5S)-2-Benzyl-5-tert-butoxycarbonylamino-4-hydroxy-6-methyl-heptanoic acid
• CAS No.: 869494-47-3
• Molecular Formula: C₂₀H₃₁NO₅
• Molecular Weight: 365.47
• Mol file: 869494-47-3.mol

Synonyms:(2R,4S,5S)-2-Benzyl-5-tert-butoxycarbonylamino-4-hydroxy-6-methyl-heptanoic acid

Chemical Property of (2R,4S,5S)-2-Benzyl-5-tert-butoxycarbonylamino-4-hydroxy-6-methyl-heptanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4S,5S)-2-Benzyl-5-tert-butoxycarbonylamino-4-hydroxy-6-methyl-heptanoic acid

There total 11 articles about (2R,4S,5S)-2-Benzyl-5-tert-butoxycarbonylamino-4-hydroxy-6-methyl-heptanoic acid 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:

tert-butyl (S)-1-((2S,4R)-4-benzyltetrahydro-5-oxofuran-2-yl)-2-methylpropylcarbamate (214286-42-7) → (2R,4S,5S)-2-Benzyl-5-tert-butoxycarbonylamino-4-hydroxy-6-methyl-heptanoic acid (869494-47-3)

Guidance literature:

With lithium hydroxide; In 1,2-dimethoxyethane; at 23 ℃; for 0.5h;

DOI:10.1021/jm980537b

Reference yield:

tert-butyl (3S,4RS)-6-(ethoxycarbonyl)-4-hydroxy-2-methylhex-5-yn-3-ylcarbamate → (2R,4S,5S)-2-Benzyl-5-tert-butoxycarbonylamino-4-hydroxy-6-methyl-heptanoic acid (869494-47-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: H₂ / Pd(OH)2/C / ethyl acetate / 12 h

2.1: 772 mg / AcOH / toluene / 12 h / Heating

3.1: LDA / hexane; tetrahydrofuran / 0.5 h / -78 °C

3.2: 55 percent / hexane; tetrahydrofuran / 1.67 h / -78 °C

4.1: aq. LiOH / tetrahydrofuran / 0.67 h / 20 °C

With lithium hydroxide; hydrogen; acetic acid; lithium diisopropyl amide; palladium dihydroxide; In tetrahydrofuran; hexane; ethyl acetate; toluene;

DOI:10.1021/jm050548m

Reference yield:

trans-6-methylhept-4-enoic acid (61229-07-0) → (2R,4S,5S)-2-Benzyl-5-tert-butoxycarbonylamino-4-hydroxy-6-methyl-heptanoic acid (869494-47-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 41 percent / SOCl₂ / CHCl₃ / 0.75 h / Heating

2: 56 percent / Et₃N / tetrahydrofuran / 0.25 h / 0 °C

3: 1.) LDA, LiCl / 1.) THF, hexane, a) -78 deg C, 1.75 h, b) 0 deg C, 20 min, c) 23 deg C, 5 min, 2.) THF, 0 deg C, 30 min

4: N-bromosuccinimide, glacial AcOH / tetrahydrofuran; H₂O / a) 0 deg C, 15 min, b) reflux, 45 min

5: NaN₃ / dimethylformamide / 67 h / 50 °C

6: H₂ / 10 percent Pd/C / methanol / 16 h / 23 °C

7: aq. LiOH / 1,2-dimethoxy-ethane / 0.5 h / 23 °C

With lithium hydroxide; N-Bromosuccinimide; thionyl chloride; sodium azide; hydrogen; acetic acid; triethylamine; lithium chloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; chloroform; water; N,N-dimethyl-formamide;

DOI:10.1021/jm980537b

upstream raw materials:

tert-butyl (S)-1-((2S,4R)-4-benzyltetrahydro-5-oxofuran-2-yl)-2-methylpropylcarbamate

tert-butyl ((S)-2-methyl-1-((R)-5-oxotetrahydrofuran-2-yl)propyl)carbamate

(4S,5S)-5-tert-Butoxycarbonylamino-4-hydroxy-6-methyl-heptanoic acid ethyl ester

trans-6-methylhept-4-enoic acid

Downstream raw materials:

(2R,5S)-2-Benzyl-5-tert-butoxycarbonylamino-6-methyl-4-oxo-heptanoic acid

(2R,4S,5S)-2-benzyl-5-{[(tert-butoxy)carbonyl]amino}-4-[(tertbutyldimethylsilyl)oxy]-6-methylheptanoic acid

(E)-(S)-4-((2R,5S)-2-Benzyl-5-cyclopentylsulfanylcarbonylamino-6-methyl-4-oxo-heptanoylamino)-6-(trityl-carbamoyl)-hex-2-enoic acid ethyl ester

(E)-(S)-4-((2R,5S)-2-Benzyl-5-benzylsulfanylcarbonylamino-6-methyl-4-oxo-heptanoylamino)-6-(trityl-carbamoyl)-hex-2-enoic acid ethyl ester