(R)-2-[(S)-2-(2-Acetoxy-propionylamino)-propionylamino]-4-[(1S,5R)-5-tert-butoxycarbonylamino-6-(N'-tert-butoxycarbonyl-hydrazino)-1-(carboxymethyl-carbamoyl)-6-oxo-hexylcarbamoyl]-butyric acid benzyl ester

Base Information

• Chemical Name: (R)-2-[(S)-2-(2-Acetoxy-propionylamino)-propionylamino]-4-[(1S,5R)-5-tert-butoxycarbonylamino-6-(N'-tert-butoxycarbonyl-hydrazino)-1-(carboxymethyl-carbamoyl)-6-oxo-hexylcarbamoyl]-butyric acid benzyl ester
• CAS No.: 76490-19-2
• Molecular Formula: C₃₉H₅₉N₇O₁₅
• Molecular Weight: 865.935

Synonyms:

Chemical Property of (R)-2-[(S)-2-(2-Acetoxy-propionylamino)-propionylamino]-4-[(1S,5R)-5-tert-butoxycarbonylamino-6-(N'-tert-butoxycarbonyl-hydrazino)-1-(carboxymethyl-carbamoyl)-6-oxo-hexylcarbamoyl]-butyric acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-[(S)-2-(2-Acetoxy-propionylamino)-propionylamino]-4-[(1S,5R)-5-tert-butoxycarbonylamino-6-(N'-tert-butoxycarbonyl-hydrazino)-1-(carboxymethyl-carbamoyl)-6-oxo-hexylcarbamoyl]-butyric acid benzyl ester

There total 24 articles about (R)-2-[(S)-2-(2-Acetoxy-propionylamino)-propionylamino]-4-[(1S,5R)-5-tert-butoxycarbonylamino-6-(N'-tert-butoxycarbonyl-hydrazino)-1-(carboxymethyl-carbamoyl)-6-oxo-hexylcarbamoyl]-butyric acid benzyl 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:

di-tert-butyl dicarbonate (24424-99-5) → (R)-2-[(S)-2-(2-Acetoxy-propionylamino)-propionylamino]-4-[(1S,5R)-5-tert-butoxycarbonylamino-6-(N'-tert-butoxycarbonyl-hydrazino)-1-(carboxymethyl-carbamoyl)-6-oxo-hexylcarbamoyl]-butyric acid benzyl ester (76490-19-2,76548-48-6,76548-52-2,76548-57-7,79390-11-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 93 percent / Et₃N / dioxane; H₂O

2: 1.) i-BuOCOCl, N-methylmorpholine / 1.) CH₂Cl₂, -10 to -15 deg C, 20 min, 2.) -10 -> 0 deg C, 1.5 h

3: 89 percent / hydrogen / 10percent Pd-C / methanol; acetic acid

4: 1.) i-BuOCOCl, N-methylmorpholine, 2.) BSA / 1.) CH₂Cl₂, -10 to -15 deg C, 30 min, 2.) CH₂Cl₂, DMF, 0 deg C, 2 h

With 4-methyl-morpholine; benzenesulfonamide; hydrogen; triethylamine; isobutyl chloroformate; palladium on activated charcoal; In 1,4-dioxane; methanol; water; acetic acid;

DOI:10.1021/ja00413a070

Reference yield:

(2S,6R)-2-Benzyloxycarbonylamino-6-tert-butoxycarbonylamino-7-(N'-tert-butoxycarbonyl-hydrazino)-7-oxo-heptanoic acid (76489-90-2) → (R)-2-[(S)-2-(2-Acetoxy-propionylamino)-propionylamino]-4-[(1S,5R)-5-tert-butoxycarbonylamino-6-(N'-tert-butoxycarbonyl-hydrazino)-1-(carboxymethyl-carbamoyl)-6-oxo-hexylcarbamoyl]-butyric acid benzyl ester (76490-19-2,76548-48-6,76548-52-2,76548-57-7,79390-11-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) i-BuOCOCl, N-methylmorpholine / 1.) CH₂Cl₂, -10 to -15 deg C, 20 min, 2.) -10 -> 0 deg C, 1.5 h

2: 89 percent / hydrogen / 10percent Pd-C / methanol; acetic acid

3: 1.) i-BuOCOCl, N-methylmorpholine, 2.) BSA / 1.) CH₂Cl₂, -10 to -15 deg C, 30 min, 2.) CH₂Cl₂, DMF, 0 deg C, 2 h

With 4-methyl-morpholine; benzenesulfonamide; hydrogen; isobutyl chloroformate; palladium on activated charcoal; In methanol; acetic acid;

DOI:10.1021/ja00413a070

Reference yield:

(2S,6R)-6-Amino-2-benzyloxycarbonylamino-7-(N'-tert-butoxycarbonyl-hydrazino)-7-oxo-heptanoic acid (27299-51-0) → (R)-2-[(S)-2-(2-Acetoxy-propionylamino)-propionylamino]-4-[(1S,5R)-5-tert-butoxycarbonylamino-6-(N'-tert-butoxycarbonyl-hydrazino)-1-(carboxymethyl-carbamoyl)-6-oxo-hexylcarbamoyl]-butyric acid benzyl ester (76490-19-2,76548-48-6,76548-52-2,76548-57-7,79390-11-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 93 percent / Et₃N / dioxane; H₂O

2: 1.) i-BuOCOCl, N-methylmorpholine / 1.) CH₂Cl₂, -10 to -15 deg C, 20 min, 2.) -10 -> 0 deg C, 1.5 h

3: 89 percent / hydrogen / 10percent Pd-C / methanol; acetic acid

4: 1.) i-BuOCOCl, N-methylmorpholine, 2.) BSA / 1.) CH₂Cl₂, -10 to -15 deg C, 30 min, 2.) CH₂Cl₂, DMF, 0 deg C, 2 h

With 4-methyl-morpholine; benzenesulfonamide; hydrogen; triethylamine; isobutyl chloroformate; palladium on activated charcoal; In 1,4-dioxane; methanol; water; acetic acid;

DOI:10.1021/ja00413a070

upstream raw materials:

D-lactoyl(OAc)-L-Ala-L-Glu(OH)OBzl

C₂₂H₄₃N₅O₈Si

(2R)-1-chloro-1-oxopropan-2-yl acetate

tert-Boc-L-Ala-L-Glu(OH)OBzl

Downstream raw materials:

(2R,6S)-2-Amino-6-{(R)-4-carboxy-4-[(S)-2-(2-hydroxy-propionylamino)-propionylamino]-butyrylamino}-6-(carboxymethyl-carbamoyl)-hexanoic acid

D-lactoyl-D-Ala-γ-D-Glu(α-OH)-(L)meso-A₂pm(L)-Gly

L-lactoyl-L-Ala-γ-D-Glu(α-OH)-(L)meso-A₂pm(L)-Gly

D-lactoyl-L-Ala-γ-L-Glu(α-OH)-(L)meso-A₂pm(L)-Gly

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