(2R,4R)-2-benzyloxycarbonylamino-4-carboxy-4-(3-indolylmethyl)-γ-butyrolactone

Base Information

• Chemical Name: (2R,4R)-2-benzyloxycarbonylamino-4-carboxy-4-(3-indolylmethyl)-γ-butyrolactone
• CAS No.: 535967-30-7
• Molecular Formula: C₂₂H₂₀N₂O₆
• Molecular Weight: 408.411
• Mol file: 535967-30-7.mol

Synonyms:(2R,4R)-2-benzyloxycarbonylamino-4-carboxy-4-(3-indolylmethyl)-γ-butyrolactone

Chemical Property of (2R,4R)-2-benzyloxycarbonylamino-4-carboxy-4-(3-indolylmethyl)-γ-butyrolactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4R)-2-benzyloxycarbonylamino-4-carboxy-4-(3-indolylmethyl)-γ-butyrolactone

There total 5 articles about (2R,4R)-2-benzyloxycarbonylamino-4-carboxy-4-(3-indolylmethyl)-γ-butyrolactone 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:

(2RS,4RS)-2-benzyloxycarbonylamino-4-carboxy-4-(3-indolylmethyl)-γ-butyrolactone → methyl 2-((1H-indol-3-yl)methyl)-4-(benzyloxycarbonylamino)-5-oxotetrahydrofuran-2-carboxylate (535967-29-4) + (2R,4R)-2-benzyloxycarbonylamino-4-carboxy-4-(3-indolylmethyl)-γ-butyrolactone (535967-30-7)

Guidance literature:

With CHIRALPAK AS; In ethanol; hexane; acetic acid; at 40 ℃; Overall yield = 70.7 %;

DOI:10.1248/cpb.c16-00286

Reference yield:

4-hydroxy-4-(3-indolylmethyl)-2-ketoglutaric acid (551958-84-0) → (2R,4R)-2-benzyloxycarbonylamino-4-carboxy-4-(3-indolylmethyl)-γ-butyrolactone (535967-30-7)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium hydroxide; hydroxylamine hydrochloride / water / 17.5 h / 5 °C / pH 7

2: rhodium contaminated with carbon; hydrogen; ammonium hydroxide / 24 h / 20 °C / 7500.75 Torr

3: sodium hydroxide / water / 20 °C

4: toluene-4-sulfonic acid / ethyl acetate / 3 h / 75 °C

5: CHIRALPAK AS / ethanol; hexane; acetic acid / 40 °C

With ammonium hydroxide; rhodium contaminated with carbon; hydroxylamine hydrochloride; hydrogen; toluene-4-sulfonic acid; sodium hydroxide; In ethanol; hexane; water; acetic acid; ethyl acetate;

DOI:10.1248/cpb.c16-00286

Reference yield:

Indole-3-pyruvic acid (392-12-1) → (2R,4R)-2-benzyloxycarbonylamino-4-carboxy-4-(3-indolylmethyl)-γ-butyrolactone (535967-30-7)

Guidance literature:

Multi-step reaction with 6 steps

1: sodium hydroxide / water / 16 h / 35 °C / pH 11 / Inert atmosphere

2: sodium hydroxide; hydroxylamine hydrochloride / water / 17.5 h / 5 °C / pH 7

3: rhodium contaminated with carbon; hydrogen; ammonium hydroxide / 24 h / 20 °C / 7500.75 Torr

4: sodium hydroxide / water / 20 °C

5: toluene-4-sulfonic acid / ethyl acetate / 3 h / 75 °C

6: CHIRALPAK AS / ethanol; hexane; acetic acid / 40 °C

With ammonium hydroxide; rhodium contaminated with carbon; hydroxylamine hydrochloride; hydrogen; toluene-4-sulfonic acid; sodium hydroxide; In ethanol; hexane; water; acetic acid; ethyl acetate;

DOI:10.1248/cpb.c16-00286

upstream raw materials:

Indole-3-pyruvic acid

4-hydroxy-4-(3-indolylmethyl)-2-ketoglutaric acid

Downstream raw materials:

(2R,4R)-2-benzyloxycarbonylamino-4-methylcarbamoyl-4-(3-indolylmethyl)-γ-butyrolactone