5-{3-[5-((3R,4R,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-oxo-piperidin-3-ylcarbamoyl)-pentylcarbamoyl]-4-nitro-phenyldisulfanyl}-2-nitro-benzoic acid 2,5-dioxo-pyrrolidin-1-yl ester

Base Information

• Chemical Name: 5-{3-[5-((3R,4R,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-oxo-piperidin-3-ylcarbamoyl)-pentylcarbamoyl]-4-nitro-phenyldisulfanyl}-2-nitro-benzoic acid 2,5-dioxo-pyrrolidin-1-yl ester
• CAS No.: 250737-32-7
• Molecular Formula: C₃₀H₃₂N₆O₁₄S₂
• Molecular Weight: 764.748

Synonyms:

Chemical Property of 5-{3-[5-((3R,4R,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-oxo-piperidin-3-ylcarbamoyl)-pentylcarbamoyl]-4-nitro-phenyldisulfanyl}-2-nitro-benzoic acid 2,5-dioxo-pyrrolidin-1-yl ester

Chemical Property:

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Technology Process of 5-{3-[5-((3R,4R,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-oxo-piperidin-3-ylcarbamoyl)-pentylcarbamoyl]-4-nitro-phenyldisulfanyl}-2-nitro-benzoic acid 2,5-dioxo-pyrrolidin-1-yl ester

There total 6 articles about 5-{3-[5-((3R,4R,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-oxo-piperidin-3-ylcarbamoyl)-pentylcarbamoyl]-4-nitro-phenyldisulfanyl}-2-nitro-benzoic acid 2,5-dioxo-pyrrolidin-1-yl 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: 41.0%

5,5'-dithiobis(2-nitrobenzoic acid succinimidyl diester) (60129-38-6) + 2-[(6-aminohexanoyl)amino]-2-deoxy-D-glucono-δ-lactam (1054644-86-8) → 5-{3-[5-((3R,4R,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-oxo-piperidin-3-ylcarbamoyl)-pentylcarbamoyl]-4-nitro-phenyldisulfanyl}-2-nitro-benzoic acid 2,5-dioxo-pyrrolidin-1-yl ester (250737-32-7)

Guidance literature:

In N,N-dimethyl-formamide; at 4 ℃; for 16h;

DOI:10.1002/(sici)1099-0690(199910)1999:10<2593::aid-ejoc2593>3.0.co;2-c

Reference yield:

6-(benzyloxycarbonylamino)hexanoic acid (1947-00-8) → 5-{3-[5-((3R,4R,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-oxo-piperidin-3-ylcarbamoyl)-pentylcarbamoyl]-4-nitro-phenyldisulfanyl}-2-nitro-benzoic acid 2,5-dioxo-pyrrolidin-1-yl ester (250737-32-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / PyBOP; DiPEA / CH₂Cl₂ / 0.5 h

2: 88 percent / hydrogen; formic acid / 10 percent Pd/C / propan-2-ol; ethyl acetate; H₂O / 2 h

3: 41 percent / dimethylformamide / 16 h / 4 °C

With formic acid; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol; 1: Acylation / 2: Reduction / 3: Acylation;

DOI:10.1002/(sici)1099-0690(199910)1999:10<2593::aid-ejoc2593>3.0.co;2-c

Reference yield:

2-amino-3,4,6-tri-O-benzyl-2-deoxy-D-glucono-δ-lactam (250737-20-3) → 5-{3-[5-((3R,4R,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-oxo-piperidin-3-ylcarbamoyl)-pentylcarbamoyl]-4-nitro-phenyldisulfanyl}-2-nitro-benzoic acid 2,5-dioxo-pyrrolidin-1-yl ester (250737-32-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / PyBOP; DiPEA / CH₂Cl₂ / 0.5 h

2: 88 percent / hydrogen; formic acid / 10 percent Pd/C / propan-2-ol; ethyl acetate; H₂O / 2 h

3: 41 percent / dimethylformamide / 16 h / 4 °C

With formic acid; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol; 1: Acylation / 2: Reduction / 3: Acylation;

DOI:10.1002/(sici)1099-0690(199910)1999:10<2593::aid-ejoc2593>3.0.co;2-c

upstream raw materials:

5,5'-dithiobis(2-nitrobenzoic acid succinimidyl diester)

2-[(6-aminohexanoyl)amino]-2-deoxy-D-glucono-δ-lactam

6-(benzyloxycarbonylamino)hexanoic acid

2-amino-3,4,6-tri-O-benzyl-2-deoxy-D-glucono-δ-lactam

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