N₁,N₆-di[2-methyl-1S-(methylcarbamoyl)propyl]-2R,5R-dibenzyloxy-3S,4S-dihydroxy-3,4-O-iso-propylidenehexanediamide

Base Information

• Chemical Name: N₁,N₆-di[2-methyl-1S-(methylcarbamoyl)propyl]-2R,5R-dibenzyloxy-3S,4S-dihydroxy-3,4-O-iso-propylidenehexanediamide
• CAS No.: 214139-59-0
• Molecular Formula: C₃₅H₅₀N₄O₈
• Molecular Weight: 654.804

Synonyms:N₁,N₆-di[2-methyl-1S-(methylcarbamoyl)propyl]-2R,5R-dibenzyloxy-3S,4S-dihydroxy-3,4-O-iso-propylidenehexanediamide

Chemical Property of N₁,N₆-di[2-methyl-1S-(methylcarbamoyl)propyl]-2R,5R-dibenzyloxy-3S,4S-dihydroxy-3,4-O-iso-propylidenehexanediamide

Chemical Property:

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Technology Process of N₁,N₆-di[2-methyl-1S-(methylcarbamoyl)propyl]-2R,5R-dibenzyloxy-3S,4S-dihydroxy-3,4-O-iso-propylidenehexanediamide

There total 7 articles about N₁,N₆-di[2-methyl-1S-(methylcarbamoyl)propyl]-2R,5R-dibenzyloxy-3S,4S-dihydroxy-3,4-O-iso-propylidenehexanediamide 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: 79.0%

L-valine N-methylamide (87105-26-8) + N1,N6-di-succinimidyl-2R,5R-dibenzyloxy-3S,4S-dihydroxy-3,4-O-isopropylidenehexanediester (288261-49-4) → N1,N6-di[2-methyl-1S-(methylcarbamoyl)propyl]-2R,5R-dibenzyloxy-3S,4S-dihydroxy-3,4-O-iso-propylidenehexanediamide (214139-59-0)

Guidance literature:

In tetrahydrofuran; dichloromethane; at 20 ℃; for 18h;

DOI:10.1016/S0040-4020(00)00220-9

Reference yield:

3,4-O-methylethylidene-D-mannitol (94925-98-1) → N1,N6-di[2-methyl-1S-(methylcarbamoyl)propyl]-2R,5R-dibenzyloxy-3S,4S-dihydroxy-3,4-O-iso-propylidenehexanediamide (214139-59-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 19.1 mmol / pyridine / 1 h / 20 °C

2: 15.5 mmol / NaH / dimethylformamide / -3 - 20 °C

3: dichloroacetic acid / CH₂Cl₂ / 2 h / 20 °C

4: TEMPO; NaOCl; Bu₄NBr / CH₂Cl₂; H₂O / 0.5 h / 0 °C

5: acetonitrile; pyridine / 15 h / 20 °C

6: 79 percent / CH₂Cl₂; tetrahydrofuran / 18 h / 20 °C

With dichloro-acetic acid; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; tetrabutylammomium bromide; sodium hydride; In tetrahydrofuran; pyridine; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 1: Methylation / 2: Alkylation / 3: detritylation / 4: Oxidation / 5: Condensation / 6: Condensation;

DOI:10.1016/S0040-4020(00)00220-9

Reference yield:

2,5-di-O-benzyl-3,4-O-isopropylidene-L-iditol (214139-57-8) → N1,N6-di[2-methyl-1S-(methylcarbamoyl)propyl]-2R,5R-dibenzyloxy-3S,4S-dihydroxy-3,4-O-iso-propylidenehexanediamide (214139-59-0)

Guidance literature:

Multi-step reaction with 3 steps

1: TEMPO; NaOCl; Bu₄NBr / CH₂Cl₂; H₂O / 0.5 h / 0 °C

2: acetonitrile; pyridine / 15 h / 20 °C

3: 79 percent / CH₂Cl₂; tetrahydrofuran / 18 h / 20 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; tetrabutylammomium bromide; In tetrahydrofuran; pyridine; dichloromethane; water; acetonitrile; 1: Oxidation / 2: Condensation / 3: Condensation;

DOI:10.1016/S0040-4020(00)00220-9

upstream raw materials:

L-valine N-methylamide

N₁,N₆-di-succinimidyl-2R,5R-dibenzyloxy-3S,4S-dihydroxy-3,4-O-isopropylidenehexanediester

2,5-di-O-benzyl-3,4-O-isopropylidene-L-iditol

3,4-O-methylethylidene-D-mannitol

Downstream raw materials:

N₁,N₆-di[2-methyl-1S-(methylcarbamoyl)propyl]-2R,5R-dibenzyloxy-3S,4S-dihydroxy hexanediamide

N₁,N₆-di[2-methyl-1S-(methylcarbamoyl)propyl]-2R,5R-dibenzyloxy-3S,4S-dihydroxy-3,4-O-iso-thiocarbonylhexanediamide

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