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

Base Information

• Chemical Name: N₁,N₆-di[2-methyl-1S-(methylcarbamoyl)propyl]-2R,5R-dibenzyloxy-3S,4S-dihydroxy hexanediamide
• CAS No.: 214139-60-3
• Molecular Formula: C₃₂H₄₆N₄O₈
• Molecular Weight: 614.739

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

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

Chemical Property:

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

There total 6 articles about N₁,N₆-di[2-methyl-1S-(methylcarbamoyl)propyl]-2R,5R-dibenzyloxy-3S,4S-dihydroxy hexanediamide 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: 69.0%

N1,N6-di[2-methyl-1S-(methylcarbamoyl)propyl]-2R,5R-dibenzyloxy-3S,4S-dihydroxy-3,4-O-iso-propylidenehexanediamide (214139-59-0) → N1,N6-di[2-methyl-1S-(methylcarbamoyl)propyl]-2R,5R-dibenzyloxy-3S,4S-dihydroxy hexanediamide (214139-60-3)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In water; acetonitrile; at 75 ℃; for 144h;

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

Reference yield:

L-valine N-methylamide (87105-26-8) → N1,N6-di[2-methyl-1S-(methylcarbamoyl)propyl]-2R,5R-dibenzyloxy-3S,4S-dihydroxy hexanediamide (214139-60-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / CH₂Cl₂; tetrahydrofuran / 18 h / 20 °C

2: 69 percent / DDQ / acetonitrile; H₂O / 144 h / 75 °C

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; acetonitrile; 1: Condensation / 2: Elimination;

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 hexanediamide (214139-60-3)

Guidance literature:

Multi-step reaction with 4 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

4: 69 percent / DDQ / acetonitrile; H₂O / 144 h / 75 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; tetrabutylammomium bromide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; pyridine; dichloromethane; water; acetonitrile; 1: Oxidation / 2: Condensation / 3: Condensation / 4: Elimination;

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

upstream raw materials:

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

L-valine N-methylamide

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

2,5-di-O-benzyl-3,4-O-isopropylidene-L-idaric acid

Downstream raw materials:

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

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