(3S,4S,9S,10S)-4,10-dibenzoyloxy-2,8-dihydroxy-3,9-dimethoxycarbonyl-6,12-dioxo-1,7-diazatricyclo[7.3.0.0^3,7]dodecane

Base Information

• Chemical Name: (3S,4S,9S,10S)-4,10-dibenzoyloxy-2,8-dihydroxy-3,9-dimethoxycarbonyl-6,12-dioxo-1,7-diazatricyclo[7.3.0.0^3,7]dodecane
• CAS No.: 418763-37-8
• Molecular Formula: C₂₈H₂₆N₂O₁₂
• Molecular Weight: 582.521

Synonyms:(3S,4S,9S,10S)-4,10-dibenzoyloxy-2,8-dihydroxy-3,9-dimethoxycarbonyl-6,12-dioxo-1,7-diazatricyclo[7.3.0.0^3,7]dodecane

Chemical Property of (3S,4S,9S,10S)-4,10-dibenzoyloxy-2,8-dihydroxy-3,9-dimethoxycarbonyl-6,12-dioxo-1,7-diazatricyclo[7.3.0.0^3,7]dodecane

Chemical Property:

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Technology Process of (3S,4S,9S,10S)-4,10-dibenzoyloxy-2,8-dihydroxy-3,9-dimethoxycarbonyl-6,12-dioxo-1,7-diazatricyclo[7.3.0.0^3,7]dodecane

There total 4 articles about (3S,4S,9S,10S)-4,10-dibenzoyloxy-2,8-dihydroxy-3,9-dimethoxycarbonyl-6,12-dioxo-1,7-diazatricyclo[7.3.0.0^3,7]dodecane 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: 42.0%

(2R,3S)-6-benzoyloxy-2-hydroxymethyl-2-methoxycarbonylpyrrolidin-5-one (418763-23-2) → (3S,4S,9S,10S)-4,10-dibenzoyloxy-2,8-dihydroxy-3,9-dimethoxycarbonyl-6,12-dioxo-1,7-diazatricyclo[7.3.0.03,7]dodecane (418763-37-8)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 20 ℃; for 3.41667h;

DOI:10.1039/b108056n

Reference yield:

benzoyl chloride (98-88-4) → (3S,4S,9S,10S)-4,10-dibenzoyloxy-2,8-dihydroxy-3,9-dimethoxycarbonyl-6,12-dioxo-1,7-diazatricyclo[7.3.0.03,7]dodecane (418763-37-8)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / CH₂Cl₂ / 24 h / Heating

2: 97 percent / CF₃CH₂OH; HS(CH₂)3SH; HCl / 22 h / 20 °C

3: 42 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 3.42 h / -78 - 20 °C

With pyridine; 1.3-propanedithiol; hydrogenchloride; oxalyl dichloride; 2,2,2-trifluoroethanol; dimethyl sulfoxide; triethylamine; In dichloromethane; 3: Swern oxidation;

DOI:10.1039/b108056n

Reference yield:

(2R,5R,6S)-1-aza-2-(tert-butyl)-6-hydroxy-5-methoxycarbonyl-3-oxa-8-oxobicyclo[3.3.0]octane (418763-17-4) → (3S,4S,9S,10S)-4,10-dibenzoyloxy-2,8-dihydroxy-3,9-dimethoxycarbonyl-6,12-dioxo-1,7-diazatricyclo[7.3.0.03,7]dodecane (418763-37-8)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / CH₂Cl₂ / 24 h / Heating

2: 97 percent / CF₃CH₂OH; HS(CH₂)3SH; HCl / 22 h / 20 °C

3: 42 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 3.42 h / -78 - 20 °C

With pyridine; 1.3-propanedithiol; hydrogenchloride; oxalyl dichloride; 2,2,2-trifluoroethanol; dimethyl sulfoxide; triethylamine; In dichloromethane; 3: Swern oxidation;

DOI:10.1039/b108056n

upstream raw materials:

(2R,3S)-6-benzoyloxy-2-hydroxymethyl-2-methoxycarbonylpyrrolidin-5-one

benzoyl chloride

(2R,5R,6S)-1-aza-2-(tert-butyl)-6-hydroxy-5-methoxycarbonyl-3-oxa-8-oxobicyclo[3.3.0]octane

(2R,5R,6S)-6-benzoyloxy-2-(tert-butyl)-5-methoxycarbonyl-8-oxo-3-oxa-1-azabicyclo[3.3.0]octane

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