pivaloyloxymethyl 1,1-dioxide-6-β-[(benzyloxycarbonyl)methylsulfonamido]penicillinate

Base Information

• Chemical Name: pivaloyloxymethyl 1,1-dioxide-6-β-[(benzyloxycarbonyl)methylsulfonamido]penicillinate
• CAS No.: 1415712-69-4
• Molecular Formula: C₂₃H₃₀N₂O₁₁S₂
• Molecular Weight: 574.63
• Mol file: 1415712-69-4.mol

Synonyms:pivaloyloxymethyl 1,1-dioxide-6-β-[(benzyloxycarbonyl)methylsulfonamido]penicillinate

Chemical Property of pivaloyloxymethyl 1,1-dioxide-6-β-[(benzyloxycarbonyl)methylsulfonamido]penicillinate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of pivaloyloxymethyl 1,1-dioxide-6-β-[(benzyloxycarbonyl)methylsulfonamido]penicillinate

There total 5 articles about pivaloyloxymethyl 1,1-dioxide-6-β-[(benzyloxycarbonyl)methylsulfonamido]penicillinate 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: 96.0%

pivaloyloxymethyl 6-β-[(benzyloxycarbonyl)methylsulfonamido]penicillinate (1415712-67-2) → pivaloyloxymethyl 1,1-dioxide-6-β-[(benzyloxycarbonyl)methylsulfonamido]penicillinate (1415712-69-4)

Guidance literature:

With potassium permanganate; In water; acetic acid; at -15 - -10 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.tet.2011.10.100

Reference yield:

benzyloxycarbonylmethylsulfonyl chloride (159215-13-1) → pivaloyloxymethyl 1,1-dioxide-6-β-[(benzyloxycarbonyl)methylsulfonamido]penicillinate (1415712-69-4)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / dichloromethane / 1.25 h / 0 - 20 °C / Inert atmosphere

2: potassium permanganate / water; acetic acid / 1 h / -15 - -10 °C / Inert atmosphere

With potassium permanganate; triethylamine; In dichloromethane; water; acetic acid;

DOI:10.1016/j.tet.2011.10.100

Reference yield:

(2S,5R,6R)-2-[(2,2-dimethylpropanoyl)oxy]-methylpenicillanat-6-aminium 4-methylbenzenesulfonate (25031-03-2) → pivaloyloxymethyl 1,1-dioxide-6-β-[(benzyloxycarbonyl)methylsulfonamido]penicillinate (1415712-69-4)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / dichloromethane / 1.25 h / 0 - 20 °C / Inert atmosphere

2: potassium permanganate / water; acetic acid / 1 h / -15 - -10 °C / Inert atmosphere

With potassium permanganate; triethylamine; In dichloromethane; water; acetic acid;

DOI:10.1016/j.tet.2011.10.100

upstream raw materials:

benzyloxycarbonylmethylsulfonyl chloride

(2S,5R,6R)-2-[(2,2-dimethylpropanoyl)oxy]-methylpenicillanat-6-aminium 4-methylbenzenesulfonate

benzyl alcohol

pivaloyloxymethyl 6-β-[(benzyloxycarbonyl)methylsulfonamido]penicillinate