Methanesulfonic acid (2S,3R)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-oxo-1-p-tolyl-azetidin-3-yl ester

Base Information

• Chemical Name: Methanesulfonic acid (2S,3R)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-oxo-1-p-tolyl-azetidin-3-yl ester
• CAS No.: 869283-88-5
• Molecular Formula: C₁₆H₂₁NO₆S
• Molecular Weight: 355.412
• Mol file: 869283-88-5.mol

Synonyms:Methanesulfonic acid (2S,3R)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-oxo-1-p-tolyl-azetidin-3-yl ester

Chemical Property of Methanesulfonic acid (2S,3R)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-oxo-1-p-tolyl-azetidin-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methanesulfonic acid (2S,3R)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-oxo-1-p-tolyl-azetidin-3-yl ester

There total 1 articles about Methanesulfonic acid (2S,3R)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-oxo-1-p-tolyl-azetidin-3-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:

(3R,4S)-3-Benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-p-tolyl-azetidin-2-one (143159-98-2) → Methanesulfonic acid (2S,3R)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-oxo-1-p-tolyl-azetidin-3-yl ester (869283-88-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / HCOONH₄ / Pd/C / methanol / 0.5 h / Heating

2: 91 percent / Et₃N / CH₂Cl₂ / 2 h / -10 - 20 °C

With ammonium formate; triethylamine; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1055/s-2005-872263

Reference yield: 96.0%

Methanesulfonic acid (2S,3R)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-oxo-1-p-tolyl-azetidin-3-yl ester (869283-88-5) → Methanesulfonic acid (2S,3R)-2-((S)-1,2-dihydroxy-ethyl)-4-oxo-1-p-tolyl-azetidin-3-yl ester (869283-91-0)

Guidance literature:

With toluene-4-sulfonic acid; In tetrahydrofuran; Heating;

DOI:10.1055/s-2005-872263

Reference yield:

Methanesulfonic acid (2S,3R)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-oxo-1-p-tolyl-azetidin-3-yl ester (869283-88-5) → (1S,5R)-6-p-Tolyl-3-oxa-6-aza-bicyclo[3.1.0]hexan-2-one

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / aq. PTSA / tetrahydrofuran / Heating

2: 90 percent / NaIO₄*silica gel / methanol / 3.5 h / 20 °C

3: 80 percent / NaBH₄ / methanol; tetrahydrofuran / 3 h / 20 °C

4: 83 percent / HCl / methanol / 17 h / Heating

With hydrogenchloride; sodium tetrahydroborate; sodium periodate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol;

DOI:10.1055/s-2005-872263

upstream raw materials:

(3R,4S)-3-Benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-p-tolyl-azetidin-2-one

Downstream raw materials:

Methanesulfonic acid (2S,3R)-2-((S)-1,2-dihydroxy-ethyl)-4-oxo-1-p-tolyl-azetidin-3-yl ester

Methanesulfonic acid (2R,3R)-2-formyl-4-oxo-1-p-tolyl-azetidin-3-yl ester

Methanesulfonic acid (2S,3R)-2-hydroxymethyl-4-oxo-1-p-tolyl-azetidin-3-yl ester