tert-butyl (4R)-2,2-dioxo-4-phenyl-1,2,3-oxathiazolidine-3-carboxylate

Base Information

• Chemical Name: tert-butyl (4R)-2,2-dioxo-4-phenyl-1,2,3-oxathiazolidine-3-carboxylate
• CAS No.: 1209467-60-6
• Molecular Formula: C13H17NO5S
• Molecular Weight: 299.348
• Hs Code.: 2934100090
• Mol file: 1209467-60-6.mol

Synonyms:tert-butyl (4R)-2,2-dioxo-4-phenyl-1,2,3-oxathiazolidine-3-carboxylate

Chemical Property of tert-butyl (4R)-2,2-dioxo-4-phenyl-1,2,3-oxathiazolidine-3-carboxylate

Chemical Property:

• Melting Point: 141 - 142 °C
• PSA: 81.29000
• LogP: 3.25850
• Sensitive.: air sensitive, store cold

Purity/Quality:

97% ^*data from raw suppliers

(4R)-4-Phenyl-1,2,3-oxathiazolidine-2,2-dioxide-3-carboxylic acid t-butyl ester, min. 97% ^*data from reagent suppliers

Safty Information:

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Technology Process of tert-butyl (4R)-2,2-dioxo-4-phenyl-1,2,3-oxathiazolidine-3-carboxylate

There total 3 articles about tert-butyl (4R)-2,2-dioxo-4-phenyl-1,2,3-oxathiazolidine-3-carboxylate 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: 94.0%

(R)-4-phenyl-[1,2,3]-oxathiazolidine 2,2-dioxide (1025505-76-3) + di-tert-butyl dicarbonate (24424-99-5) → (4R)-1,2,3-oxathiazolidine-3-carboxylic acid, 4-phenyl 1,1-dimethylethyl ester-2,2-dioxide (1209467-60-6)

Guidance literature:

With dmap; In dichloromethane; for 1h; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ol1017905

Reference yield:

(R)-N-(tert-butoxycarbonyl)phenylglycinol (67341-01-9,117049-14-6,138457-46-2,102089-74-7) → (4R)-1,2,3-oxathiazolidine-3-carboxylic acid, 4-phenyl 1,1-dimethylethyl ester-2,2-dioxide (1209467-60-6)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine; 1H-imidazole; thionyl chloride / dichloromethane / 4 h / -40 - 20 °C

2: sodium periodate; rhodium(III) chloride hydrate / acetonitrile; water / 0.5 h / 0 °C

With 1H-imidazole; sodium periodate; thionyl chloride; rhodium(III) chloride hydrate; triethylamine; In dichloromethane; water; acetonitrile;

DOI:10.1021/acscombsci.6b00050

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (4R)-1,2,3-oxathiazolidine-3-carboxylic acid, 4-phenyl 1,1-dimethylethyl ester-2,2-dioxide (1209467-60-6)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / dichloromethane / 24 h / 20 °C / Inert atmosphere

2: triethylamine; 1H-imidazole; thionyl chloride / dichloromethane / 4 h / -40 - 20 °C

3: sodium periodate; rhodium(III) chloride hydrate / acetonitrile; water / 0.5 h / 0 °C

With 1H-imidazole; sodium periodate; thionyl chloride; rhodium(III) chloride hydrate; triethylamine; In dichloromethane; water; acetonitrile;

DOI:10.1021/acscombsci.6b00050

upstream raw materials:

(R)-4-phenyl-[1,2,3]-oxathiazolidine 2,2-dioxide

di-tert-butyl dicarbonate

(R)-N-(tert-butoxycarbonyl)phenylglycinol

Downstream raw materials:

C₁₉H₂₂BrNO₃

(R)-tert-butyl 3-phenyl-3,4-dihydro-2H-1,4-benzoxazine-4-carboxylate

C₂₀H₂₄BrNO₃

(R)-tert-butyl 6-methyl-3-phenyl-2H-benzo[b][1,4]oxazine-4(3H)-carboxylate

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