(2S,3S,4R)-4-hydroxy-2,3-(oxazin-2-one)-1-(toluene-4-sulfonyl)pyrrolidine

Base Information

• Chemical Name: (2S,3S,4R)-4-hydroxy-2,3-(oxazin-2-one)-1-(toluene-4-sulfonyl)pyrrolidine
• CAS No.: 863392-53-4
• Molecular Formula: C₁₃H₁₆N₂O₅S
• Molecular Weight: 312.346
• Mol file: 863392-53-4.mol

Synonyms:(2S,3S,4R)-4-hydroxy-2,3-(oxazin-2-one)-1-(toluene-4-sulfonyl)pyrrolidine

Chemical Property of (2S,3S,4R)-4-hydroxy-2,3-(oxazin-2-one)-1-(toluene-4-sulfonyl)pyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4R)-4-hydroxy-2,3-(oxazin-2-one)-1-(toluene-4-sulfonyl)pyrrolidine

There total 5 articles about (2S,3S,4R)-4-hydroxy-2,3-(oxazin-2-one)-1-(toluene-4-sulfonyl)pyrrolidine 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: 28.0%

(S)-2-carbamoyloxymethyl-1-(toluene-4-sulfonyl)-2,5-dihydro-1H-pyrrole (863392-52-3) → (2S,3S,4R)-4-hydroxy-2,3-(oxazin-2-one)-1-(toluene-4-sulfonyl)pyrrolidine (863392-53-4) + (2S,3S,4R)-2-hydroxymethyl-3,4-(oxazol-2-one)-1-(toluene-4-sulfonyl)pyrrolidine (863392-54-5)

Guidance literature:

With sodium hydroxide; tert-butylhypochlorite; i-Pr₂NEt₂; potassium osmate; In propan-1-ol; water; for 2h;

DOI:10.1039/b711994a

Reference yield:

(2S,4S)-2-(carbamoyloxymethyl)-4-phenylselanyl-1-(toluene-4-sulfonyl)pyrrolidine (863392-59-0) → (2S,3S,4R)-4-hydroxy-2,3-(oxazin-2-one)-1-(toluene-4-sulfonyl)pyrrolidine (863392-53-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 52 percent / H₂O₂; pyridine / CH₂Cl₂ / 2 h / 0 °C

2: NaOH; tBuOCl; iPr₂NEt / K₂Os(OH)4O₂ / propan-1-ol; H₂O / 20 °C

With pyridine; sodium hydroxide; tert-butylhypochlorite; dihydrogen peroxide; N-ethyl-N,N-diisopropylamine; potassium osmate; In propan-1-ol; dichloromethane; water;

DOI:10.1016/j.tetlet.2005.06.025

Reference yield:

(2S,4R)-2-ethoxycarbonyl-1-(toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)pyrrolidine (118329-81-0) → (2S,3S,4R)-4-hydroxy-2,3-(oxazin-2-one)-1-(toluene-4-sulfonyl)pyrrolidine (863392-53-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 91 percent / NaBH₄; LiCl / tetrahydrofuran; ethanol / 3.5 h / 0 °C

2.1: CH₂Cl₂ / 2 h / 0 °C

2.2: 91 percent / K₂CO₃ / methanol / 4 h / 0 °C

3.1: 94 percent / NaBH₄ / tetrahydrofuran; ethanol / 2 h / Heating

4.1: 52 percent / H₂O₂; pyridine / CH₂Cl₂ / 2 h / 0 °C

5.1: NaOH; tBuOCl; iPr₂NEt / K₂Os(OH)4O₂ / propan-1-ol; H₂O / 20 °C

With pyridine; sodium hydroxide; sodium tetrahydroborate; tert-butylhypochlorite; dihydrogen peroxide; N-ethyl-N,N-diisopropylamine; lithium chloride; potassium osmate; In tetrahydrofuran; propan-1-ol; ethanol; dichloromethane; water;

DOI:10.1016/j.tetlet.2005.06.025

upstream raw materials:

(S)-2-carbamoyloxymethyl-1-(toluene-4-sulfonyl)-2,5-dihydro-1H-pyrrole

(2S,4S)-2-(carbamoyloxymethyl)-4-phenylselanyl-1-(toluene-4-sulfonyl)pyrrolidine

(2S,4R)-2-ethoxycarbonyl-1-(toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)pyrrolidine

(2S,4R)-2-(carbamoyloxymethyl)-1-(toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)pyrrolidine

Downstream raw materials:

(2S,3S,4R)-2-hydroxymethyl-3,4-(oxazol-2-one)-1-(toluene-4-sulfonyl)pyrrolidine