(1'R,2'R,4S)-1'-Methylsulfonyloxy-1'-(2-phenyl-4,5-dihydrooxazol-4-yl)but-3'-en-2'-ol

Base Information

• Chemical Name: (1'R,2'R,4S)-1'-Methylsulfonyloxy-1'-(2-phenyl-4,5-dihydrooxazol-4-yl)but-3'-en-2'-ol
• CAS No.: 173531-23-2
• Molecular Formula: C₁₄H₁₇NO₅S
• Molecular Weight: 311.359

Synonyms:(1'R,2'R,4S)-1'-Methylsulfonyloxy-1'-(2-phenyl-4,5-dihydrooxazol-4-yl)but-3'-en-2'-ol

Chemical Property of (1'R,2'R,4S)-1'-Methylsulfonyloxy-1'-(2-phenyl-4,5-dihydrooxazol-4-yl)but-3'-en-2'-ol

Chemical Property:

Purity/Quality:

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Technology Process of (1'R,2'R,4S)-1'-Methylsulfonyloxy-1'-(2-phenyl-4,5-dihydrooxazol-4-yl)but-3'-en-2'-ol

There total 2 articles about (1'R,2'R,4S)-1'-Methylsulfonyloxy-1'-(2-phenyl-4,5-dihydrooxazol-4-yl)but-3'-en-2'-ol 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: 66.0%

Methanesulfonic acid (1R,2S,3R)-2,4-dihydroxy-3-methanesulfonyloxy-1-((S)-2-phenyl-4,5-dihydro-oxazol-4-yl)-butyl ester (173531-22-1) → (1'R,2'R,4S)-1'-Methylsulfonyloxy-1'-(2-phenyl-4,5-dihydrooxazol-4-yl)but-3'-en-2'-ol (173531-23-2)

Guidance literature:

With pyridine; iodine; triphenylphosphine; In toluene; at 60 - 70 ℃; for 1h;

DOI:10.1039/p19960000823

Reference yield:

Methanesulfonic acid (R)-((2R,4S,5R)-5-methanesulfonyloxy-2-methyl-[1,3]dioxan-4-yl)-((S)-2-phenyl-4,5-dihydro-oxazol-4-yl)-methyl ester (173531-21-0) → (1'R,2'R,4S)-1'-Methylsulfonyloxy-1'-(2-phenyl-4,5-dihydrooxazol-4-yl)but-3'-en-2'-ol (173531-23-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / thiophenol, TiCl₄ / CH₂Cl₂ / 2 h / 0 °C

2: 66 percent / I₂, Ph₃P, pyridine / toluene / 1 h / 60 - 70 °C

With pyridine; iodine; titanium tetrachloride; thiophenol; triphenylphosphine; In dichloromethane; toluene;

DOI:10.1039/p19960000823

Reference yield: 93.0%

(1'R,2'R,4S)-1'-Methylsulfonyloxy-1'-(2-phenyl-4,5-dihydrooxazol-4-yl)but-3'-en-2'-ol (173531-23-2) → (4S,1'S,2'R)-4-(1',2'-Epoxybut-3'-enyl)-2-phenyl-4,5-dihydrooxazole (173531-24-3)

Guidance literature:

With potassium carbonate; In methanol; 1.) 0 deg C, 30 min, 2.) r.t., 5 h;

DOI:10.1039/p19960000823

upstream raw materials:

Methanesulfonic acid (1R,2S,3R)-2,4-dihydroxy-3-methanesulfonyloxy-1-((S)-2-phenyl-4,5-dihydro-oxazol-4-yl)-butyl ester

Methanesulfonic acid (R)-((2R,4S,5R)-5-methanesulfonyloxy-2-methyl-[1,3]dioxan-4-yl)-((S)-2-phenyl-4,5-dihydro-oxazol-4-yl)-methyl ester

Downstream raw materials:

(4S,1'S,2'R)-4-(1',2'-Epoxybut-3'-enyl)-2-phenyl-4,5-dihydrooxazole

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

N-Benzoyl-D-erythro-C₁₈-sphingosine

erythro-4-(1-hydroxy-2-hexadecenyl)-2-phenyl-Δ²-oxazoline

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