(5R)-3-benzyloxymethyl-5-[(4R)-2-oxo-1,3,2-dioxathiolan-4-yl]-2-isoxazoline

Base Information

• Chemical Name: (5R)-3-benzyloxymethyl-5-[(4R)-2-oxo-1,3,2-dioxathiolan-4-yl]-2-isoxazoline
• CAS No.: 877463-66-6
• Molecular Formula: C₁₃H₁₅NO₅S
• Molecular Weight: 297.332
• Mol file: 877463-66-6.mol

Synonyms:(5R)-3-benzyloxymethyl-5-[(4R)-2-oxo-1,3,2-dioxathiolan-4-yl]-2-isoxazoline

Chemical Property of (5R)-3-benzyloxymethyl-5-[(4R)-2-oxo-1,3,2-dioxathiolan-4-yl]-2-isoxazoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R)-3-benzyloxymethyl-5-[(4R)-2-oxo-1,3,2-dioxathiolan-4-yl]-2-isoxazoline

There total 3 articles about (5R)-3-benzyloxymethyl-5-[(4R)-2-oxo-1,3,2-dioxathiolan-4-yl]-2-isoxazoline 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: 85.0%

(5R)-5-[(1R)-1,2-dihydroxyethyl]-3-benzyloxymethyl-4,5-dihydrooxazole (334999-23-4) → (5R)-3-benzyloxymethyl-5-[(4R)-2-oxo-1,3,2-dioxathiolan-4-yl]-2-isoxazoline (877463-66-6)

Guidance literature:

With pyridine; thionyl chloride; In dichloromethane; at 0 - 20 ℃; for 2h;

DOI:10.1021/jo0517388

Reference yield:

(5R)-3-benzyloxymethyl-5-[(1R)-1,2-O-cyclohexylidene-1,2-dihydroxyethyl]-2-isoxazoline (877463-64-4) → (5R)-3-benzyloxymethyl-5-[(4R)-2-oxo-1,3,2-dioxathiolan-4-yl]-2-isoxazoline (877463-66-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / acetic acid / H₂O / 80 °C

2: 85 percent / pyridine; SOCl₂ / CH₂Cl₂ / 2 h / 0 - 20 °C

With pyridine; thionyl chloride; acetic acid; In dichloromethane; water;

DOI:10.1021/jo0517388

Reference yield:

((2-nitroethoxy)methyl)benzene (87976-52-1) → (5R)-3-benzyloxymethyl-5-[(4R)-2-oxo-1,3,2-dioxathiolan-4-yl]-2-isoxazoline (877463-66-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 18 percent / 1,4-phenylenediisocyanate; triethylamine / toluene / 42 h / Heating

2: 89 percent / acetic acid / H₂O / 80 °C

3: 85 percent / pyridine; SOCl₂ / CH₂Cl₂ / 2 h / 0 - 20 °C

With pyridine; thionyl chloride; acetic acid; 1,4-diisocyanatobenzene; triethylamine; In dichloromethane; water; toluene;

DOI:10.1021/jo0517388

upstream raw materials:

(5R)-5-[(1R)-1,2-dihydroxyethyl]-3-benzyloxymethyl-4,5-dihydrooxazole

(5R)-3-benzyloxymethyl-5-[(1R)-1,2-O-cyclohexylidene-1,2-dihydroxyethyl]-2-isoxazoline

((2-nitroethoxy)methyl)benzene

Downstream raw materials:

(5R)-3-benzyloxymethyl-5-[(4R)-2,2-dioxo-1,3,2-dioxathiolan-4-yl]-2-isoxazoline

(2R,4R,5R)-3-benzyloxymethyl-4,5-dihydroxypiperidine

(2R,4R,5R)-3-benzyloxymethyl-4-hydroxypiperidinium 5-sulfate

(2S,3R)-1,3-dihydroxy-1,3-O-isopropylidene-4-[(2R,4R,5R)-2-benzyloxymethyl-4,5-dihydroxypiperidinium-1-yl]butane-2-sulfate