(-)-anti-2-(benzyloxymethyl)-2,3-dihydroxycyclopentyl acetate

Base Information

• Chemical Name: (-)-anti-2-(benzyloxymethyl)-2,3-dihydroxycyclopentyl acetate
• CAS No.: 952650-28-1
• Molecular Formula: C₁₅H₂₀O₅
• Molecular Weight: 280.321
• Mol file: 952650-28-1.mol

Synonyms:(-)-anti-2-(benzyloxymethyl)-2,3-dihydroxycyclopentyl acetate

Chemical Property of (-)-anti-2-(benzyloxymethyl)-2,3-dihydroxycyclopentyl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-anti-2-(benzyloxymethyl)-2,3-dihydroxycyclopentyl acetate

There total 3 articles about (-)-anti-2-(benzyloxymethyl)-2,3-dihydroxycyclopentyl acetate 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: 84.0%

(+)-2-(benzyloxymethyl)cyclopent-2-enyl acetate (952650-27-0) → (-)-anti-2-(benzyloxymethyl)-2,3-dihydroxycyclopentyl acetate (952650-28-1) + (-)-syn-2-(benzyloxymethyl)-2,3-dihydroxycyclopentyl acetate

Guidance literature:

With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In tetrahydrofuran; water; at 20 ℃; for 12h;

DOI:10.1016/j.tet.2007.07.053

Reference yield:

2-benzyloxymethyl-cyclopent-2-enone (911218-16-1) → (-)-anti-2-(benzyloxymethyl)-2,3-dihydroxycyclopentyl acetate (952650-28-1)

Guidance literature:

Multi-step reaction with 3 steps

1: (S)-nBu-CBS; BH₃*Me₂S / toluene; tetrahydrofuran / -10 °C

2: 98 percent / pyridine; N,N-dimethylaminopyridine / 1 h / 20 °C

3: 84 percent / N-methylmorpholine-N-oxide; OsO₄ / H₂O; tetrahydrofuran / 12 h / 20 °C

With pyridine; dmap; osmium(VIII) oxide; dimethylsulfide borane complex; 4-methylmorpholine N-oxide; In tetrahydrofuran; water; toluene;

DOI:10.1016/j.tet.2007.07.053

Reference yield:

(+)-2-(benzyloxymethyl)cyclopent-2-enol (952650-26-9) → (-)-anti-2-(benzyloxymethyl)-2,3-dihydroxycyclopentyl acetate (952650-28-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / pyridine; N,N-dimethylaminopyridine / 1 h / 20 °C

2: 84 percent / N-methylmorpholine-N-oxide; OsO₄ / H₂O; tetrahydrofuran / 12 h / 20 °C

With pyridine; dmap; osmium(VIII) oxide; 4-methylmorpholine N-oxide; In tetrahydrofuran; water;

DOI:10.1016/j.tet.2007.07.053

upstream raw materials:

(+)-2-(benzyloxymethyl)cyclopent-2-enyl acetate

2-benzyloxymethyl-cyclopent-2-enone

(+)-2-(benzyloxymethyl)cyclopent-2-enol

Downstream raw materials:

(-)-3a-(benzyloxymethyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl acetate