(3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-oxiranyl-tetrahydro-furo[2,3-d][1,3]dioxole

Base Information

• Chemical Name: (3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-oxiranyl-tetrahydro-furo[2,3-d][1,3]dioxole
• CAS No.: 868078-60-8
• Molecular Formula: C₁₆H₂₀O₅
• Molecular Weight: 292.332

Synonyms:(3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-oxiranyl-tetrahydro-furo[2,3-d][1,3]dioxole

Chemical Property of (3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-oxiranyl-tetrahydro-furo[2,3-d][1,3]dioxole

Chemical Property:

Purity/Quality:

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Technology Process of (3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-oxiranyl-tetrahydro-furo[2,3-d][1,3]dioxole

There total 3 articles about (3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-oxiranyl-tetrahydro-furo[2,3-d][1,3]dioxole 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: 62.0%

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol (22529-61-9) → (3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-oxiranyl-tetrahydro-furo[2,3-d][1,3]dioxole (868078-60-8)

Guidance literature:

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol; With pyridine; iodine; triphenylphosphine; In toluene; at 20 ℃;

With sodium hydride; In toluene; at 20 ℃; for 0.166667h;

DOI:10.1016/j.tetlet.2006.08.090

Reference yield:

Benzoic acid (S)-2-((3aR,5S,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-methanesulfonyloxy-ethyl ester (882689-03-4) → (3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-oxiranyl-tetrahydro-furo[2,3-d][1,3]dioxole (868078-60-8)

Guidance literature:

With potassium tert-butylate; In dichloromethane; tert-butyl alcohol; at 0 ℃; for 16h;

Reference yield:

→ (3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-oxiranyl-tetrahydro-furo[2,3-d][1,3]dioxole (868078-60-8)

Guidance literature:

aus d. entspr. Tosylat, NaOCH3;

DOI:10.1007/BF00912947

upstream raw materials:

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

Benzoic acid (S)-2-((3aR,5S,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-methanesulfonyloxy-ethyl ester

Downstream raw materials:

3-O-benzyl-1,2-O-isopropylidene-6-deoxy-6-(4-pentyn-1-ol)-α-glucofuranose

3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose

1,6-anhydro-3-O-benzyl-β-D-glucopyranose

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