(3aS,5R,6R,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde

Base Information

• Chemical Name: (3aS,5R,6R,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde
• CAS No.: 145772-63-0
• Molecular Formula: C₁₅H₁₈O₅
• Molecular Weight: 278.305
• Mol file: 145772-63-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 14 articles about (3aS,5R,6R,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde 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: 67.0%

[(3aS,5S,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methanol (391201-57-3) → (3aS,5R,6R,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde (145772-63-0)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃; for 4h;

DOI:10.1016/S0957-4166(02)00752-8

Reference yield:

1,2-O-isopropylidene-α-L-xylofuranose (114861-22-2) → (3aS,5R,6R,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde (145772-63-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 93 percent / PYRIDINE / 22 h / 50 °C

2: 94 percent / nAh; n-Bu₄NI / tetrahydrofuran / 4 h

3: 83 percent / HBr; AcOH / 0.02 h / 10 °C

4: 67 percent / Dess-Martin periodinane / CH₂Cl₂ / 4 h / 0 - 20 °C

With pyridine; hydrogen bromide; tetra-(n-butyl)ammonium iodide; sodium hydride; Dess-Martin periodane; acetic acid; In tetrahydrofuran; dichloromethane; 4: Dess-Martin oxidation;

DOI:10.1016/S0957-4166(02)00752-8

Reference yield:

(3aS,3bR,7aS,8aS)-2,2,5,5-tetramethyltetrahydro-3aH-[1,3]dioxolo[4',5':4,5]furo[3,2-d][1,3]dioxane (131156-47-3) → (3aS,5R,6R,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde (145772-63-0)

Guidance literature:

Multi-step reaction with 7 steps

1: acetic acid / water

2: pyridine; dichloromethane / 0.5 h / -78 °C

3: triethylamine / acetonitrile / 0 - 20 °C

4: tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butylammonium methanoate; triphenylphosphine / dichloromethane

5: sodium hydride / tetrahydrofuran / 0 °C / Inert atmosphere

6: sodium methylate / methanol

7: pyridine; dicyclohexyl-carbodiimide; trifluoroacetic acid / dimethyl sulfoxide / 16 h / 20 °C

With pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium methylate; n-butylammonium methanoate; sodium hydride; acetic acid; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; dimethyl sulfoxide; acetonitrile; 7: Moffat oxidation;

DOI:10.1135/cccc2011038

upstream raw materials:

[(3aS,5S,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methanol

β-L-arabinose

1,2-O-Isopropylidene-5-O-triphenylmethyl-α-L-xylofuranose

1,2-O-isopropylidene-α-L-xylofuranose

Downstream raw materials:

6,6,7,7-tetradehydro-6,7-dideoxy-α-D-gluco-heptofuranose

6,6,7,7-tetradehydro-6,7-dideoxy-β-L-ido-heptofuranose

diethyl (5S)-(3-O-benzyl-1,2-O-isopropylidene-α-L-xylofuranos-5-C-yl)phoshonate

diethyl (4S)-(1,3-di-O-acetyl-2-O-benzyl-α-L-threofuranos-4-yl)phosphonate