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

Base Information

• Chemical Name: (3aR,5S,6R,6aR)-6-Benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde
• CAS No.: 149207-10-3
• Molecular Formula: C₁₆H₂₀O₅
• Molecular Weight: 292.332
• Mol file: 149207-10-3.mol

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

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

There total 12 articles about (3aR,5S,6R,6aR)-6-Benzyloxymethyl-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: 92.0%

3-C-(benzyloxymethyl)-3-deoxy-1,2-O-isopropylidene-α-D-allofuranose (85315-68-0) → (3aR,5S,6R,6aR)-6-Benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde (149207-10-3)

Guidance literature:

With palladium(II) acetate; In dichloromethane; at 22 ℃; for 0.5h;

DOI:10.1016/S0957-4166(00)86089-9

Reference yield:

3-C-(benzyloxymethyl)-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranose (85315-67-9) → (3aR,5S,6R,6aR)-6-Benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde (149207-10-3)

Guidance literature:

Multi-step reaction with 2 steps

1: acetic acid

2: NaIO₄

With sodium periodate; acetic acid;

DOI:10.1081/NCN-120022618

Reference yield:

((3aR,5S,6R,6aR)-tetrahydro-2,2-dimethyl-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)furo[2,3-d][1,3]dioxol-6-yl)methanol (69832-48-0) → (3aR,5S,6R,6aR)-6-Benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde (149207-10-3)

Guidance literature:

Multi-step reaction with 3 steps

1: acetic acid

2: NaIO₄

With sodium periodate; acetic acid;

DOI:10.1081/NCN-120022618

upstream raw materials:

3-C-(benzyloxymethyl)-3-deoxy-1,2-O-isopropylidene-α-D-allofuranose

((3aR,5S,6R,6aR)-tetrahydro-2,2-dimethyl-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)furo[2,3-d][1,3]dioxol-6-yl)methanol

O¹,O²;O⁵,O⁶-diisopropylidene-3-methylene-α-D-ribo-3-deoxy-hexofuranose

1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose

Downstream raw materials:

3-benzyloxymethyl-3-deoxy-1,2-isopropylidene-4-(17-tridec-1-enyl)-α-D-erythrofuranose

((3aR,6S,6aR)-6-Benzyloxymethyl-5-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-methanol

5-O-benzoyl-3-deoxy-3-<(benzyloxy)methyl>-1,2-O-isopropylidene-α-D-ribofuranose

(3R,4S,5R)-5-<(benzoyloxy)methyl>-4-<(benzyloxy)methyl>tetrahydrofuran-3-ol