(2R,3R,4R)-3-(benzyloxy)-4-[(benzyloxy)methyl]tetrahydro-4-hydroxyfuran-2-carbaldehyde

Base Information

• Chemical Name: (2R,3R,4R)-3-(benzyloxy)-4-[(benzyloxy)methyl]tetrahydro-4-hydroxyfuran-2-carbaldehyde
• CAS No.: 221229-55-6
• Molecular Formula: C₂₀H₂₂O₅
• Molecular Weight: 342.392

Synonyms:(2R,3R,4R)-3-(benzyloxy)-4-[(benzyloxy)methyl]tetrahydro-4-hydroxyfuran-2-carbaldehyde

Chemical Property of (2R,3R,4R)-3-(benzyloxy)-4-[(benzyloxy)methyl]tetrahydro-4-hydroxyfuran-2-carbaldehyde

Chemical Property:

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Technology Process of (2R,3R,4R)-3-(benzyloxy)-4-[(benzyloxy)methyl]tetrahydro-4-hydroxyfuran-2-carbaldehyde

There total 4 articles about (2R,3R,4R)-3-(benzyloxy)-4-[(benzyloxy)methyl]tetrahydro-4-hydroxyfuran-2-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: 75.0%

(1R,4R,6R,7R)-7-benzyloxy-4-benzyloxymethyl-6-methoxy-2,5-dioxabicyclo[2.2.1]heptane → (2R,3R,4R)-3-(benzyloxy)-4-[(benzyloxy)methyl]tetrahydro-4-hydroxyfuran-2-carbaldehyde (221229-55-6)

Guidance literature:

With toluene-4-sulfonic acid; In tetrahydrofuran; water; at 20 ℃; Inert atmosphere;

DOI:10.1021/jo300936g

Reference yield:

3-O-benzyl-4-[(benzyloxy)methyl]-1,2-O-(1-methylethylidene)-5-O-(methylsulfonyl)-β-L-lyxofuranose (219854-34-9) → (2R,3R,4R)-3-(benzyloxy)-4-[(benzyloxy)methyl]tetrahydro-4-hydroxyfuran-2-carbaldehyde (221229-55-6)

Guidance literature:

Multi-step reaction with 3 steps

1: toluene-4-sulfonic acid / water / 20 °C / Inert atmosphere

2: potassium carbonate / methanol / 0 - 20 °C / Inert atmosphere

3: toluene-4-sulfonic acid / tetrahydrofuran; water / 20 °C / Inert atmosphere

With potassium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; water;

DOI:10.1021/jo300936g

Reference yield:

((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol (153186-10-8) → (2R,3R,4R)-3-(benzyloxy)-4-[(benzyloxy)methyl]tetrahydro-4-hydroxyfuran-2-carbaldehyde (221229-55-6)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / 1 h / 20 °C / Inert atmosphere

2: toluene-4-sulfonic acid / water / 20 °C / Inert atmosphere

3: potassium carbonate / methanol / 0 - 20 °C / Inert atmosphere

4: toluene-4-sulfonic acid / tetrahydrofuran; water / 20 °C / Inert atmosphere

With pyridine; potassium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; water;

DOI:10.1021/jo300936g

upstream raw materials:

3,5-di-O-benzyl-4-mesyloxymethyl-1-O-methyl-β-D-ribofuranose

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

3-O-benzyl-4-[(benzyloxy)methyl]-1,2-O-(1-methylethylidene)-5-O-(methylsulfonyl)-β-L-lyxofuranose

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