3-Deoxy-D-xylo-hexofuranose tetraacetate

Base Information

• Chemical Name: 3-Deoxy-D-xylo-hexofuranose tetraacetate
• CAS No.: 23655-60-9
• Molecular Formula: C₁₄H₂₀O₉
• Molecular Weight: 332.307
• Mol file: 23655-60-9.mol

Synonyms:3-Deoxy-D-xylo-hexofuranose tetraacetate

Chemical Property of 3-Deoxy-D-xylo-hexofuranose tetraacetate

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-Deoxy-D-xylo-hexofuranose tetraacetate

There total 13 articles about 3-Deoxy-D-xylo-hexofuranose tetraacetate 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%

(S)-1-((3aR,5S,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethane-1,2-diyl diacetate + acetic anhydride (108-24-7) + acetic acid (64-19-7,77671-22-8) → (2S,3R,5S)-5-((S)-1,2-diacetoxyethyl)tetrahydrofuran-2,3-diyl diacetate (23655-60-9)

Guidance literature:

With sulfuric acid; In dichloromethane; at 0 - 22 ℃; for 4h;

Reference yield:

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → (2S,3R,5S)-5-((S)-1,2-diacetoxyethyl)tetrahydrofuran-2,3-diyl diacetate (23655-60-9)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 1H-imidazole; sodium hydride / mineral oil; tetrahydrofuran / 0.25 h / 0 - 10 °C

1.2: 1 h / 20 °C

1.3: 2 h / 0 - 20 °C

2.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 6 h / 120 °C / Inert atmosphere

3.1: acetic acid / water / 16 h / 20 °C

4.1: pyridine / Petroleum ether / 12 h / 0 - 20 °C

5.1: potassium hexamethylsilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

6.1: sodium hydride / mineral oil; 1,2-dimethoxyethane / 4 h / 0 - 60 °C / Inert atmosphere

7.1: diethylazodicarboxylate; triphenylphosphine / tetrahydrofuran / 10 h / 0 - 18 °C / Inert atmosphere

8.1: methanol; potassium carbonate / 0.5 h / 20 °C

9.1: hydrogen; palladium 10% on activated carbon / methanol / 16 h / 20 °C / 3620.13 Torr

10.1: triethylamine; dmap / dichloromethane / 16 h / 0 - 25 °C

11.1: sulfuric acid / dichloromethane / 4 h / 0 - 22 °C

With pyridine; 1H-imidazole; methanol; dmap; 2,2'-azobis(isobutyronitrile); sulfuric acid; palladium 10% on activated carbon; hydrogen; tri-n-butyl-tin hydride; potassium hexamethylsilazane; sodium hydride; potassium carbonate; acetic acid; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; water; toluene; mineral oil; Petroleum ether;

Reference yield:

(S)-2-(benzyloxy)-1-((3aR,5S,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethyl 4-nitrobenzoate → (2S,3R,5S)-5-((S)-1,2-diacetoxyethyl)tetrahydrofuran-2,3-diyl diacetate (23655-60-9)

Guidance literature:

Multi-step reaction with 4 steps

1: methanol; potassium carbonate / 0.5 h / 20 °C

2: hydrogen; palladium 10% on activated carbon / methanol / 16 h / 20 °C / 3620.13 Torr

3: triethylamine; dmap / dichloromethane / 16 h / 0 - 25 °C

4: sulfuric acid / dichloromethane / 4 h / 0 - 22 °C

With methanol; dmap; sulfuric acid; palladium 10% on activated carbon; hydrogen; potassium carbonate; triethylamine; In methanol; dichloromethane;

upstream raw materials:

acetic anhydride

3-deoxy-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

1,2,5,6-di-O-isopropylidene-α-D-glucofuranose-3-O-(S-methylxanthate)