3-Azido-3-deoxy-4-hydroxy-methyl-1,2-O-isopropylidene-α-D-ribofuranose

Base Information

• Chemical Name: 3-Azido-3-deoxy-4-hydroxy-methyl-1,2-O-isopropylidene-α-D-ribofuranose
• CAS No.: 247025-10-1
• Molecular Formula: C9H15N3O5
• Molecular Weight: 245.235
• Hs Code.: 2940000080
• Mol file: 247025-10-1.mol

Synonyms:3-Azido-3-deoxy-4-hydroxy-methyl-1,2-O-isopropylidene-α-D-ribofuranose;3-Azido-3-deoxy-4-C-(hydroxyMethyl)-1,2-O-(1-Methylethylidene)-α-D-erythro-pentofuranose

Chemical Property of 3-Azido-3-deoxy-4-hydroxy-methyl-1,2-O-isopropylidene-α-D-ribofuranose

Chemical Property:

• Melting Point: 110-112°C
• PSA: 117.90000
• LogP: -0.65074
• Storage Temp.: -20°C Freezer
• Solubility.: DMF, DMSO, Ethanol, Methanol

Purity/Quality:

99% ^*data from raw suppliers

3-Azido-3-deoxy-4-hydroxy-methyl-1,2-O-isopropylidene-α-D-ribofuranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-Azido-3-deoxy-4-hydroxy-methyl-1,2-O-isopropylidene-α-D-ribofuranose

There total 10 articles about 3-Azido-3-deoxy-4-hydroxy-methyl-1,2-O-isopropylidene-α-D-ribofuranose 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: 94.0%

3-Azido-5-O-benzoyl-4-C-benzoyloxymethyl-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose (153914-98-8) → 3-Azido-3-deoxy-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose (247025-10-1)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 1h;

DOI:10.1039/b009109j

Reference yield: 86.0%

→ 3-Azido-5-O-benzoyl-4-C-benzoyloxymethyl-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose (153914-98-8) + 3-Azido-3-deoxy-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose (247025-10-1)

Guidance literature:

Reference yield:

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (350255-13-9) → 3-Azido-3-deoxy-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose (247025-10-1)

Guidance literature:

Multi-step reaction with 9 steps

1: sodium hydride / N,N-dimethyl-formamide / 2 h / 0 - 25 °C / Inert atmosphere

2: acetic acid / water / 20 °C

3: sodium periodate / water; 1,4-dioxane / 0 - 20 °C

4: sodium hydroxide; water / tetrahydrofuran / 0 - 20 °C

5: pyridine / 0 - 20 °C / Inert atmosphere

6: hydrogen; palladium 10% on activated carbon; acetic acid / methanol / 72 h / 50 °C

7: pyridine / dichloromethane / 2 h / -20 °C / Inert atmosphere

8: tetra-(n-butyl)ammonium iodide; sodium azide / N,N-dimethyl-formamide / 100 °C / Inert atmosphere

9: water; potassium carbonate / methanol / 5 h / 0 °C

With pyridine; sodium periodate; sodium azide; palladium 10% on activated carbon; water; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; acetic acid; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide;

upstream raw materials:

3-Azido-5-O-benzoyl-4-C-benzoyloxymethyl-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose

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

1-2,5-6 di-O-isopropylidene 3-O-benzyl α(D)gluco-pentoaldofuranose

1-2 O-isopropylidene 3-O-benzyl α(D)gluco-pentoaldofuranose

Downstream raw materials:

3'-azido-5'-O-tert-butyldiphenylsilyl-3'-deoxy-2'-O,4'-C-methylene-5-methyluridine

Acetic acid (3R,4S,5R)-4-azido-5-[(6-benzoylamino-purin-9-yl)-methoxy-methyl]-3-trimethylsilanyloxy-tetrahydro-furan-3-ylmethyl ester

3-azido-5-O-acetyl-3-deoxy-4-C-(p-toluenesulfonyloxymethyl)-1,2-O-isopropylidene-α-D-erythro-ribofuranose

3'-azido-5'-O-tert-butyldiphenylsilyl-3'-deoxy-4'-hydroxymethyl-1',2'-O-isopropylidene-α-D-ribofuranose