Benzoic acid (2R,3S,4R,5R)-4-azido-5-[1,3]dioxolan-2-yl-3-hydroxy-tetrahydro-furan-2-ylmethyl ester

Base Information

• Chemical Name: Benzoic acid (2R,3S,4R,5R)-4-azido-5-[1,3]dioxolan-2-yl-3-hydroxy-tetrahydro-furan-2-ylmethyl ester
• CAS No.: 781642-67-9
• Molecular Formula: C₁₅H₁₇N₃O₆
• Molecular Weight: 335.316
• Mol file: 781642-67-9.mol

Synonyms:Benzoic acid (2R,3S,4R,5R)-4-azido-5-[1,3]dioxolan-2-yl-3-hydroxy-tetrahydro-furan-2-ylmethyl ester

Chemical Property of Benzoic acid (2R,3S,4R,5R)-4-azido-5-[1,3]dioxolan-2-yl-3-hydroxy-tetrahydro-furan-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2R,3S,4R,5R)-4-azido-5-[1,3]dioxolan-2-yl-3-hydroxy-tetrahydro-furan-2-ylmethyl ester

There total 1 articles about Benzoic acid (2R,3S,4R,5R)-4-azido-5-[1,3]dioxolan-2-yl-3-hydroxy-tetrahydro-furan-2-ylmethyl ester 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: 59.0%

2,5-anhydro-3-azido-6-O-benzoyl-4-O-benzyl-3-deoxy-D-allose ethylene acetal (228399-09-5) → Benzoic acid (2R,3S,4R,5R)-4-azido-5-[1,3]dioxolan-2-yl-3-hydroxy-tetrahydro-furan-2-ylmethyl ester (781642-67-9)

Guidance literature:

With titanium tetrachloride; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/j.tetlet.2004.07.104

Reference yield: 84.0%

benzoyl chloride (98-88-4) + Benzoic acid (2R,3S,4R,5R)-4-azido-5-[1,3]dioxolan-2-yl-3-hydroxy-tetrahydro-furan-2-ylmethyl ester (781642-67-9) → 2,5-anhydro-3-azido-4,6-di-O-benzoyl-3-deoxy-D-allose ethylene acetal (781642-66-8)

Guidance literature:

With pyridine; at 20 ℃; for 72h;

DOI:10.1016/j.tetlet.2004.07.104

Reference yield:

Benzoic acid (2R,3S,4R,5R)-4-azido-5-[1,3]dioxolan-2-yl-3-hydroxy-tetrahydro-furan-2-ylmethyl ester (781642-67-9) → ethyl 2-(2-benzamido-5-O-benzoyl-2-deoxy-β-D-ribofuranosyl)thiazole-4-carboxylate (781642-74-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 84 percent / pyridine / 72 h / 20 °C

2: TFA; aq. HCl / 264 h / 4 °C

3: NH₂OH*HCl; NaOAc / ethanol; CH₂Cl₂ / 2 h / 20 °C

4: MsCl; pyridine / 2.5 h / -15 - 20 °C

5: 82 percent / H₂S; DMAP / ethanol / 8 h / 20 °C

6: 55 percent / ethanol / 1.33 h / Heating

With pyridine; hydrogenchloride; dmap; hydrogen sulfide; hydroxylamine hydrochloride; sodium acetate; methanesulfonyl chloride; trifluoroacetic acid; In ethanol; dichloromethane;

DOI:10.1016/j.tetlet.2004.07.104

upstream raw materials:

2,5-anhydro-3-azido-6-O-benzoyl-4-O-benzyl-3-deoxy-D-allose ethylene acetal

Downstream raw materials:

2,5-anhydro-3-azido-4,6-di-O-benzoyl-3-deoxy-D-allose ethylene acetal

2,5-anhydro-3-azido-4,6-di-O-benzoyl-3-deoxy-D-allononitrile

2,5-anhydro-3-benzamido-6-O-benzoyl-3-deoxy-D-allonothioamide

ethyl 2-(2-benzamido-5-O-benzoyl-2-deoxy-β-D-ribofuranosyl)thiazole-4-carboxylate