(3aR,5R,6S,6aR)-5-(azidomethyl)tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxol-6-yl 4-methylbenzenesulfonate

Base Information

• Chemical Name: (3aR,5R,6S,6aR)-5-(azidomethyl)tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxol-6-yl 4-methylbenzenesulfonate
• CAS No.: 172039-03-1
• Molecular Formula: C₁₅H₁₉N₃O₆S
• Molecular Weight: 369.398
• Mol file: 172039-03-1.mol

Synonyms:(3aR,5R,6S,6aR)-5-(azidomethyl)tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxol-6-yl 4-methylbenzenesulfonate

Chemical Property of (3aR,5R,6S,6aR)-5-(azidomethyl)tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxol-6-yl 4-methylbenzenesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,5R,6S,6aR)-5-(azidomethyl)tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxol-6-yl 4-methylbenzenesulfonate

There total 4 articles about (3aR,5R,6S,6aR)-5-(azidomethyl)tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxol-6-yl 4-methylbenzenesulfonate 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: 98.0%

2,2-dimethyl-6-(4-methylphenylsulfonyloxymethyl)-5-(4-methylphenylsulfonyloxymethyl)-(3aR,5R,6S,6aR)-perhydrofuro[2,3-d][1,3]dioxole (4119-18-0,7010-99-3,7061-63-4,55073-85-3) → (3aR,5R,6S,6aR)-5-(azidomethyl)tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxol-6-yl 4-methylbenzenesulfonate (172039-03-1)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 120 ℃; for 2h;

DOI:10.1016/0008-6215(95)00110-F

Reference yield: 92.0%

5-azido-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose (4711-03-9) + p-toluenesulfonyl chloride (98-59-9) → (3aR,5R,6S,6aR)-5-(azidomethyl)tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxol-6-yl 4-methylbenzenesulfonate (172039-03-1)

Guidance literature:

With pyridine; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1002/chem.201500127

Reference yield:

1,2-O-isopropylidene-α-D-xylose (20031-21-4) → 5-azido-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose (4711-03-9) + (3aR,5R,6S,6aR)-5-(azidomethyl)tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxol-6-yl 4-methylbenzenesulfonate (172039-03-1)

Guidance literature:

With pyridine; sodium azide; water; p-toluenesulfonyl chloride; urea; Yield given. Yields of byproduct given; Ambient temperature; 1.) room temperature, 2.) DMF, 110 deg C, 20 h;

DOI:10.1135/cccc19961027

upstream raw materials:

2,2-dimethyl-6-(4-methylphenylsulfonyloxymethyl)-5-(4-methylphenylsulfonyloxymethyl)-(3aR,5R,6S,6aR)-perhydrofuro[2,3-d][1,3]dioxole

1,2-O-isopropylidene-α-D-xylose

p-toluenesulfonyl chloride

5-azido-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose

Downstream raw materials:

1,2-di-O-acetyl-5-azido-5-deoxy-3-O-p-toluenesulfonyl-D-xylofuranose

1-(5-azido-5-deoxy-3-O-p-toluenesulfonyl-β-D-xylofuranosyl)-5-fluorouracil

1-(2-O-acetyl-5-azido-5-deoxy-3-O-p-toluenesulfonyl-β-D-xylofuranosyl)thymine

1-(2-O-acetyl-5-azido-5-deoxy-3-O-p-toluenesulfonyl-β-D-xylofuranosyl)-5-fluorouracil