N-allyl-N-[5-(1,2-dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-4-methyl-benzenesulfonamide

Base Information

• Chemical Name: N-allyl-N-[5-(1,2-dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-4-methyl-benzenesulfonamide
• CAS No.: 252053-08-0
• Molecular Formula: C₁₉H₂₇NO₇S
• Molecular Weight: 413.492
• Mol file: 252053-08-0.mol

Synonyms:N-allyl-N-[5-(1,2-dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-4-methyl-benzenesulfonamide

Chemical Property of N-allyl-N-[5-(1,2-dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-4-methyl-benzenesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-allyl-N-[5-(1,2-dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-4-methyl-benzenesulfonamide

There total 4 articles about N-allyl-N-[5-(1,2-dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-4-methyl-benzenesulfonamide 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: 90.0%

3-deoxy-3-(N-allyl-p-toluenesulphonamido)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (252053-00-2) → N-allyl-N-[5-(1,2-dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-4-methyl-benzenesulfonamide (252053-08-0)

Guidance literature:

With acetic acid; at 20 ℃; for 14h;

DOI:10.1016/S0040-4020(99)00694-8

Reference yield:

p-toluenesulfonyl chloride (98-59-9) → N-allyl-N-[5-(1,2-dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-4-methyl-benzenesulfonamide (252053-08-0)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / 16 h / 25 °C

2: K₂CO₃ / acetone / 24 h / 25 °C

3: 90 percent / aq. acetic acid / 14 h / 20 °C

With pyridine; potassium carbonate; acetic acid; In acetone; 1: Tosylation / 2: Alkylation / 3: Hydrolysis;

DOI:10.1016/S0040-4020(99)00694-8

Reference yield:

3-amino-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (16848-19-4,24384-84-7,71165-01-0,71187-80-9,73881-34-2,91067-83-3) → N-allyl-N-[5-(1,2-dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-4-methyl-benzenesulfonamide (252053-08-0)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / 16 h / 25 °C

2: K₂CO₃ / acetone / 24 h / 25 °C

3: 90 percent / aq. acetic acid / 14 h / 20 °C

With pyridine; potassium carbonate; acetic acid; In acetone; 1: Tosylation / 2: Alkylation / 3: Hydrolysis;

DOI:10.1016/S0040-4020(99)00694-8

upstream raw materials:

3-deoxy-3-(N-allyl-p-toluenesulphonamido)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

p-toluenesulfonyl chloride

3-amino-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

N-[(3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-4-methyl-benzenesulfonamide

Downstream raw materials:

(5aS,6R,7R,8aR)-1-benzyl-5-p-toluenesulphonyl-1,3,3a,5a,6,7,8a,8b-octahydro-6,7-isopropylidenedioxy-4H-furo[2',3':5,6]pyrido[4,3-c]isoxazole

N-Allyl-N-((3aR,5S,6S,6aR)-5-formyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl)-4-methyl-benzenesulfonamide