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

Base Information

• Chemical Name: 3-deoxy-3-(N-allyl-p-toluenesulphonamido)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose
• CAS No.: 252053-00-2
• Molecular Formula: C₂₂H₃₁NO₇S
• Molecular Weight: 453.557
• Mol file: 252053-00-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

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

allyl bromide (106-95-6) + 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 (846549-48-2) → 3-deoxy-3-(N-allyl-p-toluenesulphonamido)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (252053-00-2)

Guidance literature:

With potassium carbonate; In acetone; at 25 ℃; for 24h;

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

Reference yield:

p-toluenesulfonyl chloride (98-59-9) → 3-deoxy-3-(N-allyl-p-toluenesulphonamido)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (252053-00-2)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 16 h / 25 °C

2: K₂CO₃ / acetone / 24 h / 25 °C

With pyridine; potassium carbonate; In acetone; 1: Tosylation / 2: Alkylation;

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) → 3-deoxy-3-(N-allyl-p-toluenesulphonamido)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (252053-00-2)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 16 h / 25 °C

2: K₂CO₃ / acetone / 24 h / 25 °C

With pyridine; potassium carbonate; In acetone; 1: Tosylation / 2: Alkylation;

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

upstream raw materials:

allyl bromide

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

p-toluenesulfonyl chloride

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

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

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