2-methyl-(3,4,6-tri-O-benzyl-1,2-dideoxy-α-D-glucopyrano)-<2,1-d>-2-oxazoline

Base Information

• Chemical Name: 2-methyl-(3,4,6-tri-O-benzyl-1,2-dideoxy-α-D-glucopyrano)-<2,1-d>-2-oxazoline
• CAS No.: 65372-02-3
• Molecular Formula: C₂₉H₃₁NO₅
• Molecular Weight: 473.569
• Mol file: 65372-02-3.mol

Synonyms:2-methyl-(3,4,6-tri-O-benzyl-1,2-dideoxy-α-D-glucopyrano)-<2,1-d>-2-oxazoline

Chemical Property of 2-methyl-(3,4,6-tri-O-benzyl-1,2-dideoxy-α-D-glucopyrano)-<2,1-d>-2-oxazoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-methyl-(3,4,6-tri-O-benzyl-1,2-dideoxy-α-D-glucopyrano)-<2,1-d>-2-oxazoline

There total 36 articles about 2-methyl-(3,4,6-tri-O-benzyl-1,2-dideoxy-α-D-glucopyrano)-<2,1-d>-2-oxazoline 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: 92.0%

2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl diethyl phosphite + 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (4064-06-6) → O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (66080-60-2) + 2-methyl-(3,4,6-tri-O-benzyl-1,2-dideoxy-α-D-glucopyrano)-<2,1-d>-2-oxazoline (65372-02-3)

Guidance literature:

With bis(trifluoromethanesulfonyl)amide; In dichloromethane; at -78 ℃; for 1h; Inert atmosphere; Molecular sieve;

DOI:10.1021/acs.joc.5b00138

Reference yield: 83.0%

2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl diethyl phosphite + methyl 9-hydroxynonanoate (34957-73-8) → methyl 9-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)oxynonanoate + 2-methyl-(3,4,6-tri-O-benzyl-1,2-dideoxy-α-D-glucopyrano)-<2,1-d>-2-oxazoline (65372-02-3)

Guidance literature:

With bis(trifluoromethanesulfonyl)amide; In dichloromethane; at -78 ℃; for 1h; Inert atmosphere; Molecular sieve;

DOI:10.1021/acs.joc.5b00138

Reference yield: 80.0%

N-(3,4,6-tri-O-benzyl-2-deoxy-2-iodo-α-D-mannopyranosyl)acetamide → (3aS,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-<(benzyloxy)-methyl>-2-methyl-5H-pyrano<2,3-d>oxazole (133004-71-4) + 2-methyl-(3,4,6-tri-O-benzyl-1,2-dideoxy-α-D-glucopyrano)-<2,1-d>-2-oxazoline (65372-02-3)

Guidance literature:

With water; silver trifluoromethanesulfonate; In acetonitrile; at 20 ℃; for 12h; stereoselective reaction;

DOI:10.1002/ejoc.201500001

upstream raw materials:

1-chloro-N-acetyl-3,4,6-tri-O-benzyl-α-D-glucosamine

1-propenyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside

isopropyl alcohol

2-acetamido-1,5-anhydro-1-azi-3,4,6-tri-O-benzyl-2-deoxy-D-glucitol

Downstream raw materials:

2-acetamido-1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-glucitol

3,4,6-tri-O-benzyl-2-acetamido-2-deoxyamino-α-D-glucopyranose

O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose