2-isopropyl-4,5-(4,6-O-benzylidene-1,2-dideoxy-α-D-glucopyrano)-[2,1-d]-2-oxazoline

Base Information

• Chemical Name: 2-isopropyl-4,5-(4,6-O-benzylidene-1,2-dideoxy-α-D-glucopyrano)-[2,1-d]-2-oxazoline
• CAS No.: 225796-46-3
• Molecular Formula: C₁₇H₂₁NO₅
• Molecular Weight: 319.357
• Mol file: 225796-46-3.mol

Synonyms:2-isopropyl-4,5-(4,6-O-benzylidene-1,2-dideoxy-α-D-glucopyrano)-[2,1-d]-2-oxazoline

Chemical Property of 2-isopropyl-4,5-(4,6-O-benzylidene-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-isopropyl-4,5-(4,6-O-benzylidene-1,2-dideoxy-α-D-glucopyrano)-[2,1-d]-2-oxazoline

There total 5 articles about 2-isopropyl-4,5-(4,6-O-benzylidene-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: 73.0%

Acetic acid (3aR,4aR,7R,8aS,9R,9aR)-2-isopropyl-7-phenyl-3a,4a,5,8a,9,9a-hexahydro-3,4,6,8-tetraoxa-1-aza-cyclopenta[b]naphthalen-9-yl ester (225796-45-2) → 2-isopropyl-4,5-(4,6-O-benzylidene-1,2-dideoxy-α-D-glucopyrano)-[2,1-d]-2-oxazoline (225796-46-3)

Guidance literature:

With potassium carbonate; In methanol; for 1h; Ambient temperature;

DOI:10.1039/a810041a

Reference yield:

Acetic acid (2R,4aR,7R,8R,8aS)-6-acetoxy-7-isobutyrylamino-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (225796-44-1) → 2-isopropyl-4,5-(4,6-O-benzylidene-1,2-dideoxy-α-D-glucopyrano)-[2,1-d]-2-oxazoline (225796-46-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 52 percent / SnCl₄ / CH₂Cl₂ / 2 h / 20 °C

2: 73 percent / potassium carbonate / methanol; CHCl₃ / 1 h / 20 °C

With tin(IV) chloride; potassium carbonate; In methanol; dichloromethane; chloroform; 1: Cyclization / 2: Deacetylation;

DOI:10.1021/jo990901u

Reference yield:

(+)-D-glucosamine hydrochloride (1078691-95-8) → 2-isopropyl-4,5-(4,6-O-benzylidene-1,2-dideoxy-α-D-glucopyrano)-[2,1-d]-2-oxazoline (225796-46-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 86 percent / sodium methoxide / methanol / 24 h / 20 °C

2: ZnCl₂ / 6 h / 20 °C

3: pyridine / 24 h / 20 °C

4: 52 percent / SnCl₄ / CH₂Cl₂ / 2 h / 20 °C

5: 73 percent / potassium carbonate / methanol; CHCl₃ / 1 h / 20 °C

With pyridine; sodium methylate; tin(IV) chloride; potassium carbonate; zinc(II) chloride; In methanol; dichloromethane; chloroform; 1: Acylation / 2: Cyclization / 3: Acetylation / 4: Cyclization / 5: Deacetylation;

DOI:10.1021/jo990901u

upstream raw materials:

Acetic acid (3aR,4aR,7R,8aS,9R,9aR)-2-isopropyl-7-phenyl-3a,4a,5,8a,9,9a-hexahydro-3,4,6,8-tetraoxa-1-aza-cyclopenta[b]naphthalen-9-yl ester

(+)-D-glucosamine hydrochloride

N-isopropyl-D-glucosamine

Acetic acid (2R,4aR,7R,8R,8aS)-6-acetoxy-7-isobutyrylamino-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Downstream raw materials:

C₄₅H₆₀NO₇P

C₃₉H₄₈NO₉P