tetrahydro-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[2,1-d]-1,3-oxazol-2-one

Base Information

• Chemical Name: tetrahydro-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[2,1-d]-1,3-oxazol-2-one
• CAS No.: 76548-23-7
• Molecular Formula: C₁₃H₁₇NO₉
• Molecular Weight: 331.279

Synonyms:tetrahydro-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[2,1-d]-1,3-oxazol-2-one

Chemical Property of tetrahydro-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[2,1-d]-1,3-oxazol-2-one

Chemical Property:

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Technology Process of tetrahydro-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[2,1-d]-1,3-oxazol-2-one

There total 40 articles about tetrahydro-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[2,1-d]-1,3-oxazol-2-one 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: 91.0%

methanol (67-56-1) + 3,4,6-tri-O-acetyl-2-N-allyloxycarbonyl-2-amino-2-deoxy-α-D-glucopyranosyl bromide (104655-87-0) → methyl 3,4,6-tri-O-acetyl-2-N-allyloxycarbonyl-2-amino-2-deoxy-β-D-glucopyranoside (104655-88-1) + tetrahydro-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[2,1-d]-1,3-oxazol-2-one (76548-23-7,10163-09-4)

Guidance literature:

With mercury(II) cyanide; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1016/S0040-4039(00)84594-3

Reference yield: 88.0%

2-(acetoxymethyl)-5-{[(benzyloxy)carbonyl]amino}tetrahydropyran-3,4,6-triyl triacetate (35946-66-8) + benzyl 2-hydroxyethylcarbamate (77987-49-6) → 2-(benzyloxycarbonylamino)ethyl 3,4,6-tri-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-β-D-glucopyranoside (851445-28-8) + tetrahydro-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[2,1-d]-1,3-oxazol-2-one (76548-23-7,10163-09-4)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -15 ℃; for 3h;

DOI:10.1016/j.tetlet.2006.01.137

Reference yield: 88.0%

phosgene (75-44-5) + 3,4,6-tri-O-acetyl-2-amino-2-deoxy-α-D-glucopyranose hydrobromide → tetrahydro-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[2,1-d]-1,3-oxazol-2-one (76548-23-7,10163-09-4)

Guidance literature:

With sodium carbonate; In chloroform; water; toluene; for 12h;

DOI:10.1002/ejoc.200500601

upstream raw materials:

2-(acetoxymethyl)-5-{[(benzyloxy)carbonyl]amino}tetrahydropyran-3,4,6-triyl triacetate

(2R,3S,4R,5R,6R)-2-(acetoxymethyl)-5-(((benzyloxy)carbonyl)amino)-6-chlorotetrahydro-2H-pyran-3,4-diyl diacetate

methanol

3,4,6-tri-O-acetyl-2-N-allyloxycarbonyl-2-amino-2-deoxy-α-D-glucopyranosyl bromide

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