(2R,3S,4R,5R,6S)-5-acetamido-2-(acetoxymethyl)-6-(allyloxy)tetrahydro-2H-pyran-3,4-diyl diacetate

Base Information

• Chemical Name: (2R,3S,4R,5R,6S)-5-acetamido-2-(acetoxymethyl)-6-(allyloxy)tetrahydro-2H-pyran-3,4-diyl diacetate
• CAS No.: 63064-48-2
• Molecular Formula: C₁₇H₂₅NO₉
• Molecular Weight: 387.387
• Mol file: 63064-48-2.mol

Synonyms:(2R,3S,4R,5R,6S)-5-acetamido-2-(acetoxymethyl)-6-(allyloxy)tetrahydro-2H-pyran-3,4-diyl diacetate

Chemical Property of (2R,3S,4R,5R,6S)-5-acetamido-2-(acetoxymethyl)-6-(allyloxy)tetrahydro-2H-pyran-3,4-diyl diacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4R,5R,6S)-5-acetamido-2-(acetoxymethyl)-6-(allyloxy)tetrahydro-2H-pyran-3,4-diyl diacetate

There total 40 articles about (2R,3S,4R,5R,6S)-5-acetamido-2-(acetoxymethyl)-6-(allyloxy)tetrahydro-2H-pyran-3,4-diyl diacetate 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: 98.0%

allyl 2-acetamido-2-deoxy-β-D-glucopyranoside (54400-75-8,64650-83-5,88903-97-3,116347-86-5,140849-88-3,144300-01-6,54400-77-0) + acetic anhydride (108-24-7) → allyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside (63064-48-2,116288-58-5,117299-90-8,126778-02-7,28738-44-5)

Guidance literature:

With pyridine; at 0 ℃;

DOI:10.1016/j.bmc.2004.01.013

Reference yield: 85.0%

allyl alcohol (107-18-6) + acetic acid (3aR,5R,6R,7R,7aR)-6-acetoxy-5-acetoxymethyl-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazol-7-yl ester (10378-06-0) → allyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranoside (28738-44-5,63064-48-2,117299-90-8,126778-02-7,116288-58-5)

Guidance literature:

With trifluorormethanesulfonic acid; In dichloromethane; at 70 ℃; for 4h; Molecular sieve; Sealed tube;

DOI:10.1055/s-0036-1591082

Reference yield: 84.0%

allyl alcohol (107-18-6) + 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose (3006-60-8,4539-83-7,6730-10-5,7772-79-4,7784-54-5,10385-50-9,14086-90-9,26151-16-6,76375-60-5,76375-61-6,95341-98-3,95341-99-4,134451-91-5,134451-96-0,136982-81-5,145375-11-7,148347-15-3) → allyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside (63064-48-2,116288-58-5,117299-90-8,126778-02-7,28738-44-5)

Guidance literature:

With camphor-10-sulfonic acid; In benzene; Heating; azeotropic removal of acetic acid;

DOI:10.1016/0040-4039(95)02233-3

upstream raw materials:

acetic anhydride

3,4,6-tetra-O-acetyl-2-deoxy-2-iodo-α-D-mannopyranosyl azide

allyl alcohol

2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline

Downstream raw materials:

3-benzylthiopropyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside

allyl 2-acetamido-(R)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

allyl 2-acetamido-3-O-benzyl-(R)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

(R)-2,3-epoxypropyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside