benzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranoside

Base Information

• Chemical Name: benzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranoside
• CAS No.: 41355-94-6
• Molecular Formula: C₂₁H₂₇NO₉
• Molecular Weight: 437.447
• Mol file: 41355-94-6.mol

Synonyms:benzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranoside

Chemical Property of benzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranoside

There total 66 articles about benzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranoside 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: 97.0%

(3R,4R,5R,6R)-3-acetamido-6-(acetoxymethyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate (76375-60-5) + benzyl alcohol (100-51-6,185532-71-2) → benzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranoside (41355-94-6)

Guidance literature:

With ytterbium(III) triflate; In dichloromethane; at 60 ℃; stereoselective reaction;

DOI:10.1021/acs.joc.6b02929

Reference yield: 95.0%

2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranosyl acetate (3006-60-8,4539-83-7,6730-10-5,7772-79-4,7784-54-5,10385-50-9,26151-16-6,76375-60-5,76375-61-6,95341-98-3,95341-99-4,134451-91-5,134451-96-0,136982-81-5,145375-11-7,148347-15-3,14086-90-9) + benzyl alcohol (100-51-6,185532-71-2) → benzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside (10375-65-2,13318-46-2,13343-66-3,19374-72-2,33423-34-6,34029-78-2,41355-94-6,110911-57-4,141019-71-8)

Guidance literature:

With ytterbium(III) triflate; In dichloromethane; at 60 ℃; stereoselective reaction;

DOI:10.1021/acs.joc.6b02929

Reference yield: 93.0%

benzyl alcohol (100-51-6,185532-71-2) + 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) → benzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside (10375-65-2,13318-46-2,13343-66-3,19374-72-2,33423-34-6,34029-78-2,41355-94-6,110911-57-4,141019-71-8)

Guidance literature:

With iron(III) trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1039/c7ob01201b

upstream raw materials:

acetic anhydride

benzyl 3,4,6-tri-O-acetyl-2-amino-2-deoxy-β-D-glucopyranoside

benzyl alcohol

2-acetylamino-3,4,6-triacetyl-2-deoxy-α-D-glucopyranosyl bromide

Downstream raw materials:

benzyl 3,4,6-tri-O-acetyl-2-acetylamino-2-deoxy-α-D-glucopyranoside

C₂₅H₃₁NO₇

deprotected 9

C₃₀H₄₆N₂O₁₂Si