O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-benzyloxycarbonyl-L-serine benzyl ester

Base Information

• Chemical Name: O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-benzyloxycarbonyl-L-serine benzyl ester
• CAS No.: 83956-33-6
• Molecular Formula: C₃₀H₃₄N₄O₁₂
• Molecular Weight: 642.62
• Mol file: 83956-33-6.mol

Synonyms:O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-benzyloxycarbonyl-L-serine benzyl ester

Chemical Property of O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-benzyloxycarbonyl-L-serine benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-benzyloxycarbonyl-L-serine benzyl ester

There total 6 articles about O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-benzyloxycarbonyl-L-serine benzyl ester 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%

N-(Benzyloxycarbonyl)-L-serin-benzylester (21209-51-8) + Ethyl-3,4,6-tri-O-acetyl-2-azido-2-desoxy-1-thio-β-D-galactopyranosid (110797-30-3) → N-(Benzyloxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-azido-2-desoxy-β-D-galactopyranosyl)-L-serin-benzylester (110797-32-5) + N-(Benzyloxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-azido-2-desoxy-α-D-galactopyranosyl)-L-serin-benzylester (83956-33-6)

Guidance literature:

With dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; In dichloromethane; toluene; for 12h; Yield given. Title compound not separated from byproducts;

Reference yield: 54.0%

N-benzyloxycarbonyl-L-serine benzyl ester (21209-51-8) + 3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl trichloroacetimidate (83025-11-0) → O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-benzyloxycarbonyl-L-serine benzyl ester (83956-33-6)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -15 - 20 ℃; for 0.5h;

DOI:10.1016/S0008-6215(96)00324-2

Reference yield: 44.0%

N-benzyloxycarbonyl-L-serine benzyl ester (21209-51-8) + phenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thiol-D-galactopyranoside (197663-12-0) → (S)-2-Benzyloxycarbonylamino-3-((2R,3R,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-propionic acid benzyl ester (110797-32-5) + O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-benzyloxycarbonyl-L-serine benzyl ester (83956-33-6)

Guidance literature:

N-benzyloxycarbonyl-L-serine benzyl ester; phenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thiol-D-galactopyranoside; In dichloromethane; at 20 ℃; for 0.5h; Inert atmosphere; Molecular sieve;

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1021/acs.orglett.5b00512

upstream raw materials:

N-benzyloxycarbonyl-L-serine benzyl ester

3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-galactopyranosyl trichloroacetimidate

Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-azido-6-(pyridin-2-ylsulfanylcarbonyloxy)-tetrahydro-pyran-4-yl ester

3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl trichloroacetimidate

Downstream raw materials:

3-O-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-N-(benzyloxycarbonyl)-L-serinbenzylester

3-O-(2-acetamido-2-deoxy-3-O-β-D-galactopyranosyl-α-D-galactopyranosyl)-L-serine

3-O-(2-Acetamido-2-desoxy-α-D-galactopyranosyl)-L-serin