benzyl O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-serinate

Base Information

• Chemical Name: benzyl O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-serinate
• CAS No.: 100929-00-8
• Molecular Formula: C₃₇H₃₈N₄O₁₂
• Molecular Weight: 730.728

Synonyms:benzyl O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-serinate

Chemical Property of benzyl O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-serinate

Chemical Property:

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Technology Process of benzyl O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-serinate

There total 31 articles about benzyl O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-serinate 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-(9-fluorenylmethyloxycarbonyl)-L-serine benzyl ester (118358-66-0,73724-46-6) + 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl iodide (68733-27-7) → benzyl O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-serinate (100929-00-8)

Guidance literature:

With 4 A molecular sieve; iodine; In dichloromethane;

DOI:10.1081/CAR-200067028

Reference yield: 72.0%

3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-galactopyranosyl trichloroacetimidate (167939-15-3) + N-(9-fluorenylmethyloxycarbonyl)-L-serine benzyl ester (118358-66-0,73724-46-6) → benzyl O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-serinate (100929-00-8)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In diethyl ether; dichloromethane; at -30 ℃; for 0.5h;

DOI:10.1016/j.carres.2006.02.013

Reference yield: 65.0%

3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl chloride (67817-37-2) + N-(9-fluorenylmethyloxycarbonyl)-L-serine benzyl ester (118358-66-0,73724-46-6) → N-(9-fluorenylmethyloxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl)-L-serine benzyl ester + benzyl O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-serinate (100929-00-8)

Guidance literature:

With silver (I) ion;

upstream raw materials:

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

N-(9-fluorenylmethyloxycarbonyl)-L-serine benzyl ester

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

acetic anhydride

Downstream raw materials:

benzyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-serinate

N,O-diacetyl-L-seryl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galctopyranosyl)-L-seryl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-threonine benzylester

C₄₅H₆₃N₅O₂₃

O-allyl-N-<2-(4-pyridyl)ethoxycarbonyl>-L-tyrosyl-L-isoleucyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-serine benzyl ester

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