methyl N-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyloxycarbonyl)-L-phenylalaninate

Base Information

• Chemical Name: methyl N-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyloxycarbonyl)-L-phenylalaninate
• CAS No.: 1428318-20-0
• Molecular Formula: C₄₅H₄₇NO₉
• Molecular Weight: 745.869

Synonyms:methyl N-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyloxycarbonyl)-L-phenylalaninate

Chemical Property of methyl N-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyloxycarbonyl)-L-phenylalaninate

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Technology Process of methyl N-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyloxycarbonyl)-L-phenylalaninate

There total 1 articles about methyl N-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyloxycarbonyl)-L-phenylalaninate 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: 75.0%

(S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester (51987-73-6) + 1-deoxy-2,3,4.6-tetrakis-O-phenylmethyl-1-phenylsulfinyl-mannopyranose (325126-12-3) → methyl N-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyloxycarbonyl)-L-phenylalaninate (1428318-20-0)

Guidance literature:

1-deoxy-2,3,4.6-tetrakis-O-phenylmethyl-1-phenylsulfinyl-mannopyranose; With 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; In dichloromethane; at 20 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

(S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester; With trifluoromethylsulfonic anhydride; In dichloromethane; at -70 - -25 ℃; for 18h; Inert atmosphere;

DOI:10.1055/s-0032-1316820

Reference yield: 89.0%

methyl N-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyloxycarbonyl)-L-phenylalaninate (1428318-20-0) → N-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyloxycarbonyl)-L-phenylalanine (1428318-21-1)

Guidance literature:

With lithium hydroxide; In 1,4-dioxane; water; at 8 ℃; for 3h;

DOI:10.1055/s-0032-1316820

Reference yield: 64.0%

methyl N-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyloxycarbonyl)-L-phenylalaninate (1428318-20-0) → methyl N-(α-D-mannopyranosyloxycarbonyl)-L-phenylalaninate (1428318-22-2)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 12h;

DOI:10.1055/s-0032-1316820

upstream raw materials:

(S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester

1-deoxy-2,3,4.6-tetrakis-O-phenylmethyl-1-phenylsulfinyl-mannopyranose

Downstream raw materials:

N-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyloxycarbonyl)-L-phenylalanine

methyl N-(α-D-mannopyranosyloxycarbonyl)-L-phenylalaninate

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