N-(2,3,4,6-Tetra-O-acetyl-D-galactopyranosyloxycarbonyl)-L-phenylalanyl-L-serine tert-butyl ester

Base Information

• Chemical Name: N-(2,3,4,6-Tetra-O-acetyl-D-galactopyranosyloxycarbonyl)-L-phenylalanyl-L-serine tert-butyl ester
• CAS No.: 312933-67-8
• Molecular Formula: C₃₁H₄₂N₂O₁₅
• Molecular Weight: 682.679

Synonyms:N-(2,3,4,6-Tetra-O-acetyl-D-galactopyranosyloxycarbonyl)-L-phenylalanyl-L-serine tert-butyl ester

Chemical Property of N-(2,3,4,6-Tetra-O-acetyl-D-galactopyranosyloxycarbonyl)-L-phenylalanyl-L-serine tert-butyl ester

Chemical Property:

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Technology Process of N-(2,3,4,6-Tetra-O-acetyl-D-galactopyranosyloxycarbonyl)-L-phenylalanyl-L-serine tert-butyl ester

There total 1 articles about N-(2,3,4,6-Tetra-O-acetyl-D-galactopyranosyloxycarbonyl)-L-phenylalanyl-L-serine tert-butyl 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: 40.0%

tert-butyl (2S)-2-amino-3-hydroxypropanoate (90048-49-0,851588-08-4) + N-(2,3,4,6-Tetra-O-acetyl-D-galactopyranosyloxycarbonyl)-L-phenylalanine → N-(2,3,4,6-Tetra-O-acetyl-D-galactopyranosyloxycarbonyl)-L-phenylalanyl-L-serine tert-butyl ester (312933-67-8)

Guidance literature:

With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; In dichloromethane; at 20 ℃;

DOI:10.1002/1521-3765(20001016)6:20<3714::AID-CHEM3714>3.0.CO;2-Z

Reference yield:

N-(2,3,4,6-Tetra-O-acetyl-D-galactopyranosyloxycarbonyl)-L-phenylalanyl-L-serine tert-butyl ester (312933-67-8) → (S)-3-Hydroxy-2-[(S)-3-phenyl-2-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxycarbonylamino)-propionylamino]-propionic acid tert-butyl ester

Guidance literature:

With phosphate buffer; lipase WG; In acetone; at 37 ℃; for 72h; Enzymatic reaction;

DOI:10.1002/1521-3765(20001016)6:20<3714::AID-CHEM3714>3.0.CO;2-Z

Reference yield:

N-(2,3,4,6-Tetra-O-acetyl-D-galactopyranosyloxycarbonyl)-L-phenylalanyl-L-serine tert-butyl ester (312933-67-8) → L-Phenylalanine-L-serine tert-butyl ester

Guidance literature:

Multi-step reaction with 2 steps

1: lipase WG; aq. phosphate buffer / acetone / 72 h / 37 °C / Enzymatic reaction

2: β-galactosidase; aq. phosphate buffer / acetone / 24 h / 37 °C / Enzymatic reaction

With phosphate buffer; lipase WG; β-galactosidase; In acetone; 1: Deacetylation / 2: Hydrolysis;

DOI:10.1002/1521-3765(20001016)6:20<3714::AID-CHEM3714>3.0.CO;2-Z

upstream raw materials:

tert-butyl (2S)-2-amino-3-hydroxypropanoate

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