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

Base Information

• Chemical Name: N-trichloroethoxycarbonyl-3-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-serine benzyl ester
• CAS No.: 197663-14-2
• Molecular Formula: C₂₇H₃₃Cl₃N₂O₁₃
• Molecular Weight: 699.924
• Mol file: 197663-14-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about N-trichloroethoxycarbonyl-3-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-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: 68.0%

tiolacetic acid (507-09-5) + N-trichloroethoxycarbonyl-3-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-L-serine benzyl ester (197663-13-1) → N-trichloroethoxycarbonyl-3-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-serine benzyl ester (197663-14-2)

Guidance literature:

With pyridine; In dichloromethane; for 4h; Ambient temperature;

DOI:10.1248/cpb.45.1544

Reference yield:

benzyl N-(2,2,2-trichloroethoxycarbonyl)-L-serine (82911-81-7) → N-trichloroethoxycarbonyl-3-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-serine benzyl ester (197663-14-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / NBS, I₂, tetrabutylammonium trifluoromethanesulfonate, 4A molecular sieves / diethyl ether / a) -20 deg C, 1 h, b) RT, 2 h

2: 68 percent / pyridine / CH₂Cl₂ / 8 h / Ambient temperature

With pyridine; N-Bromosuccinimide; 4 A molecular sieve; iodine; tetrabutylammonium trifluoromethylsulfonate; In diethyl ether; dichloromethane;

DOI:10.1248/cpb.46.1676

Reference yield:

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-galactopyranose (84278-00-2) → N-trichloroethoxycarbonyl-3-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-serine benzyl ester (197663-14-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / BF₃*Et₂O / CH₂Cl₂ / 4 h / Ambient temperature

2: 65 percent / N-bromosuccinimide, I₂, tetrabutylammonium trifluoromethanesulfonate / diethyl ether / 2 h / Ambient temperature

3: 68 percent / pyridine / CH₂Cl₂ / 4 h / Ambient temperature

With pyridine; N-Bromosuccinimide; boron trifluoride diethyl etherate; iodine; tetrabutylammonium trifluoromethylsulfonate; In diethyl ether; dichloromethane;

DOI:10.1248/cpb.45.1544

upstream raw materials:

tiolacetic acid

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

benzyl N-(2,2,2-trichloroethoxycarbonyl)-L-serine

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-galactopyranose

Downstream raw materials:

N-trichloroethoxycarbonyl-3-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-seryl-(N'-benzyloxycarbonylaminoethyl)amide

N-acetyl-3-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-serine-(N'-benzyloxycarbonylaminoethyl)amide

N-acetyl-3-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-serine-(N'-benzyloxycarbonylaminoethyl)amide