N-(benzyloxycarbonyl)-O-(β-D-galactopyranosyl)-(1->3)-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-(1->3)-L-serine allyl ester

Base Information

• Chemical Name: N-(benzyloxycarbonyl)-O-(β-D-galactopyranosyl)-(1->3)-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-(1->3)-L-serine allyl ester
• CAS No.: 188641-26-1
• Molecular Formula: C₂₈H₄₀N₂O₁₅
• Molecular Weight: 644.63
• Mol file: 188641-26-1.mol

Synonyms:N-(benzyloxycarbonyl)-O-(β-D-galactopyranosyl)-(1->3)-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-(1->3)-L-serine allyl ester

Chemical Property of N-(benzyloxycarbonyl)-O-(β-D-galactopyranosyl)-(1->3)-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-(1->3)-L-serine allyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(benzyloxycarbonyl)-O-(β-D-galactopyranosyl)-(1->3)-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-(1->3)-L-serine allyl ester

There total 6 articles about N-(benzyloxycarbonyl)-O-(β-D-galactopyranosyl)-(1->3)-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-(1->3)-L-serine allyl 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%

N-(benzyloxycarbonyl)-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-(1->3)-L-serine allyl ester (188641-24-9) + 4-nitrophenyl-β-D-galactopyranoside (3150-24-1) → N-(benzyloxycarbonyl)-O-(β-D-galactopyranosyl)-(1->3)-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-(1->3)-L-serine allyl ester (188641-26-1)

Guidance literature:

With KPB buffer; In N,N-dimethyl-formamide; at 37 ℃; for 4.5h; in the presence of β1-3 galactosidase from Bacillus circulans;

DOI:10.1016/S0040-4039(97)00019-1

Reference yield: 68.0%

N-(benzyloxycarbonyl)-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-(1->3)-L-serine allyl ester (188641-24-9) + 4-Nitro-benzoic acid (2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl ester → N-(benzyloxycarbonyl)-O-(β-D-galactopyranosyl)-(1->3)-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-(1->3)-L-serine allyl ester (188641-26-1)

Guidance literature:

With potassium phosphate buffer; recombinant β(1,3)-galactosidase from B. curculans; In N,N-dimethyl-formamide; at 37 ℃; for 4.5h; pH=6.0;

DOI:10.1081/CAR-120003741

Reference yield:

3-O-(2-Acetamido-2-desoxy-α-D-galactopyranosyl)-L-serin (17041-36-0,72259-90-6,116949-18-9,67262-86-6) → N-(benzyloxycarbonyl)-O-(β-D-galactopyranosyl)-(1->3)-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-(1->3)-L-serine allyl ester (188641-26-1)

Guidance literature:

Multi-step reaction with 3 steps

1: aq. NaOH / 10 h / 0 °C

2: 4.83 g / Et₃N / dimethylformamide / 20 h / 20 °C

3: 68 percent / recombinant β(1,3)-galactosidase from B. curculans; potassium phosphate buffer / dimethylformamide / 4.5 h / 37 °C / pH 6.0

With sodium hydroxide; potassium phosphate buffer; recombinant β(1,3)-galactosidase from B. curculans; triethylamine; In N,N-dimethyl-formamide;

DOI:10.1081/CAR-120003741

upstream raw materials:

N-(benzyloxycarbonyl)-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-(1->3)-L-serine allyl ester

4-nitrophenyl-β-D-galactopyranoside

benzyl chloroformate

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

Downstream raw materials:

N-(benzyloxycarbonyl)-O-(3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->3)-O-(2-acetamido-2-deoxy-4,6-O-isopropylidene-α-D-galactopyranosyl)-(1->3)-L-serine allyl ester

N-(benzyloxycarbonyl)-O-(β-D-galactopyranosyl)-(1->3)-O-[(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-3-nonulopyranosylonic acid)-(2->6)]-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-(1->3)-L-serine