N-benzyloxycarbonyl-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-L-serine myristylamide

Base Information

• Chemical Name: N-benzyloxycarbonyl-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-L-serine myristylamide
• CAS No.: 171191-22-3
• Molecular Formula: C₃₉H₆₀N₂O₁₃
• Molecular Weight: 764.911
• Mol file: 171191-22-3.mol

Synonyms:N-benzyloxycarbonyl-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-L-serine myristylamide

Chemical Property of N-benzyloxycarbonyl-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-L-serine myristylamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-benzyloxycarbonyl-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-L-serine myristylamide

There total 3 articles about N-benzyloxycarbonyl-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-L-serine myristylamide 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: 77.0%

2,3,4,6-tetra-O-acetyl-d-glucopyranosyl trichloroacetimidate (74808-10-9,86520-63-0,87119-53-7,92052-29-4,121238-27-5,127061-80-7,142831-80-9) + N-benzyloxycarbonyl-L-serine myristylamide (171191-19-8) → N-benzyloxycarbonyl-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-L-serine myristylamide (171191-22-3)

Guidance literature:

With 4 A molecular sieve; boron trifluoride diethyl etherate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; Ambient temperature;

DOI:10.1248/cpb.43.594

Reference yield:

tetradecylamine (2016-42-4) → N-benzyloxycarbonyl-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-L-serine myristylamide (171191-22-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / Et₃N / CH₂Cl₂ / 5 h / Ambient temperature

2: 77 percent / 1,8-diazabicyclo<5.4.0>-7-undecene, BF₃*OEt₂, 4 A molecular sieves / CH₂Cl₂ / Ambient temperature

With 4 A molecular sieve; boron trifluoride diethyl etherate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In dichloromethane;

DOI:10.1248/cpb.43.594

Reference yield:

N-carbobenzoxy-L-serine-2,4-dinitrophenol (5249-65-0) → N-benzyloxycarbonyl-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-L-serine myristylamide (171191-22-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / Et₃N / CH₂Cl₂ / 5 h / Ambient temperature

2: 77 percent / 1,8-diazabicyclo<5.4.0>-7-undecene, BF₃*OEt₂, 4 A molecular sieves / CH₂Cl₂ / Ambient temperature

With 4 A molecular sieve; boron trifluoride diethyl etherate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In dichloromethane;

DOI:10.1248/cpb.43.594

upstream raw materials:

2,3,4,6-tetra-O-acetyl-d-glucopyranosyl trichloroacetimidate

N-benzyloxycarbonyl-L-serine myristylamide

tetradecylamine

N-carbobenzoxy-L-serine-2,4-dinitrophenol