[2-(methyl-4-carbamoylbutanoyl)ethyl] (2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-1-thio-α-D-mannopyranoside

Base Information

• Chemical Name: [2-(methyl-4-carbamoylbutanoyl)ethyl] (2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-1-thio-α-D-mannopyranoside
• CAS No.: 904691-53-8
• Molecular Formula: C₄₉H₅₅NO₂₀S
• Molecular Weight: 1010.04
• Mol file: 904691-53-8.mol

Synonyms:[2-(methyl-4-carbamoylbutanoyl)ethyl] (2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-1-thio-α-D-mannopyranoside

Chemical Property of [2-(methyl-4-carbamoylbutanoyl)ethyl] (2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-1-thio-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [2-(methyl-4-carbamoylbutanoyl)ethyl] (2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-1-thio-α-D-mannopyranoside

There total 5 articles about [2-(methyl-4-carbamoylbutanoyl)ethyl] (2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-1-thio-α-D-mannopyranoside 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: 61.0%

4-(2-mercapto-ethylcarbamoyl)-butyric acid methyl ester + (2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-D-mannopyranosyl trichloroacetoimidate → [2-(methyl-4-carbamoylbutanoyl)ethyl] (2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-1-thio-α-D-mannopyranoside (904691-53-8)

Guidance literature:

With molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; at -20 - 0 ℃; for 1h;

DOI:10.1002/anie.200600591

Reference yield:

phenyl (2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-1-thio-α-D-mannopyranoside (904691-50-5) → [2-(methyl-4-carbamoylbutanoyl)ethyl] (2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-1-thio-α-D-mannopyranoside (904691-53-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / NBS / acetone / 1 h / 20 °C

2: 72 percent / DBU / CH₂Cl₂ / 0.5 h / 20 °C

3: 61 percent / molecular sieves; BF₃*Et₂O / CH₂Cl₂ / 1 h / -20 - 0 °C

With N-Bromosuccinimide; molecular sieve; boron trifluoride diethyl etherate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; acetone;

DOI:10.1002/anie.200600591

Reference yield:

2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl trichloroimidate (121238-27-5) → [2-(methyl-4-carbamoylbutanoyl)ethyl] (2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-1-thio-α-D-mannopyranoside (904691-53-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 77 percent / molecular sieves; TMSOTf / CH₂Cl₂ / 0.5 h / -20 - 0 °C

2: 99 percent / NBS / acetone / 1 h / 20 °C

3: 72 percent / DBU / CH₂Cl₂ / 0.5 h / 20 °C

4: 61 percent / molecular sieves; BF₃*Et₂O / CH₂Cl₂ / 1 h / -20 - 0 °C

With N-Bromosuccinimide; molecular sieve; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; acetone;

DOI:10.1002/anie.200600591

upstream raw materials:

phenyl (2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-1-thio-α-D-mannopyranoside

2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl trichloroimidate

phenyl 2,3,4-tri-O-benzoyl-1-thio-α-D-mannopyranoside