2-(benzyloxycarbonyl)aminoethyl 3,4-di-O-acetyl-2-azido-6-O-(tert-butyldimethylsilyl)-2-deoxy-α-D-mannopyranoside

Base Information

• Chemical Name: 2-(benzyloxycarbonyl)aminoethyl 3,4-di-O-acetyl-2-azido-6-O-(tert-butyldimethylsilyl)-2-deoxy-α-D-mannopyranoside
• CAS No.: 870074-00-3
• Molecular Formula: C₂₆H₄₀N₄O₉Si
• Molecular Weight: 580.711
• Mol file: 870074-00-3.mol

Synonyms:2-(benzyloxycarbonyl)aminoethyl 3,4-di-O-acetyl-2-azido-6-O-(tert-butyldimethylsilyl)-2-deoxy-α-D-mannopyranoside

Chemical Property of 2-(benzyloxycarbonyl)aminoethyl 3,4-di-O-acetyl-2-azido-6-O-(tert-butyldimethylsilyl)-2-deoxy-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(benzyloxycarbonyl)aminoethyl 3,4-di-O-acetyl-2-azido-6-O-(tert-butyldimethylsilyl)-2-deoxy-α-D-mannopyranoside

There total 5 articles about 2-(benzyloxycarbonyl)aminoethyl 3,4-di-O-acetyl-2-azido-6-O-(tert-butyldimethylsilyl)-2-deoxy-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: 86.0%

ethyl 3,4-di-O-acetyl-2-azido-6-O-(tert-butyldimethylsilyl)-2-deoxy-1-thio-α-D-mannopyranoside (870073-99-7) + benzyl 2-hydroxyethylcarbamate (77987-49-6) → 2-(benzyloxycarbonyl)aminoethyl 3,4-di-O-acetyl-2-azido-6-O-(tert-butyldimethylsilyl)-2-deoxy-α-D-mannopyranoside (870074-00-3)

Guidance literature:

With N-iodo-succinimide; 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; for 0.5h;

DOI:10.1039/b507898a

Reference yield:

(2R,3S,4R,5S,6R)-5-Azido-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-ethylsulfanyl-tetrahydro-pyran-3,4-diol → 2-(benzyloxycarbonyl)aminoethyl 3,4-di-O-acetyl-2-azido-6-O-(tert-butyldimethylsilyl)-2-deoxy-α-D-mannopyranoside (870074-00-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / 4 Angstroem molecular sieves; N-iodosuccinimide; AgOTf / CH₂Cl₂ / 0.5 h

With N-iodo-succinimide; 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane;

DOI:10.1039/b507898a

Reference yield:

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-D-mannopyranoside (68733-20-0) → 2-(benzyloxycarbonyl)aminoethyl 3,4-di-O-acetyl-2-azido-6-O-(tert-butyldimethylsilyl)-2-deoxy-α-D-mannopyranoside (870074-00-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 68 percent / 4 Angstroem molecular sieves; BF₃*OEt₂ / CH₂Cl₂ / 7 h

2: NaOMe / methanol / 1 h

3: pyridine / 20 °C

4: 86 percent / 4 Angstroem molecular sieves; N-iodosuccinimide; AgOTf / CH₂Cl₂ / 0.5 h

With pyridine; N-iodo-succinimide; 4 A molecular sieve; boron trifluoride diethyl etherate; sodium methylate; silver trifluoromethanesulfonate; In methanol; dichloromethane;

DOI:10.1039/b507898a

upstream raw materials:

ethyl 3,4-di-O-acetyl-2-azido-6-O-(tert-butyldimethylsilyl)-2-deoxy-1-thio-α-D-mannopyranoside

benzyl 2-hydroxyethylcarbamate

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

ethyl 2-azido-2-deoxy-1-thio-α-D-mannopyranoside

Downstream raw materials:

2-(benzyloxycarbonyl)aminoethyl 3,4-di-O-acetyl-2-azido-2-deoxy-α-D-mannopyranoside