3-[(benzyloxycarbonyl)amino]propyl 3,4,6-tri-O-acetyl-2-O-[4,6-di-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-2-O-benzoyl-α-D-mannopyranosyl]-α-D-mannopyranoside

Base Information

Chemical Name:3-[(benzyloxycarbonyl)amino]propyl 3,4,6-tri-O-acetyl-2-O-[4,6-di-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-2-O-benzoyl-α-D-mannopyranosyl]-α-D-mannopyranoside
CAS No.:866029-11-0
Molecular Formula:C₅₄H₆₇NO₂₈
Molecular Weight:1178.12
Hs Code.:

3-[(benzyloxycarbonyl)amino]propyl 3,4,6-tri-O-acetyl-2-O-[4,6-di-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-2-O-benzoyl-α-D-mannopyranosyl]-α-D-mannopyranoside

Synonyms:3-[(benzyloxycarbonyl)amino]propyl 3,4,6-tri-O-acetyl-2-O-[4,6-di-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-2-O-benzoyl-α-D-mannopyranosyl]-α-D-mannopyranoside

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Chemical Property of 3-[(benzyloxycarbonyl)amino]propyl 3,4,6-tri-O-acetyl-2-O-[4,6-di-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-2-O-benzoyl-α-D-mannopyranosyl]-α-D-mannopyranoside

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Technology Process of 3-[(benzyloxycarbonyl)amino]propyl 3,4,6-tri-O-acetyl-2-O-[4,6-di-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-2-O-benzoyl-α-D-mannopyranosyl]-α-D-mannopyranoside

There total 7 articles about 3-[(benzyloxycarbonyl)amino]propyl 3,4,6-tri-O-acetyl-2-O-[4,6-di-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-2-O-benzoyl-α-D-mannopyranosyl]-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: 91.0%

: 866029-09-6
3,4,6-tri-O-acetyl-2-O-[4,6-di-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-2-O-benzoyl-α-D-mannopyranosyl]-1-O-trichloroacetimidoyl-α-D-mannopyranose

: 34637-22-4
3-[(N-benzyloxycarbonyl)amino]propanol

: 866029-11-0
3-[(benzyloxycarbonyl)amino]propyl 3,4,6-tri-O-acetyl-2-O-[4,6-di-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-2-O-benzoyl-α-D-mannopyranosyl]-α-D-mannopyranoside

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 - 10 ℃; for 1.5h;
DOI:10.1002/ejoc.200500146

Reference yield:

: 866029-00-7
4,6-di-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-2-O-benzoyl-α-D-mannopyranose

: 866029-11-0
3-[(benzyloxycarbonyl)amino]propyl 3,4,6-tri-O-acetyl-2-O-[4,6-di-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-2-O-benzoyl-α-D-mannopyranosyl]-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 79 percent / DBU / CH₂Cl₂ / 1 h / -5 °C

2: 55 percent / BF₃*OEt₂ / CH₂Cl₂ / 0.5 h / 0 - 10 °C

3: 85 percent / NH₂NH₂*HOAc / dimethylformamide / 2 h / 20 °C

4: 89 percent / K₂CO₃ / CH₂Cl₂ / 2 h / 20 °C

5: 91 percent / TMSOTf / CH₂Cl₂ / 1.5 h / 0 - 10 °C

With trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; hydrazinium monoacetate; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.200500146

Reference yield:

: 866028-98-0
1,4,6-tri-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-2-O-benzoyl-α-D-mannopyranose

: 866029-11-0
3-[(benzyloxycarbonyl)amino]propyl 3,4,6-tri-O-acetyl-2-O-[4,6-di-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-2-O-benzoyl-α-D-mannopyranosyl]-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 93 percent / NH₂NH₂*HOAc / dimethylformamide / 4 h / 20 °C

2: 79 percent / DBU / CH₂Cl₂ / 1 h / -5 °C

3: 55 percent / BF₃*OEt₂ / CH₂Cl₂ / 0.5 h / 0 - 10 °C

4: 85 percent / NH₂NH₂*HOAc / dimethylformamide / 2 h / 20 °C

5: 89 percent / K₂CO₃ / CH₂Cl₂ / 2 h / 20 °C

6: 91 percent / TMSOTf / CH₂Cl₂ / 1.5 h / 0 - 10 °C

With trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; hydrazinium monoacetate; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.200500146