2,3,4,6-tetra-O-acetyl-N-<4-trans-N-(benzyloxycarbonylamino)methylcyclohexylcarbonyl>-β-D-mannopyranosylamine

Base Information

• Chemical Name: 2,3,4,6-tetra-O-acetyl-N-<4-trans-N-(benzyloxycarbonylamino)methylcyclohexylcarbonyl>-β-D-mannopyranosylamine
• CAS No.: 74761-76-5
• Molecular Formula: C₃₀H₄₀N₂O₁₂
• Molecular Weight: 620.654
• Mol file: 74761-76-5.mol

Synonyms:2,3,4,6-tetra-O-acetyl-N-<4-trans-N-(benzyloxycarbonylamino)methylcyclohexylcarbonyl>-β-D-mannopyranosylamine

Chemical Property of 2,3,4,6-tetra-O-acetyl-N-<4-trans-N-(benzyloxycarbonylamino)methylcyclohexylcarbonyl>-β-D-mannopyranosylamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3,4,6-tetra-O-acetyl-N-<4-trans-N-(benzyloxycarbonylamino)methylcyclohexylcarbonyl>-β-D-mannopyranosylamine

There total 3 articles about 2,3,4,6-tetra-O-acetyl-N-<4-trans-N-(benzyloxycarbonylamino)methylcyclohexylcarbonyl>-β-D-mannopyranosylamine 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:

D-Mannose pentaacetate (83-87-4,604-68-2,604-69-3,2152-77-4,4026-35-1,4163-59-1,4163-60-4,4163-61-5,4163-65-9,4257-94-7,4257-96-9,16299-15-3,19186-39-1,19189-55-0,25878-60-8,25941-03-1,32445-48-0,32445-49-1,32445-53-7,32445-54-8,34685-58-0,34685-59-1,43168-42-9,43168-44-1,43169-22-8,43169-25-1,66966-07-2,70749-17-6,80184-01-6,93221-01-3,93221-02-4,99630-88-3,109215-53-4,115792-70-6,115792-73-9,139894-92-1,139973-25-4,144071-49-8,147648-81-5) → 2,3,4,6-tetra-O-acetyl-N-<4-trans-N-(benzyloxycarbonylamino)methylcyclohexylcarbonyl>-β-D-mannopyranosylamine (74761-76-5)

Guidance literature:

Multi-step reaction with 3 steps

1: stannic tetrachloride / CH₂Cl₂ / 6 h

2: 61 percent / H₂ / Raney nickel / ethyl acetate / 6.5 h

3: 1.7 g / 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / Ambient temperature

With dmap; hydrogen; tin(IV) chloride; nickel; In dichloromethane; ethyl acetate;

DOI:10.1016/S0008-6215(00)85529-9

Reference yield:

2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl azide (53784-29-5) → 2,3,4,6-tetra-O-acetyl-N-<4-trans-N-(benzyloxycarbonylamino)methylcyclohexylcarbonyl>-β-D-mannopyranosylamine (74761-76-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 61 percent / H₂ / Raney nickel / ethyl acetate / 6.5 h

2: 1.7 g / 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / Ambient temperature

With dmap; hydrogen; nickel; In dichloromethane; ethyl acetate;

DOI:10.1016/S0008-6215(00)85529-9

Reference yield:

1-amino-2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl (41355-50-4) + trans-4-(N-carbobenzyloxy)aminomethyl-1-cyclohexane carbonyl chloride (27687-13-4) → 2,3,4,6-tetra-O-acetyl-N-<4-trans-N-(benzyloxycarbonylamino)methylcyclohexylcarbonyl>-β-D-mannopyranosylamine (74761-76-5)

Guidance literature:

With dmap; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1016/S0008-6215(00)85529-9

upstream raw materials:

1-amino-2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl

trans-4-(N-carbobenzyloxy)aminomethyl-1-cyclohexane carbonyl chloride

D-Mannose pentaacetate

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

Downstream raw materials:

N-<4-trans-N-(benzyloxycarbonylamino)methylcyclohexylcarbonyl>-β-D-mannopyranosylamine

N-<4-trans-(aminomethyl)cyclohexylcarbonyl>-β-D-mannopyranosylamine