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

Base Information

• Chemical Name: N-<4-trans-N-(benzyloxycarbonylamino)methylcyclohexylcarbonyl>-β-D-mannopyranosylamine
• CAS No.: 74761-65-2
• Molecular Formula: C₂₂H₃₂N₂O₈
• Molecular Weight: 452.505
• Mol file: 74761-65-2.mol

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

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

There total 5 articles about 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: 89.0%

2,3,4,6-tetra-O-acetyl-N-<4-trans-N-(benzyloxycarbonylamino)methylcyclohexylcarbonyl>-β-D-mannopyranosylamine (74761-76-5) → N-<4-trans-N-(benzyloxycarbonylamino)methylcyclohexylcarbonyl>-β-D-mannopyranosylamine (74761-65-2)

Guidance literature:

With sodium methylate; In methanol;

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

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) → N-<4-trans-N-(benzyloxycarbonylamino)methylcyclohexylcarbonyl>-β-D-mannopyranosylamine (74761-65-2)

Guidance literature:

Multi-step reaction with 4 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

4: 89 percent / sodium methoxide / methanol

With dmap; hydrogen; sodium methylate; tin(IV) chloride; nickel; In methanol; 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) → N-<4-trans-N-(benzyloxycarbonylamino)methylcyclohexylcarbonyl>-β-D-mannopyranosylamine (74761-65-2)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 89 percent / sodium methoxide / methanol

With dmap; hydrogen; sodium methylate; nickel; In methanol; dichloromethane; ethyl acetate;

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

upstream raw materials:

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

D-Mannose pentaacetate

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

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

Downstream raw materials:

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