2,3,4,2',3',4',6'-hepta-O-acetyl-6-bromo-6-deoxy-α,α-trehalose

Base Information

• Chemical Name: 2,3,4,2',3',4',6'-hepta-O-acetyl-6-bromo-6-deoxy-α,α-trehalose
• CAS No.: 42891-35-0
• Molecular Formula: C₂₆H₃₅BrO₁₇
• Molecular Weight: 699.458
• Mol file: 42891-35-0.mol

Synonyms:

Chemical Property of 2,3,4,2',3',4',6'-hepta-O-acetyl-6-bromo-6-deoxy-α,α-trehalose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3,4,2',3',4',6'-hepta-O-acetyl-6-bromo-6-deoxy-α,α-trehalose

There total 1 articles about 2,3,4,2',3',4',6'-hepta-O-acetyl-6-bromo-6-deoxy-α,α-trehalose 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: 25.0%

TREHALOSE (99-20-7) + acetic anhydride (108-24-7) → 2,3,4,2',3',4',6'-hepta-O-acetyl-6-bromo-6-deoxy-α,α-trehalose (42891-35-0) + 2,2',3,3',4,4'-hex-O-acetyl-6,6'-dideoxy-6,6'-dibromo-α,α-D-trehalose (42891-34-9) + trehalose octaacetate (25018-27-3)

Guidance literature:

TREHALOSE; With triphenylphosphine; In N,N-dimethyl-formamide; at 20 ℃; for 0.25h; Inert atmosphere;

With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20 - 60 ℃; Inert atmosphere;

acetic anhydride; With pyridine; at 0 - 20 ℃;

DOI:10.1016/j.bmcl.2021.127929

Reference yield:

2,3,4,2',3',4',6'-hepta-O-acetyl-6-bromo-6-deoxy-α,α-trehalose (42891-35-0) → 6-[N-({[(benzyloxy)carbonyl]amino}butanoyl)amino]-6-deoxy-α,α-trehalose (644965-00-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 74 percent / NaN₃ / dimethylformamide / 20 h / 95 °C

2: 78 percent / NaOMe / methanol / 14 h / 20 °C

3: 68 percent / NH₂-NH₂ / Pd(OH)2/C / methanol / 8 h / Heating

4: 61 percent / DCC / methanol; dimethylformamide / 16 h / 20 °C

With sodium azide; sodium methylate; dicyclohexyl-carbodiimide; hydrazine; palladium dihydroxide; In methanol; N,N-dimethyl-formamide;

DOI:10.1002/hlca.200390213

Reference yield:

2,3,4,2',3',4',6'-hepta-O-acetyl-6-bromo-6-deoxy-α,α-trehalose (42891-35-0) → 6-({Nα-[(benzyloxy)carbonyl]-Nω-nitro-L-arginyl}amino)-6-deoxy-α,α-trehalose (644964-99-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 74 percent / NaN₃ / dimethylformamide / 20 h / 95 °C

2: 78 percent / NaOMe / methanol / 14 h / 20 °C

3: 68 percent / NH₂-NH₂ / Pd(OH)2/C / methanol / 8 h / Heating

4: 39 percent / DCC / methanol; dimethylformamide / 16 h / 20 °C

With sodium azide; sodium methylate; dicyclohexyl-carbodiimide; hydrazine; palladium dihydroxide; In methanol; N,N-dimethyl-formamide;

DOI:10.1002/hlca.200390213

upstream raw materials:

TREHALOSE

acetic anhydride

Downstream raw materials:

6-({N-[(benzyloxy)carbonyl]glycyl}amino)-6-deoxy-α,α-trehalos

6-[N-({[(benzyloxy)carbonyl]amino}butanoyl)amino]-6-deoxy-α,α-trehalose

6-({N^α-[(benzyloxy)carbonyl]-N^ω-nitro-L-arginyl}amino)-6-deoxy-α,α-trehalose