6,6'-dideoxy-6,6'-di(monobromoacetyl)amino-2,2',3,3',4,4'-hexa-O-benzyl-α-D-trehalose

Base Information

• Chemical Name: 6,6'-dideoxy-6,6'-di(monobromoacetyl)amino-2,2',3,3',4,4'-hexa-O-benzyl-α-D-trehalose
• CAS No.: 827026-06-2
• Molecular Formula: C₅₈H₆₂Br₂N₂O₁₁
• Molecular Weight: 1122.95
• Mol file: 827026-06-2.mol

Synonyms:6,6'-dideoxy-6,6'-di(monobromoacetyl)amino-2,2',3,3',4,4'-hexa-O-benzyl-α-D-trehalose

Chemical Property of 6,6'-dideoxy-6,6'-di(monobromoacetyl)amino-2,2',3,3',4,4'-hexa-O-benzyl-α-D-trehalose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6,6'-dideoxy-6,6'-di(monobromoacetyl)amino-2,2',3,3',4,4'-hexa-O-benzyl-α-D-trehalose

There total 4 articles about 6,6'-dideoxy-6,6'-di(monobromoacetyl)amino-2,2',3,3',4,4'-hexa-O-benzyl-α-D-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: 74.0%

bromoacetic acid (79-08-3) + 6,6'-diamino-2,3,4,2',3',4'-hexa-O-benzyl-6,6'-dideoxy-α,α-trehalose (76790-48-2) → 6,6'-dideoxy-6,6'-di(monobromoacetyl)amino-2,2',3,3',4,4'-hexa-O-benzyl-α-D-trehalose (827026-06-2)

Guidance literature:

With diisopropyl-carbodiimide; In N,N-dimethyl-formamide; at 20 ℃; for 4h;

DOI:10.1016/j.bmc.2004.09.033

Reference yield:

[(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl]-methanol (125177-97-1,128188-35-2,74501-33-0) → 6,6'-dideoxy-6,6'-di(monobromoacetyl)amino-2,2',3,3',4,4'-hexa-O-benzyl-α-D-trehalose (827026-06-2)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / CH₂Cl₂ / 0.5 h

2: 0.78 g / sodium azide / dimethylformamide / 12 h

3: 76 percent / trimethylphosphine; sodium hydroxide / tetrahydrofuran / 3 h / 50 °C

4: 74 percent / diisopropylcarbodiimide / dimethylformamide / 4 h / 20 °C

With pyridine; sodium hydroxide; sodium azide; diisopropyl-carbodiimide; trimethylphosphane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2004.09.033

Reference yield:

6,6'-diazido-2,3,4,2',3',4'-hexa-O-benzyl-6,6'-dideoxy-α,α-trehalose (76790-47-1) → 6,6'-dideoxy-6,6'-di(monobromoacetyl)amino-2,2',3,3',4,4'-hexa-O-benzyl-α-D-trehalose (827026-06-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / trimethylphosphine; sodium hydroxide / tetrahydrofuran / 3 h / 50 °C

2: 74 percent / diisopropylcarbodiimide / dimethylformamide / 4 h / 20 °C

With sodium hydroxide; diisopropyl-carbodiimide; trimethylphosphane; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2004.09.033

upstream raw materials:

bromoacetic acid

6,6'-diamino-2,3,4,2',3',4'-hexa-O-benzyl-6,6'-dideoxy-α,α-trehalose

[(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl]-methanol

6,6'-diazido-2,3,4,2',3',4'-hexa-O-benzyl-6,6'-dideoxy-α,α-trehalose

Downstream raw materials:

6,6'-dideoxy-6,6'-di(monoheptaminoacetyl)amino-2,2',3,3',4,4'-hexa-O-benzyl-α-D-trehalose