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

Base Information

• Chemical Name: 6,6'-diazido-2,3,4,2',3',4'-hexa-O-benzyl-6,6'-dideoxy-α,α-trehalose
• CAS No.: 76790-47-1
• Molecular Formula: C₅₄H₅₆N₆O₉
• Molecular Weight: 933.073
• Mol file: 76790-47-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about 6,6'-diazido-2,3,4,2',3',4'-hexa-O-benzyl-6,6'-dideoxy-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: 93.0%

2,3,4,2',3',4'-hexa-O-benzyl-6,6'-di-O-(methylsulfonyl)-α,α-trehalose (74512-35-9) → 6,6'-diazido-2,3,4,2',3',4'-hexa-O-benzyl-6,6'-dideoxy-α,α-trehalose (76790-47-1)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 130 - 135 ℃; for 15h;

DOI:10.1016/S0008-6215(00)85200-3

Reference yield:

2,3,4-tri-O-benzyl-6-O-trifluoromethylsulfonyl-α-D-glucopyranosyl 2,3,4-tri-O-benzyl-6-O-trifluoromethylsulfonyl-α-D-glucopyranoside (129729-12-0) → 6,6'-diazido-2,3,4,2',3',4'-hexa-O-benzyl-6,6'-dideoxy-α,α-trehalose (76790-47-1)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; for 12h;

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'-diazido-2,3,4,2',3',4'-hexa-O-benzyl-6,6'-dideoxy-α,α-trehalose (76790-47-1)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / CH₂Cl₂ / 0.5 h

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

With pyridine; sodium azide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2004.09.033

upstream raw materials:

2,3,4,2',3',4'-hexa-O-benzyl-6,6'-di-O-(methylsulfonyl)-α,α-trehalose

2,3,4-tri-O-benzyl-6-O-trifluoromethylsulfonyl-α-D-glucopyranosyl 2,3,4-tri-O-benzyl-6-O-trifluoromethylsulfonyl-α-D-glucopyranoside

[(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

Downstream raw materials:

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

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

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

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