(1R,2R,3R,4S,6R)-4-Azido-1,2-di-O-benzyl-6-<(benzyloxy)methyl>-1,2,3-cyclohexanetriol

Base Information

• Chemical Name: (1R,2R,3R,4S,6R)-4-Azido-1,2-di-O-benzyl-6-<(benzyloxy)methyl>-1,2,3-cyclohexanetriol
• CAS No.: 166376-48-3
• Molecular Formula: C₂₈H₃₁N₃O₄
• Molecular Weight: 473.572
• Mol file: 166376-48-3.mol

Synonyms:(1R,2R,3R,4S,6R)-4-Azido-1,2-di-O-benzyl-6-<(benzyloxy)methyl>-1,2,3-cyclohexanetriol

Chemical Property of (1R,2R,3R,4S,6R)-4-Azido-1,2-di-O-benzyl-6-<(benzyloxy)methyl>-1,2,3-cyclohexanetriol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R,3R,4S,6R)-4-Azido-1,2-di-O-benzyl-6-<(benzyloxy)methyl>-1,2,3-cyclohexanetriol

There total 1 articles about (1R,2R,3R,4S,6R)-4-Azido-1,2-di-O-benzyl-6-<(benzyloxy)methyl>-1,2,3-cyclohexanetriol 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:

(1R,2R,3S,4R,5R)-3,4-di-O-benzyl-5-benzyloxymethyl-1,2-O,O-sulfonyl-cyclohexane-1,2,3,4-tetraol (151693-59-3) → (1R,2R,3S,4R,6R)-3-Azido-1,2-di-O-benzyl-6-<(benzyloxy)methyl>-1,2,4-cyclohexanetriol + (1R,2R,3R,4S,6R)-4-Azido-1,2-di-O-benzyl-6-<(benzyloxy)methyl>-1,2,3-cyclohexanetriol (166376-48-3)

Guidance literature:

With lithium azide; sulfuric acid; Yield given. Multistep reaction. Yields of byproduct given; 1.) DMF, 105 deg C, 2.5 h, 2.) THF, 50 deg C, 30 min;

DOI:10.1021/jo00121a065

Reference yield: 98.0%

acetic anhydride (108-24-7) + (1R,2R,3R,4S,6R)-4-Azido-1,2-di-O-benzyl-6-<(benzyloxy)methyl>-1,2,3-cyclohexanetriol (166376-48-3) → (1R,2R,3R,4S,6R)-3-O-Acetyl-4-azido-1,2-di-O-benzyl-6-<(benzyloxy)methyl>-1,2,3-cyclohexanetriol

Guidance literature:

With pyridine; dmap; In dichloromethane; for 24h; Ambient temperature;

DOI:10.1021/jo00121a065

Reference yield: 96.0%

trifluoromethylsulfonic anhydride (358-23-6) + (1R,2R,3R,4S,6R)-4-Azido-1,2-di-O-benzyl-6-<(benzyloxy)methyl>-1,2,3-cyclohexanetriol (166376-48-3) → (1R,2R,3R,4S,6R)-4-Azido-1,2-di-O-benzyl-6-<(benzyloxy)methyl>-3-O-(trifluoromethylsulfonyl)-1,2,3-cyclohexanetriol (166376-50-7)

Guidance literature:

With pyridine; In dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1021/jo00121a065

upstream raw materials:

(1R,2R,3S,4R,5R)-3,4-di-O-benzyl-5-benzyloxymethyl-1,2-O,O-sulfonyl-cyclohexane-1,2,3,4-tetraol

Downstream raw materials:

(1R,2R,3R,4S,6R)-4-Azido-1,2-di-O-benzyl-6-<(benzyloxy)methyl>-3-O-(trifluoromethylsulfonyl)-1,2,3-cyclohexanetriol

validamine

2-epi-Validamine

(1R,2R,3S,4S,6R)-4-Azido-1,2-di-O-benzyl-6-<(benzyloxy)methyl>-1,2,3-cyclohexanetriol