(2R,3R,4R)-1-Azido-3,4-bis-benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butan-2-ol

Base Information

• Chemical Name: (2R,3R,4R)-1-Azido-3,4-bis-benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butan-2-ol
• CAS No.: 313355-01-0
• Molecular Formula: C₂₃H₂₉N₃O₅
• Molecular Weight: 427.5
• Mol file: 313355-01-0.mol

Synonyms:(2R,3R,4R)-1-Azido-3,4-bis-benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butan-2-ol

Chemical Property of (2R,3R,4R)-1-Azido-3,4-bis-benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R)-1-Azido-3,4-bis-benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butan-2-ol

There total 3 articles about (2R,3R,4R)-1-Azido-3,4-bis-benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butan-2-ol 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: 95.0%

3,4-di-O-benzyl-1,2-O-isopropylidene-6-O-p-toluenesulfonyl-D-mannitol (152310-26-4) → (2R,3R,4R)-1-Azido-3,4-bis-benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butan-2-ol (313355-01-0)

Guidance literature:

With sodium azide; In DMF (N,N-dimethyl-formamide); at 80 ℃; for 3h;

Reference yield:

3,4-di-O-benzyloxy-5,6-O-isopropylidene-D-mannitol (121964-05-4) → (2R,3R,4R)-1-Azido-3,4-bis-benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butan-2-ol (313355-01-0)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N; DMAP / CH₂Cl₂ / 5 h / 0 - 20 °C

2: sodium azide / dimethylformamide / 4 h / 80 °C

With dmap; sodium azide; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2007.07.158

Reference yield:

3,4-di-O-benzyl-1,2:5,6-di-O-isopropylidene-D-mannitol (111476-62-1) → (2R,3R,4R)-1-Azido-3,4-bis-benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butan-2-ol (313355-01-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 66 percent / methanol / Acid hydrolysis

2: Et₃N; DMAP / CH₂Cl₂

3: NaN₃ / dimethylformamide / 80 °C

With dmap; sodium azide; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide; 1: Hydrolysis / 2: Tosylation / 3: Substitution;

DOI:10.1016/S0040-4039(00)01425-8

upstream raw materials:

3,4-di-O-benzyl-1,2-O-isopropylidene-6-O-p-toluenesulfonyl-D-mannitol

3,4-di-O-benzyloxy-5,6-O-isopropylidene-D-mannitol

3,4-di-O-benzyl-1,2:5,6-di-O-isopropylidene-D-mannitol

Downstream raw materials:

6-azido-3,4-di-O-benzyl-6-deoxy-D-mannitol

N-Boc-6-amino-2,5-anhydro-3,4-di-O-benzyl-6-deoxy-D-mannitol

N-Boc-6-amino-2,5-anhydro-3,4-di-O-benzyl-6-deoxy-D-mannonic acid

methyl N-Boc-6-amino-2,5-anhydro-3,4-di-O-benzyl-6-deoxy-D-mannonate