Phenyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-galactopyranoside

Base Information

• Chemical Name: Phenyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-galactopyranoside
• CAS No.: 153808-91-4
• Molecular Formula: C₃₃H₃₃N₃O₄Se
• Molecular Weight: 614.603
• Mol file: 153808-91-4.mol

Synonyms:Phenyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-galactopyranoside

Chemical Property of Phenyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Phenyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-galactopyranoside

There total 8 articles about Phenyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-galactopyranoside 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: 75.0%

N-phenylselanylphthalimide (71098-88-9) + 3,4,6-tri-O-benzyl-D-galactal (80040-79-5) → Phenyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-galactopyranoside (153808-91-4)

Guidance literature:

With trimethylsilylazide; tetrabutyl ammonium fluoride; In dichloromethane; for 48h; Ambient temperature;

DOI:10.1021/jo00105a051

Reference yield: 72.0%

diphenyl diselenide (1666-13-3) + 3,4,6-tri-O-benzyl-D-galactal (80040-79-5) → Phenyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-galactopyranoside (153808-91-4)

Guidance literature:

With [bis(acetoxy)iodo]benzene; trimethylsilylazide; In dichloromethane; at -30 - -10 ℃; for 2.5h;

DOI:10.1016/j.tetlet.2004.10.022

Reference yield:

triacetyl-D-galactal (4098-06-0) → Phenyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-galactopyranoside (153808-91-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / sodium azide, (diacetoxyiodo)benzene / CH₂Cl₂ / 48 h / Ambient temperature

2: MeONa / methanol / 15 h / Ambient temperature

3: 1.) NaH / 1.) DMF, 0 deg C, 1 h, 2.) DMF, RT, 15 h

With sodium azide; [bis(acetoxy)iodo]benzene; sodium methylate; sodium hydride; In methanol; dichloromethane;

DOI:10.1139/v95-046

upstream raw materials:

N-phenylselanylphthalimide

3,4,6-tri-O-benzyl-D-galactal

benzyl bromide

phenyl 2-azido-2-deoxy-1-seleno-α-D-galactopyranoside

Downstream raw materials:

2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-galactopyranose

Phenyl 2-(N-acetylamino)-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-galactopyranoside

phenyl-2-amino-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-galactopyranoside

2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl fluoride