phenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-seleno-α-L-galactopyranoside

Base Information

• Chemical Name: phenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-seleno-α-L-galactopyranoside
• CAS No.: 849222-00-0
• Molecular Formula: C₁₈H₂₁N₃O₇Se
• Molecular Weight: 470.341
• Mol file: 849222-00-0.mol

Synonyms:phenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-seleno-α-L-galactopyranoside

Chemical Property of phenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-seleno-α-L-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-seleno-α-L-galactopyranoside

There total 3 articles about phenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-seleno-α-L-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: 61.0%

3,4,6-tri-O-acetyl-L-galactal (849221-99-4) + diphenyl diselenide (1666-13-3) → phenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-seleno-α-L-galactopyranoside (849222-00-0)

Guidance literature:

With sodium azide; [bis(acetoxy)iodo]benzene; In dichloromethane; for 18h;

DOI:10.1002/chem.200400862

Reference yield:

Acetic acid (2S,3R,4R,5S)-3,5-diacetoxy-2-acetoxymethyl-6-bromo-tetrahydro-pyran-4-yl ester (138514-71-3) → phenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-seleno-α-L-galactopyranoside (849222-00-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 3.12 g / CuSO₄; Zn; aq. NaOAc / CH₂Cl₂ / 3 h / -10 °C

2: 61 percent / NaN₃; bisacetoxyiodobenzene / CH₂Cl₂ / 18 h

With sodium azide; [bis(acetoxy)iodo]benzene; sodium acetate; copper(II) sulfate; zinc; In dichloromethane;

DOI:10.1002/chem.200400862

Reference yield:

1,2,3,4,6-penta-O-acetyl-α,β-L-galactose (70749-17-6) → phenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-seleno-α-L-galactopyranoside (849222-00-0)

Guidance literature:

Multi-step reaction with 3 steps

1: HBr; AcOH / 1,2-dichloro-ethane / 3 h / 0 °C

2: 3.12 g / CuSO₄; Zn; aq. NaOAc / CH₂Cl₂ / 3 h / -10 °C

3: 61 percent / NaN₃; bisacetoxyiodobenzene / CH₂Cl₂ / 18 h

With sodium azide; [bis(acetoxy)iodo]benzene; hydrogen bromide; sodium acetate; copper(II) sulfate; acetic acid; zinc; In dichloromethane; 1,2-dichloro-ethane;

DOI:10.1002/chem.200400862

upstream raw materials:

3,4,6-tri-O-acetyl-L-galactal

diphenyl diselenide

Acetic acid (2S,3R,4R,5S)-3,5-diacetoxy-2-acetoxymethyl-6-bromo-tetrahydro-pyran-4-yl ester

1,2,3,4,6-penta-O-acetyl-α,β-L-galactose

Downstream raw materials:

methyl 4-O-acetyl-2-azido-6-O-tert-butyldiphenylsilyl-2-deoxy-β-L-galactopyranoside

methyl 4-O-acetyl-2-azido-3-O-{2-azido-3-O-benzyl-4-O-(3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-6-O-tert-butyldimethylsilyl-2-deoxy-β-D-mannopyranosyl}-6-O-tert-butyldiphenylsilyl-2-deoxy-β-L-galactopyranoside

methyl 2-acetamido-4-O-acetyl-3-O-{2-acetamido-3-O-benzyl-4-O-(2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-6-O-tert-butyldimethylsilyl-2-deoxy-β-D-mannopyranosyl}-6-O-tert-butyldiphenylsilyl-2-deoxy-β-L-galactopyranoside

methyl 4-O-acetyl-2-azido-3-O-{2-azido-3-O-benzyl-4-O-(2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-6-O-tert-butyldimethylsilyl-2-deoxy-β-D-mannopyranosyl}-6-O-tert-butyldiphenylsilyl-2-deoxy-β-L-galactopyranoside