4,6-O-benzylidene-β-D-galactopyranosyl azide

Base Information

• Chemical Name: 4,6-O-benzylidene-β-D-galactopyranosyl azide
• CAS No.: 204510-86-1
• Molecular Formula: C₁₃H₁₅N₃O₅
• Molecular Weight: 293.279
• Mol file: 204510-86-1.mol

Synonyms:4,6-O-benzylidene-β-D-galactopyranosyl azide

Chemical Property of 4,6-O-benzylidene-β-D-galactopyranosyl azide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4,6-O-benzylidene-β-D-galactopyranosyl azide

There total 4 articles about 4,6-O-benzylidene-β-D-galactopyranosyl azide 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%

1-amido-1-deoxygalactopyranose (35899-89-9) + benzaldehyde dimethyl acetal (1125-88-8) → 4,6-O-benzylidene-β-D-galactopyranosyl azide (204510-86-1)

Guidance literature:

With toluene-4-sulfonic acid; In acetonitrile;

DOI:10.1016/S0040-4039(03)00475-1

Reference yield: 64.0%

benzaldehyde dimethyl acetal (1125-88-8) + (2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-azidotetrahydro-2H-pyran-3,4,5-triyl triacetate (13992-26-2) → 4,6-O-benzylidene-β-D-galactopyranosyl azide (204510-86-1)

Guidance literature:

(2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-azidotetrahydro-2H-pyran-3,4,5-triyl triacetate; With sodium methylate; In methanol; at 20 ℃; for 1h;

benzaldehyde dimethyl acetal; With toluene-4-sulfonic acid; In acetonitrile; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1039/c2cc37067k

Reference yield:

(2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-azidotetrahydro-2H-pyran-3,4,5-triyl triacetate (13992-26-2) → 4,6-O-benzylidene-β-D-galactopyranosyl azide (204510-86-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / NaOMe / methanol / 0.5 h

2: 81 percent / p-TsOH / acetonitrile / 24 h / 20 °C

With sodium methylate; toluene-4-sulfonic acid; In methanol; acetonitrile;

DOI:10.1002/chem.200400042

upstream raw materials:

1-amido-1-deoxygalactopyranose

benzaldehyde dimethyl acetal

(2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-azidotetrahydro-2H-pyran-3,4,5-triyl triacetate

β-D-galactose peracetate

Downstream raw materials:

(2S,4aR,6R,7R,8S,8aS)-6-Azido-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

C₂₇H₂₃N₃O₇

(S)-4,6-O-benzylidene-3-O-(N-benzoylcarbamoyl)-galactopyranosyl azide

(R)-4,6-O-benzylidene-talopyranosyl azide