2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->3)-2-azide-4,6-O-benzylidene-2-deoxy-β-D-galactopyranosyl fluoride

Base Information

• Chemical Name: 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->3)-2-azide-4,6-O-benzylidene-2-deoxy-β-D-galactopyranosyl fluoride
• CAS No.: 186972-19-0
• Molecular Formula: C₂₇H₃₂FN₃O₁₃
• Molecular Weight: 625.562
• Mol file: 186972-19-0.mol

Synonyms:2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->3)-2-azide-4,6-O-benzylidene-2-deoxy-β-D-galactopyranosyl fluoride

Chemical Property of 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->3)-2-azide-4,6-O-benzylidene-2-deoxy-β-D-galactopyranosyl fluoride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->3)-2-azide-4,6-O-benzylidene-2-deoxy-β-D-galactopyranosyl fluoride

There total 10 articles about 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->3)-2-azide-4,6-O-benzylidene-2-deoxy-β-D-galactopyranosyl fluoride 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: 87.0%

2,3,4,6-tetra-O-acetyl-D-galactopyranosyl trichloroacetimidate (74808-10-9,86520-63-0,87119-53-7,92052-29-4,121238-27-5,142831-80-9,127061-80-7) + 2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranosyl fluoride (165397-89-7) → 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->3)-2-azide-4,6-O-benzylidene-2-deoxy-β-D-galactopyranosyl fluoride (186972-19-0)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at -15 ℃; for 2h;

DOI:10.1016/S0040-4020(02)01359-5

Reference yield: 81.0%

2,3,4,6-tetra-O-acetyl-D-galactopyranosyl trichloroacetimidate (74808-10-9,86520-63-0,87119-53-7,92052-29-4,121238-27-5,142831-80-9,127061-80-7) + (2S,4aR,7R,8R,8aR)-7-Azido-6-fluoro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol (186972-18-9) → 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->3)-2-azide-4,6-O-benzylidene-2-deoxy-β-D-galactopyranosyl fluoride (186972-19-0)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -20 ℃; for 1.5h;

DOI:10.1039/cc9960002779

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->3)-2-azide-4,6-O-benzylidene-2-deoxy-β-D-galactopyranosyl fluoride (186972-19-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.51 g / camphorsulfonic acid / dimethylformamide / 2 h / 50 °C

2: 87 percent / trimethylsilyl trifluoromethanesulfonate; molecular sieves 4 Angstroem / CH₂Cl₂ / 2 h / -15 °C

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; camphor-10-sulfonic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(02)01359-5

upstream raw materials:

2,3,4,6-tetra-O-acetyl-D-galactopyranosyl trichloroacetimidate

(2S,4aR,7R,8R,8aR)-7-Azido-6-fluoro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranosyl fluoride

benzaldehyde dimethyl acetal

Downstream raw materials:

C₅₂H₆₂N₆O₂₀

(2R,3R,4S,5R,6R)-2-((2S,4aR,6S,7R,8R,8aR)-7-Azido-6-fluoro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

C₅₄H₆₆N₄O₂₁