4-methylphenyl 2-azido-3,4-O-isopropylidene-2-deoxy-1-thio-β-D-galactopyranoside

Base Information

• Chemical Name: 4-methylphenyl 2-azido-3,4-O-isopropylidene-2-deoxy-1-thio-β-D-galactopyranoside
• CAS No.: 875484-86-9
• Molecular Formula: C₁₆H₂₁N₃O₄S
• Molecular Weight: 351.426
• Mol file: 875484-86-9.mol

Synonyms:4-methylphenyl 2-azido-3,4-O-isopropylidene-2-deoxy-1-thio-β-D-galactopyranoside

Chemical Property of 4-methylphenyl 2-azido-3,4-O-isopropylidene-2-deoxy-1-thio-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-methylphenyl 2-azido-3,4-O-isopropylidene-2-deoxy-1-thio-β-D-galactopyranoside

There total 1 articles about 4-methylphenyl 2-azido-3,4-O-isopropylidene-2-deoxy-1-thio-β-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: 39.0%

2,2-dimethoxy-propane (77-76-9) + p-methylphenyl 2-deoxy-2-azido-1-thio-β-D-galactopyranoside (125760-22-7) → 4-methylphenyl 2-azido-3,4-O-isopropylidene-2-deoxy-1-thio-β-D-galactopyranoside (875484-86-9)

Guidance literature:

With toluene-4-sulfonic acid; In acetonitrile; for 2h;

DOI:10.1016/j.carres.2005.11.010

Reference yield: 86.0%

4-methylphenyl 2-azido-3,4-O-isopropylidene-2-deoxy-1-thio-β-D-galactopyranoside (875484-86-9) + 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside (3068-32-4) → 4-methylphenyl-2-azido-3,4-O-isopropylidene-2-deoxy-6-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-1-thio-β-D-galactopyranoside (875484-87-0)

Guidance literature:

With 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; toluene; at -40 - -30 ℃;

DOI:10.1016/j.carres.2005.11.010

Reference yield:

4-methylphenyl 2-azido-3,4-O-isopropylidene-2-deoxy-1-thio-β-D-galactopyranoside (875484-86-9) → (2S,3R)-3-[(2S,3R,4R,5R,6R)-3-Azido-4,5-dihydroxy-6-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid 2-oxo-2-phenyl-ethyl ester

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / 4 Angstroem molecular sieves; silver triflate / toluene; CH₂Cl₂ / -40 - -30 °C

2: 56 percent / 4 Angstroem molecular sieves; DMTST / CH₂Cl₂; diethyl ether; toluene / 5 h / 20 °C

3: aq. AcOH / 2 h / 90 °C

With 4 A molecular sieve; silver trifluoromethanesulfonate; acetic acid; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; In diethyl ether; dichloromethane; toluene;

DOI:10.1016/j.carres.2005.11.010

upstream raw materials:

2,2-dimethoxy-propane

p-methylphenyl 2-deoxy-2-azido-1-thio-β-D-galactopyranoside

Downstream raw materials:

4-methylphenyl-2-azido-3,4-O-isopropylidene-2-deoxy-6-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-1-thio-β-D-galactopyranoside

N-(9-fluorenylmethyloxycarbonyl)-O-[2-azido-3,4-O-isopropylidene-2-deoxy-6-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-threonine phenacylester

N-(9-fluorenylmethyloxycarbonyl)-O-[2-acetamido-3,4-di-O-acetyl-2-deoxy-6-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-threonine phenacylester