4-methylphenyl 2-azido-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-1-thio-β-D-galactopyranoside

Base Information

• Chemical Name: 4-methylphenyl 2-azido-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-1-thio-β-D-galactopyranoside
• CAS No.: 384346-80-9
• Molecular Formula: C₂₆H₃₅N₃O₄SSi
• Molecular Weight: 513.733

Synonyms:4-methylphenyl 2-azido-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-1-thio-β-D-galactopyranoside

Chemical Property of 4-methylphenyl 2-azido-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-1-thio-β-D-galactopyranoside

Chemical Property:

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Technology Process of 4-methylphenyl 2-azido-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-1-thio-β-D-galactopyranoside

There total 3 articles about 4-methylphenyl 2-azido-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-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: 93.0%

t-butyldimethylsiyl triflate (69739-34-0) + 4-methylphenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside (125760-23-8) → 4-methylphenyl 2-azido-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-1-thio-β-D-galactopyranoside (384346-80-9)

Guidance literature:

With pyridine; dmap; at 20 ℃; for 24h;

DOI:10.1021/ja015570t

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → 4-methylphenyl 2-azido-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-1-thio-β-D-galactopyranoside (384346-80-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / p-TsOH*H₂O / acetonitrile / 2 h / 20 °C

2: 93 percent / pyridine; DMAP / 24 h / 20 °C

With pyridine; dmap; toluene-4-sulfonic acid; In acetonitrile;

DOI:10.1021/ja015570t

Reference yield:

p-methylphenyl 2-deoxy-2-azido-1-thio-β-D-galactopyranoside (125760-22-7) → 4-methylphenyl 2-azido-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-1-thio-β-D-galactopyranoside (384346-80-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / p-TsOH*H₂O / acetonitrile / 2 h / 20 °C

2: 93 percent / pyridine; DMAP / 24 h / 20 °C

With pyridine; dmap; toluene-4-sulfonic acid; In acetonitrile;

DOI:10.1021/ja015570t

upstream raw materials:

t-butyldimethylsiyl triflate

4-methylphenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside

benzaldehyde dimethyl acetal

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

Downstream raw materials:

N^α-fluoren-9-ylmethoxycarbonyl-3-O-(2-azido-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-α-D-galactopyranosyl)-L-threonine allyl ester

N^α-fluoren-9-ylmethoxycarbonyl-3-O-[2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-threonine

N^α-fluoren-9-ylmethoxycarbonyl-3-O-(2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-L-threonine allyl ester

N^α-fluoren-9-ylmethoxycarbonyl-3-O-(2-acetamido-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-α-D-galactopyranosyl)-L-threonine

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