4-methylphenyl 5-azido-5,6-dideoxy-2,3-O-1-methylethylidene-1-thio-α-L-talofuranoside

Base Information

• Chemical Name: 4-methylphenyl 5-azido-5,6-dideoxy-2,3-O-1-methylethylidene-1-thio-α-L-talofuranoside
• CAS No.: 1356827-01-4
• Molecular Formula: C₁₆H₂₁N₃O₃S
• Molecular Weight: 335.427
• Mol file: 1356827-01-4.mol

Synonyms:4-methylphenyl 5-azido-5,6-dideoxy-2,3-O-1-methylethylidene-1-thio-α-L-talofuranoside

Chemical Property of 4-methylphenyl 5-azido-5,6-dideoxy-2,3-O-1-methylethylidene-1-thio-α-L-talofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-methylphenyl 5-azido-5,6-dideoxy-2,3-O-1-methylethylidene-1-thio-α-L-talofuranoside

There total 5 articles about 4-methylphenyl 5-azido-5,6-dideoxy-2,3-O-1-methylethylidene-1-thio-α-L-talofuranoside 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: 55.0%

4-methylphenyl 6-deoxy-5-O-tosyl-2,3-O-1-methylethylidene-1-thio-β-D-allofuranoside (1356826-97-5) → 4-methylphenyl 5-azido-5,6-dideoxy-2,3-O-1-methylethylidene-1-thio-α-L-talofuranoside (1356827-01-4)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium azide; In N,N-dimethyl-formamide; at 20 - 70 ℃;

Reference yield:

4-methylphenyl 6-deoxy-2,3-O-1-methylethylidene-1-thio-β-Dallofuranoside (1356826-95-3) → 4-methylphenyl 5-azido-5,6-dideoxy-2,3-O-1-methylethylidene-1-thio-α-L-talofuranoside (1356827-01-4)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / dmap / 0 - 20 °C

2: N,N,N,N,N,N-hexamethylphosphoric triamide; sodium azide / N,N-dimethyl-formamide / 20 - 70 °C

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium azide; dmap; In N,N-dimethyl-formamide;

Reference yield:

p-tolyl 1-thio-β-D-ribofuranoside (1131610-84-8) → 4-methylphenyl 5-azido-5,6-dideoxy-2,3-O-1-methylethylidene-1-thio-α-L-talofuranoside (1356827-01-4)

Guidance literature:

Multi-step reaction with 5 steps

1: magnesium sulfate / (1S)-10-camphorsulfonic acid / acetone / 5 h / 20 °C

2: magnesium sulfate; Dess-Martin periodane / dichloromethane / 8 h / 20 °C

3: tetrahydrofuran / 2.5 h / -30 °C

4: pyridine / dmap / 0 - 20 °C

5: N,N,N,N,N,N-hexamethylphosphoric triamide; sodium azide / N,N-dimethyl-formamide / 20 - 70 °C

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium azide; magnesium sulfate; Dess-Martin periodane; dmap; (1S)-10-camphorsulfonic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone;

upstream raw materials:

4-methylphenyl 6-deoxy-2,3-O-1-methylethylidene-1-thio-β-Dallofuranoside

4-methylphenyl 6-deoxy-5-O-tosyl-2,3-O-1-methylethylidene-1-thio-β-D-allofuranoside

p-tolyl 1-thio-β-D-ribofuranoside

4-methylphenyl 2,3-O-1-methylethylidene-1-thio-β-D-ribopentodialdo-1,4-furanoside

Downstream raw materials:

C₁₃H₁₇N₃O₃S

ELX-05

ELX-01

6′-(R)-methyl-5-O-(5-amino-5,6-dideoxy-α-L-talofuranosyl)-paromamine