Methyl 3-O-methyl-4-O-p-toluenesulfonyl-2-deoxy-β-D-erythro-pentopyranoside

Base Information

• Chemical Name: Methyl 3-O-methyl-4-O-p-toluenesulfonyl-2-deoxy-β-D-erythro-pentopyranoside
• CAS No.: 147860-14-8
• Molecular Formula: C₁₄H₂₀O₆S
• Molecular Weight: 316.375
• Mol file: 147860-14-8.mol

Synonyms:Methyl 3-O-methyl-4-O-p-toluenesulfonyl-2-deoxy-β-D-erythro-pentopyranoside

Chemical Property of Methyl 3-O-methyl-4-O-p-toluenesulfonyl-2-deoxy-β-D-erythro-pentopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl 3-O-methyl-4-O-p-toluenesulfonyl-2-deoxy-β-D-erythro-pentopyranoside

There total 9 articles about Methyl 3-O-methyl-4-O-p-toluenesulfonyl-2-deoxy-β-D-erythro-pentopyranoside 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: 96.0%

Methyl 4-O-p-toluenesulfonyl-2-deoxy-β-D-erythro-pentopyranoside (147860-16-0) + methyl iodide (74-88-4) → Methyl 3-O-methyl-4-O-p-toluenesulfonyl-2-deoxy-β-D-erythro-pentopyranoside (147860-14-8)

Guidance literature:

With silver(l) oxide; In N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1016/0040-4039(93)85082-8

Reference yield: 91.0%

Methyl 3-O-methyl-2-deoxy-β-D-erythro-pentopyranoside (147923-02-2) + p-toluenesulfonyl chloride (98-59-9) → Methyl 3-O-methyl-4-O-p-toluenesulfonyl-2-deoxy-β-D-erythro-pentopyranoside (147860-14-8)

Guidance literature:

With pyridine;

DOI:10.1016/0040-4039(93)85082-8

Reference yield:

methyl 2-deoxy-β-D-erythro-pentopyranoside (17676-20-9) → Methyl 3-O-methyl-4-O-p-toluenesulfonyl-2-deoxy-β-D-erythro-pentopyranoside (147860-14-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) Bu₂SnO, 2.) Bu₄NBr / 1.) toluene, reflux, 12 h, 2.) reflux, 48 h

2: 95 percent / pyridine / 1.) o-5 deg C, 0.5 h, 2.) -5 deg C, 72 h

3: 84 percent / H₂ / 10percent Pd/C / 760 Torr / 1.) ethyl acetate, 16 h, 2.) EtOH, 17 h

4: 96 percent / Ag₂O / dimethylformamide / 27 h / Ambient temperature

With pyridine; tetrabutylammomium bromide; hydrogen; di(n-butyl)tin oxide; silver(l) oxide; palladium on activated charcoal; In N,N-dimethyl-formamide;

upstream raw materials:

Methyl 3-O-methyl-2-deoxy-β-D-erythro-pentopyranoside

p-toluenesulfonyl chloride

Methyl 4-O-p-toluenesulfonyl-2-deoxy-β-D-erythro-pentopyranoside

methyl iodide

Downstream raw materials:

((3S,4S,6R)-4,6-Dimethoxy-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester