methyl 5-O-benzyl-2,3-dideoxy-3-C-(p)-tolylsulfonyl-β-D-erythro-pent-2-enofuranoside

Base Information

• Chemical Name: methyl 5-O-benzyl-2,3-dideoxy-3-C-(p)-tolylsulfonyl-β-D-erythro-pent-2-enofuranoside
• CAS No.: 476645-50-8
• Molecular Formula: C₂₀H₂₂O₅S
• Molecular Weight: 374.458
• Mol file: 476645-50-8.mol

Synonyms:methyl 5-O-benzyl-2,3-dideoxy-3-C-(p)-tolylsulfonyl-β-D-erythro-pent-2-enofuranoside

Chemical Property of methyl 5-O-benzyl-2,3-dideoxy-3-C-(p)-tolylsulfonyl-β-D-erythro-pent-2-enofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 5-O-benzyl-2,3-dideoxy-3-C-(p)-tolylsulfonyl-β-D-erythro-pent-2-enofuranoside

There total 12 articles about methyl 5-O-benzyl-2,3-dideoxy-3-C-(p)-tolylsulfonyl-β-D-erythro-pent-2-enofuranoside 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: 92.0%

methyl 5-O-benzyl-3-deoxy-3-C-p-tolylsulfonyl-β-D-ribofuranoside (476645-48-4) → methyl 5-O-benzyl-2,3-dideoxy-3-C-(p)-tolylsulfonyl-β-D-erythro-pent-2-enofuranoside (476645-50-8)

Guidance literature:

With pyridine; methanesulfonyl chloride; at 0 - 20 ℃; for 24h;

DOI:10.1055/s-2002-32960

Reference yield: 87.0%

methyl 5-O-benzyl-3-deoxy-3-C-p-tolylsulfonyl-β-D-xylofuranoside (611182-23-1) → methyl 5-O-benzyl-2,3-dideoxy-3-C-(p)-tolylsulfonyl-β-D-erythro-pent-2-enofuranoside (476645-50-8)

Guidance literature:

With pyridine; methanesulfonyl chloride; at 4 ℃; for 24h;

DOI:10.1016/S0040-4020(03)01059-7

Reference yield:

5-O-benzyl-1,2-O-isopropylidene-3-O-tosyl-α-D-xylofuranose → methyl 5-O-benzyl-2,3-dideoxy-3-C-(p)-tolylsulfonyl-β-D-erythro-pent-2-enofuranoside (476645-50-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 59 percent / NaOMe / dimethylformamide / 4 h / 120 °C

2: 55 percent / H₂SO₄ / 3.5 h / Heating

3: 93 percent / magnesium monoperoxyphthalate / methanol / 3 h / 20 °C

4: 92 percent / MsCl; pyridine / 24 h / 4 °C

With pyridine; sulfuric acid; sodium methylate; magnesium monoperoxyphthalate hexahydrate; methanesulfonyl chloride; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(03)01059-7

upstream raw materials:

methyl 5-O-benzyl-3-deoxy-3-C-p-tolylsulfonyl-β-D-ribofuranoside

methyl 5-O-benzyl-3-deoxy-3-C-p-tolylsulfonyl-β-D-xylofuranoside

5-O-benzyl-3-oxo-1,2-O-isopropylidene-α-D-xylofuranose

Toluene-4-sulfonic acid (2R,3R,4R,5R)-2-benzyloxymethyl-4-hydroxy-5-methoxy-tetrahydro-furan-3-yl ester

Downstream raw materials:

methyl 5-O-benzyl-2,3-dideoxy-2-pyrrolidino-3-C-(p-tolylsulfonyl)-β-D-arabinofuranoside

methyl 5-O-benzyl-2-cyclohexylamino-2,3-dideoxy-3-C-(p-tolylsulfonyl)-β-D-arabinofuranoside

methyl 5-O-benzyl-2-benzylamino-2,3-dideoxy-3-C-(p-tolylsulfonyl)-β-D-arabinofuranoside

methyl 2-amino-5-O-benzyl-2,3-dideoxy-3-C-(p-tolylsulfonyl)-β-D-arabinofuranoside