N-(4-methoxybenzyl)-1-S-(2,3,4,6-tetra-O-acetyl)-D-glucopyranosylsulfonamide

Base Information

• Chemical Name: N-(4-methoxybenzyl)-1-S-(2,3,4,6-tetra-O-acetyl)-D-glucopyranosylsulfonamide
• CAS No.: 1138026-26-2
• Molecular Formula: C₂₂H₂₉NO₁₂S
• Molecular Weight: 531.538
• Mol file: 1138026-26-2.mol

Synonyms:N-(4-methoxybenzyl)-1-S-(2,3,4,6-tetra-O-acetyl)-D-glucopyranosylsulfonamide

Chemical Property of N-(4-methoxybenzyl)-1-S-(2,3,4,6-tetra-O-acetyl)-D-glucopyranosylsulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(4-methoxybenzyl)-1-S-(2,3,4,6-tetra-O-acetyl)-D-glucopyranosylsulfonamide

There total 3 articles about N-(4-methoxybenzyl)-1-S-(2,3,4,6-tetra-O-acetyl)-D-glucopyranosylsulfonamide 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: 40.0%

N-(4-methoxybenzyl)-1-S-(2,3,4,6-tetra-O-acetyl)-D-glucopyranosylsulfenamide (1138026-27-3) → N-(4-methoxybenzyl)-1-S-(2,3,4,6-tetra-O-acetyl)-D-glucopyranosylsulfonamide (1138026-26-2)

Guidance literature:

With potassium permanganate; copper(ll) sulfate pentahydrate; In water; acetonitrile; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.5b01228

Reference yield:

O2,O3,O4,O6,S-Pentaacetyl-1-thio-β-D-glucopyranose (6806-56-0,13639-50-4,51898-27-2,62860-10-0,63783-77-7,92217-67-9,92217-68-0,130796-15-5) → N-(4-methoxybenzyl)-1-S-(2,3,4,6-tetra-O-acetyl)-D-glucopyranosylsulfonamide (1138026-26-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Diethyl 2-bromomalonate / methanol / 0.33 h / 0.2 °C / Inert atmosphere

1.2: 20 °C / Inert atmosphere

2.1: potassium permanganate; copper(ll) sulfate pentahydrate / water; acetonitrile / 2 h / 20 °C / Inert atmosphere

With potassium permanganate; copper(ll) sulfate pentahydrate; Diethyl 2-bromomalonate; In methanol; water; acetonitrile;

DOI:10.1021/acs.jmedchem.5b01228

Reference yield:

4-methoxy-benzylamine (2393-23-9) → N-(4-methoxybenzyl)-1-S-(2,3,4,6-tetra-O-acetyl)-D-glucopyranosylsulfonamide (1138026-26-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Diethyl 2-bromomalonate / methanol / 0.33 h / 0.2 °C / Inert atmosphere

1.2: 20 °C / Inert atmosphere

2.1: potassium permanganate; copper(ll) sulfate pentahydrate / water; acetonitrile / 2 h / 20 °C / Inert atmosphere

With potassium permanganate; copper(ll) sulfate pentahydrate; Diethyl 2-bromomalonate; In methanol; water; acetonitrile;

DOI:10.1021/acs.jmedchem.5b01228

upstream raw materials:

N-(4-methoxybenzyl)-1-S-(2,3,4,6-tetra-O-acetyl)-D-glucopyranosylsulfenamide

O²,O³,O⁴,O⁶,S-Pentaacetyl-1-thio-β-D-glucopyranose

4-methoxy-benzylamine