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

Base Information

• Chemical Name: N-(4-methoxybenzyl)-1-S-(2,3,4,6-tetra-O-acetyl)-D-glucopyranosylsulfenamide
• CAS No.: 1138026-27-3
• Molecular Formula: C₂₂H₂₉NO₁₀S
• Molecular Weight: 499.539
• Mol file: 1138026-27-3.mol

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

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

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-glucopyranosylsulfenamide

There total 1 articles about N-(4-methoxybenzyl)-1-S-(2,3,4,6-tetra-O-acetyl)-D-glucopyranosylsulfenamide 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: 83.0%

4-methoxy-benzylamine (2393-23-9) + 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-glucopyranosylsulfenamide (1138026-27-3)

Guidance literature:

O²,O³,O⁴,O⁶,S-Pentaacetyl-1-thio-β-D-glucopyranose; With Diethyl 2-bromomalonate; In methanol; at 20 ℃; for 0.333333h; Inert atmosphere;

4-methoxy-benzylamine; In methanol; at 20 ℃; Inert atmosphere;

DOI:10.1021/jo9000367

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:

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-tri-O-acetyl-6-O-tert-butyldimethylsilyl)-D-glucopyranosylsulfonamide

Guidance literature:

Multi-step reaction with 4 steps

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

2: sodium methylate / methanol / 2 h / 20 °C / pH > 11

3: 1H-imidazole / N,N-dimethyl-formamide / 20 °C

4: pyridine / 3 h / 20 °C

With pyridine; 1H-imidazole; potassium permanganate; copper(ll) sulfate pentahydrate; sodium methylate; In methanol; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/acs.jmedchem.5b01228

upstream raw materials:

4-methoxy-benzylamine

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

Downstream raw materials:

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