3,5,6-trideoxy-3-(2-bromobenzyl-para-toluenesulfonylamino)-1,2-O-isopropylidene-α-D-xylo-hexenofuranoside

Base Information

• Chemical Name: 3,5,6-trideoxy-3-(2-bromobenzyl-para-toluenesulfonylamino)-1,2-O-isopropylidene-α-D-xylo-hexenofuranoside
• CAS No.: 869064-86-8
• Molecular Formula: C₂₃H₂₆BrNO₅S
• Molecular Weight: 508.433

Synonyms:3,5,6-trideoxy-3-(2-bromobenzyl-para-toluenesulfonylamino)-1,2-O-isopropylidene-α-D-xylo-hexenofuranoside

Chemical Property of 3,5,6-trideoxy-3-(2-bromobenzyl-para-toluenesulfonylamino)-1,2-O-isopropylidene-α-D-xylo-hexenofuranoside

Chemical Property:

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Technology Process of 3,5,6-trideoxy-3-(2-bromobenzyl-para-toluenesulfonylamino)-1,2-O-isopropylidene-α-D-xylo-hexenofuranoside

There total 8 articles about 3,5,6-trideoxy-3-(2-bromobenzyl-para-toluenesulfonylamino)-1,2-O-isopropylidene-α-D-xylo-hexenofuranoside 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: 67.0%

N-(2,2-dimethyl-5-vinyl-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl)-4-methyl benzenesulphonamide + 1-Bromo-2-bromomethyl-benzene (3433-80-5) → 3,5,6-trideoxy-3-(2-bromobenzyl-para-toluenesulfonylamino)-1,2-O-isopropylidene-α-D-xylo-hexenofuranoside (869064-86-8)

Guidance literature:

N-(2,2-dimethyl-5-vinyl-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl)-4-methyl benzenesulphonamide; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 0.333333h;

1-Bromo-2-bromomethyl-benzene; With tetra-(n-butyl)ammonium iodide; In N,N-dimethyl-formamide; mineral oil; at 20 ℃; for 8h;

DOI:10.1039/c3ra45363d

Reference yield:

N-(2-bromo-benzyl)-N-[5-(1,2-dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-4-methyl-benzenesulfonamide → 3,5,6-trideoxy-3-(2-bromobenzyl-para-toluenesulfonylamino)-1,2-O-isopropylidene-α-D-xylo-hexenofuranoside (869064-86-8)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In toluene; for 4h; Heating;

DOI:10.1055/s-2005-870012

Reference yield:

3-deoxy-3-(2-bromobenzyl-para-toluenesulfonylamino)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranoside (869064-84-6) → 3,5,6-trideoxy-3-(2-bromobenzyl-para-toluenesulfonylamino)-1,2-O-isopropylidene-α-D-xylo-hexenofuranoside (869064-86-8)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. AcOH / 12 h / 20 °C

2: imidazole; Ph₃P; I₂ / toluene / 4 h / Heating

With 1H-imidazole; iodine; acetic acid; triphenylphosphine; In toluene;

DOI:10.1055/s-2005-870012

upstream raw materials:

3-deoxy-3-(2-bromobenzyl-para-toluenesulfonylamino)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranoside

p-toluenesulfonyl chloride

3-amino-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

N-[(3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-4-methyl-benzenesulfonamide

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