prop-2-en-1-yl 2-(acetylamino)-4,6-O-benzylidene-2-deoxy-3-O-(2,3-di-O-benzoyl-6-methyl-β-D-glucopyranosyl)-α-D-glucopyranoside

Base Information

• Chemical Name: prop-2-en-1-yl 2-(acetylamino)-4,6-O-benzylidene-2-deoxy-3-O-(2,3-di-O-benzoyl-6-methyl-β-D-glucopyranosyl)-α-D-glucopyranoside
• CAS No.: 1419710-81-8
• Molecular Formula: C₃₉H₄₁NO₁₄
• Molecular Weight: 747.753

Synonyms:prop-2-en-1-yl 2-(acetylamino)-4,6-O-benzylidene-2-deoxy-3-O-(2,3-di-O-benzoyl-6-methyl-β-D-glucopyranosyl)-α-D-glucopyranoside

Chemical Property of prop-2-en-1-yl 2-(acetylamino)-4,6-O-benzylidene-2-deoxy-3-O-(2,3-di-O-benzoyl-6-methyl-β-D-glucopyranosyl)-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of prop-2-en-1-yl 2-(acetylamino)-4,6-O-benzylidene-2-deoxy-3-O-(2,3-di-O-benzoyl-6-methyl-β-D-glucopyranosyl)-α-D-glucopyranoside

There total 7 articles about prop-2-en-1-yl 2-(acetylamino)-4,6-O-benzylidene-2-deoxy-3-O-(2,3-di-O-benzoyl-6-methyl-β-D-glucopyranosyl)-α-D-glucopyranoside 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: 35.0%

prop-2-en-1-yl 2-(acetylamino)-4,6-O-benzylidene-2-deoxy-3-O-{2,3-di-O-benzoyl-4-O-[tert-butyl(dimethyl)silyl]-6-methyl-β-D-glucopyranosyl}-α-D-glucopyranoside (1419711-25-3) → prop-2-en-1-yl 2-(acetylamino)-4,6-O-benzylidene-2-deoxy-3-O-(2,3-di-O-benzoyl-6-methyl-β-D-glucopyranosyl)-α-D-glucopyranoside (1419710-81-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1016/j.bmc.2012.11.025

Reference yield:

C41H48O8SSi → prop-2-en-1-yl 2-(acetylamino)-4,6-O-benzylidene-2-deoxy-3-O-(2,3-di-O-benzoyl-6-methyl-β-D-glucopyranosyl)-α-D-glucopyranoside (1419710-81-8)

Guidance literature:

Multi-step reaction with 5 steps

1: N-iodo-succinimide; silver trifluoromethanesulfonate / dichloromethane / 1 h / 0 - 20 °C / Molecular sieve; Inert atmosphere

2: sodium hydrogencarbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone / water; dichloromethane / 5 h / 20 °C / Inert atmosphere

3: [bis(acetoxy)iodo]benzene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / water; dichloromethane / 7 h / 20 °C / Inert atmosphere

4: potassium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

5: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C

With N-iodo-succinimide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; tetrabutyl ammonium fluoride; silver trifluoromethanesulfonate; sodium hydrogencarbonate; potassium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2012.11.025

Reference yield:

prop-2-en-1-yl 2-(acetylamino)-4,6-O-benzylidene-2-deoxy-3-O-{2,3-di-O-benzoyl-4-O-[tert-butyl(dimethyl)silyl]-6-O-(4-methoxybenzyl)-β-D-glucopyranosyl}-α-D-glucopyranoside (1419711-15-1) → prop-2-en-1-yl 2-(acetylamino)-4,6-O-benzylidene-2-deoxy-3-O-(2,3-di-O-benzoyl-6-methyl-β-D-glucopyranosyl)-α-D-glucopyranoside (1419710-81-8)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium hydrogencarbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone / water; dichloromethane / 5 h / 20 °C / Inert atmosphere

2: [bis(acetoxy)iodo]benzene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / water; dichloromethane / 7 h / 20 °C / Inert atmosphere

3: potassium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

4: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; potassium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2012.11.025

upstream raw materials:

prop-2-en-1-yl 2-(acetylamino)-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside

methyl 2,3-di-O-benzoyl-4-O-[tert-butyl(dimethyl)silyl]-1-O-(2,2,2-trichloroethanimidoyl)-α-D-glucopyranuronate

prop-2-en-1-yl 2-(acetylamino)-4,6-O-benzylidene-2-deoxy-3-O-{2,3-di-O-benzoyl-4-O-[tert-butyl(dimethyl)silyl]-6-O-(4-methoxybenzyl)-β-D-glucopyranosyl}-α-D-glucopyranoside

prop-2-en-1-yl 2-(acetylamino)-4,6-O-benzylidene-2-deoxy-3-O-{2,3-di-O-benzoyl-4-O-[tert-butyl(dimethyl)silyl]-β-D-glucopyranosyl}-α-D-glucopyranoside

Downstream raw materials:

prop-2-en-1-yl 2,3-di-O-benzoyl-4-O-[tertbutyl(dimethyl)silyl]-6-methyl-β-D-glucopyranuronosyl-(1→3)-4,6-O-benzylidene-2-deoxy-2-{[(2,2,2-trichloroethoxy)carbonyl]-amino}-β-D-glucopyranosyl-(1→4)-2,3-di-O-benzoyl-6-methyl-β-D-glucopyranuronosyl-(1→3)-2-(acetylamino)-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside

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