ethyl 3-O-allyl-6-O-levulinoyl-2,4-di-O-toluoyl-1-thio-α-D-glucopyranoside

Base Information

• Chemical Name: ethyl 3-O-allyl-6-O-levulinoyl-2,4-di-O-toluoyl-1-thio-α-D-glucopyranoside
• CAS No.: 182871-18-7
• Molecular Formula: C₃₂H₃₈O₉S
• Molecular Weight: 598.714

Synonyms:ethyl 3-O-allyl-6-O-levulinoyl-2,4-di-O-toluoyl-1-thio-α-D-glucopyranoside

Chemical Property of ethyl 3-O-allyl-6-O-levulinoyl-2,4-di-O-toluoyl-1-thio-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

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Technology Process of ethyl 3-O-allyl-6-O-levulinoyl-2,4-di-O-toluoyl-1-thio-α-D-glucopyranoside

There total 3 articles about ethyl 3-O-allyl-6-O-levulinoyl-2,4-di-O-toluoyl-1-thio-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:

levulinic acid (123-76-2) → ethyl 3-O-allyl-6-O-levulinoyl-2,4-di-O-toluoyl-1-thio-α-D-glucopyranoside (182871-18-7)

Guidance literature:

Multi-step reaction with 2 steps

1: DABCO, CMPI / tetrahydrofuran / 1.5 h / 0 °C

2: DMAP / pyridine; 1,2-dichloro-ethane / Ambient temperature

With 1,4-diaza-bicyclo[2.2.2]octane; dmap; In tetrahydrofuran; pyridine; 1,2-dichloro-ethane;

DOI:10.1271/bbb.60.1308

Reference yield:

ethyl 3-O-allyl-1-thio-α-D-glucopyranoside → ethyl 3-O-allyl-6-O-levulinoyl-2,4-di-O-toluoyl-1-thio-α-D-glucopyranoside (182871-18-7)

Guidance literature:

Multi-step reaction with 2 steps

1: DABCO, CMPI / tetrahydrofuran / 1.5 h / 0 °C

2: DMAP / pyridine; 1,2-dichloro-ethane / Ambient temperature

With 1,4-diaza-bicyclo[2.2.2]octane; dmap; In tetrahydrofuran; pyridine; 1,2-dichloro-ethane;

DOI:10.1271/bbb.60.1308

Reference yield:

4-methyl-benzoyl chloride (874-60-2) + 4-Oxo-pentanoic acid (2R,3R,4S,5R,6R)-4-allyloxy-6-ethylsulfanyl-3,5-dihydroxy-tetrahydro-pyran-2-ylmethyl ester (182872-25-9) → ethyl 3-O-allyl-6-O-levulinoyl-2,4-di-O-toluoyl-1-thio-α-D-glucopyranoside (182871-18-7)

Guidance literature:

With dmap; In pyridine; 1,2-dichloro-ethane; Yield given; Ambient temperature;

DOI:10.1271/bbb.60.1308

upstream raw materials:

4-methyl-benzoyl chloride

4-Oxo-pentanoic acid (2R,3R,4S,5R,6R)-4-allyloxy-6-ethylsulfanyl-3,5-dihydroxy-tetrahydro-pyran-2-ylmethyl ester

levulinic acid

Downstream raw materials:

2-(trimethylsilyl)ethyl O-(3-O-allyl-6-O-levulinoyl-2,4-di-O-toluoyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-toluoyl-β-D-glucopyranoside

O-[(3-O-allyl-6-O-levulinoyl-2,4-di-O-toluoyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-toluoyl-α-D-glucopyranosyl)]trichloroacetamidate

2-(trimethylsilyl)ethyl O-(3-O-allyl-2,4-di-O-toluoyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-toluoyl-β-D-glucopyranoside

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