3,4-di-O-acetyl-1,2-O-<1-(exo-p-tolylthio)ethylidene>-β-L-rhamnopyranose

Base Information

• Chemical Name: 3,4-di-O-acetyl-1,2-O-<1-(exo-p-tolylthio)ethylidene>-β-L-rhamnopyranose
• CAS No.: 75556-26-2
• Molecular Formula: C₁₉H₂₄O₇S
• Molecular Weight: 396.461

Synonyms:3,4-di-O-acetyl-1,2-O-<1-(exo-p-tolylthio)ethylidene>-β-L-rhamnopyranose

Chemical Property of 3,4-di-O-acetyl-1,2-O-<1-(exo-p-tolylthio)ethylidene>-β-L-rhamnopyranose

Chemical Property:

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Technology Process of 3,4-di-O-acetyl-1,2-O-<1-(exo-p-tolylthio)ethylidene>-β-L-rhamnopyranose

There total 2 articles about 3,4-di-O-acetyl-1,2-O-<1-(exo-p-tolylthio)ethylidene>-β-L-rhamnopyranose 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: 46.0%

2,3,4-tri-O-acetyl-6-deoxy-beta-L-mannopyranosyl bromide (39524-38-4) + para-thiocresol (106-45-6) → 3,4-di-O-acetyl-1,2-O-<1-(exo-p-tolylthio)ethylidene>-β-L-rhamnopyranose (75556-26-2) + 3,4-di-O-acetyl-1,2-O-(1-(endo-p-tolylthio)ethylidene)-beta-L-rhamnopyranose (80877-04-9)

Guidance literature:

With 2,4,6-trimethyl-pyridine; In nitromethane; at 20 ℃; for 48h;

DOI:10.1007/BF00950593

Reference yield:

2,3,4-tri-O-acetyl-6-deoxy-beta-L-mannopyranosyl bromide (39524-38-4) + para-thiocresol (106-45-6) → 2,3,4-Tri-O-acetyl-1,5-anhydro-6-deoxy-L-arabino-hex-1-enitol (75556-27-3) + 3,4-di-O-acetyl-1,2-O-<1-(exo-p-tolylthio)ethylidene>-β-L-rhamnopyranose (75556-26-2) + 3,4-di-O-acetyl-1,2-O-(1-(endo-p-tolylthio)ethylidene)-beta-L-rhamnopyranose (80877-04-9) + p-methylphenyl 2,3,4-tri-O-acetyl-1-thio-L-rhamnopyranoside

Guidance literature:

With 2,4,6-trimethyl-pyridine; In nitromethane; Yields of byproduct given; 1.) 40-50 deg C, 5 h, 2.) 20 deg C, 3.) 50 deg C, 5 h;

DOI:10.1007/BF00950593

Reference yield:

3,4-di-O-acetyl-1,2-O-<1-(exo-p-tolylthio)ethylidene>-β-L-rhamnopyranose (75556-26-2) → (2S,3aR,5S,6R,7R,7aR)-2,5-Dimethyl-2-p-tolylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol (101144-05-2)

Guidance literature:

With sodium methylate; In pyridine; methanol; for 0.0833333h;

DOI:10.1007/BF01142797

upstream raw materials:

2,3,4-tri-O-acetyl-6-deoxy-beta-L-mannopyranosyl bromide

para-thiocresol

Downstream raw materials:

(2S,3aR,5S,6R,7R,7aR)-2,5-Dimethyl-2-p-tolylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol

3-O-(2-O-acetyl-3,4-di-O-benzoyl-α-L-rhamnopyranosyl)-4-O-benzoyl-1,2-O-<1-(exo-cyano)ethylidene>-β-L-rhamnopyranose

3,4-di-O-benzoyl-1,2-O-<1-(exo-p-tolylthio)ethylidene>-β-L-rhamnopyranose

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