6-epi-aucubin

Base Information

• Chemical Name: 6-epi-aucubin
• CAS No.: 82535-77-1
• Molecular Formula: C₁₅H₂₂O₉
• Molecular Weight: 346.334
• Mol file: 82535-77-1.mol

Synonyms:6-epi-aucubin

Chemical Property of 6-epi-aucubin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-epi-aucubin

There total 1 articles about 6-epi-aucubin 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:

penta-O-acetyl-6-chetoaucubin (82504-05-0) → 6-epi-aucubin (82535-77-1) + aucubin (479-98-1)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 95 ℃; for 0.166667h; Yield given. Yields of byproduct given;

DOI:10.1016/0040-4020(82)80173-7

Reference yield:

aucubin (479-98-1,82535-77-1) → Benzoic acid (2aS,3S,4S,4aR,6R,7aS,7bS)-2a,6-diethoxy-3-hydroxy-octahydro-1,7-dioxa-cyclopenta[cd]inden-4-yl ester (111563-50-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 58 percent / p-TsOH*H₂O / methanol / 264 h / Ambient temperature

2: p-TsOH*H₂O / CH₂Cl₂ / 10 h / Ambient temperature

3: OsO₄ / pyridine / 5 deg C, 5 h, then Rt, 40 h

4: pyridine; CHCl₃ / 48 h / Ambient temperature

With osmium(VIII) oxide; toluene-4-sulfonic acid; In pyridine; methanol; dichloromethane; chloroform;

DOI:10.1139/v87-311

Reference yield:

aucubin (479-98-1,82535-77-1) → C27H30O8 (111589-54-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 58 percent / p-TsOH*H₂O / methanol / 264 h / Ambient temperature

2: p-TsOH*H₂O / CH₂Cl₂ / 10 h / Ambient temperature

3: OsO₄ / pyridine / 5 deg C, 5 h, then Rt, 40 h

4: pyridine; CHCl₃ / 48 h / Ambient temperature

With osmium(VIII) oxide; toluene-4-sulfonic acid; In pyridine; methanol; dichloromethane; chloroform;

DOI:10.1139/v87-311

upstream raw materials:

penta-O-acetyl-6-chetoaucubin

Downstream raw materials:

(1R,4aR,7aS)-7-Hydroxymethyl-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-1,5-diol

aucubigenin

(5R)-2-methyl-5-(2-oxoethyl)cyclopent-1-ene-1-carbaldehyde

Benzoic acid (2aS,3S,4S,4aR,6R,7aS,7bS)-2a,6-diethoxy-3-hydroxy-octahydro-1,7-dioxa-cyclopenta[cd]inden-4-yl ester