Acetic acid (1R,4aS,8aS)-5,5,8a-trimethyl-1-{2-[(2S,3S)-2-methyl-3-(toluene-4-sulfonyloxymethyl)-oxiranyl]-ethyl}-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-2-ylmethyl ester

Base Information

• Chemical Name: Acetic acid (1R,4aS,8aS)-5,5,8a-trimethyl-1-{2-[(2S,3S)-2-methyl-3-(toluene-4-sulfonyloxymethyl)-oxiranyl]-ethyl}-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-2-ylmethyl ester
• CAS No.: 156053-27-9
• Molecular Formula: C₂₉H₄₂O₆S
• Molecular Weight: 518.715
• Mol file: 156053-27-9.mol

Synonyms:

Chemical Property of Acetic acid (1R,4aS,8aS)-5,5,8a-trimethyl-1-{2-[(2S,3S)-2-methyl-3-(toluene-4-sulfonyloxymethyl)-oxiranyl]-ethyl}-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (1R,4aS,8aS)-5,5,8a-trimethyl-1-{2-[(2S,3S)-2-methyl-3-(toluene-4-sulfonyloxymethyl)-oxiranyl]-ethyl}-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-2-ylmethyl ester

There total 3 articles about Acetic acid (1R,4aS,8aS)-5,5,8a-trimethyl-1-{2-[(2S,3S)-2-methyl-3-(toluene-4-sulfonyloxymethyl)-oxiranyl]-ethyl}-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-2-ylmethyl ester 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:

15,17-diacetoxy-7,13E-labdadiene (78161-10-1) → Acetic acid (1R,4aS,8aS)-5,5,8a-trimethyl-1-{2-[(2S,3S)-2-methyl-3-(toluene-4-sulfonyloxymethyl)-oxiranyl]-ethyl}-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-2-ylmethyl ester (156053-27-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 264 mg / aq. K₂CO₃ / methanol / 0.5 h / Ambient temperature

2: 1.) Ti(i-PrO)4, L-(+)-diethyl tartrate, 2.) t-BuOOH / 1) CH₂Cl₂, -23 deg C, 20 min; 2) CH₂Cl₂, -20 deg C, 18 h

3: 143 mg / pyridine / 0 - 5 °C

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; potassium carbonate; In methanol;

DOI:10.1016/S0031-9422(00)90593-4

Reference yield:

p-toluenesulfonyl chloride (98-59-9) + Acetic acid (1R,4aS,8aS)-1-[2-((2S,3S)-3-hydroxymethyl-2-methyl-oxiranyl)-ethyl]-5,5,8a-trimethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-2-ylmethyl ester (156053-26-8) → Acetic acid (1R,4aS,8aS)-5,5,8a-trimethyl-1-{2-[(2S,3S)-2-methyl-3-(toluene-4-sulfonyloxymethyl)-oxiranyl]-ethyl}-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-2-ylmethyl ester (156053-27-9)

Guidance literature:

With pyridine; at 0 - 5 ℃;

DOI:10.1016/S0031-9422(00)90593-4

Reference yield:

17-acetoxy-7,13E-labdadien-15-ol (156053-25-7) → Acetic acid (1R,4aS,8aS)-5,5,8a-trimethyl-1-{2-[(2S,3S)-2-methyl-3-(toluene-4-sulfonyloxymethyl)-oxiranyl]-ethyl}-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-2-ylmethyl ester (156053-27-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Ti(i-PrO)4, L-(+)-diethyl tartrate, 2.) t-BuOOH / 1) CH₂Cl₂, -23 deg C, 20 min; 2) CH₂Cl₂, -20 deg C, 18 h

2: 143 mg / pyridine / 0 - 5 °C

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate;

DOI:10.1016/S0031-9422(00)90593-4

upstream raw materials:

p-toluenesulfonyl chloride

Acetic acid (1R,4aS,8aS)-1-[2-((2S,3S)-3-hydroxymethyl-2-methyl-oxiranyl)-ethyl]-5,5,8a-trimethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-2-ylmethyl ester

17-acetoxy-7,13E-labdadien-15-ol

15,17-diacetoxy-7,13E-labdadiene