Tatariid A

Base Information

• Chemical Name: Tatariid A
• CAS No.: 1229005-35-9
• Molecular Formula: C12H16O5
• Molecular Weight: 240.256
• Mol file: 1229005-35-9.mol

Synonyms:Tatariid A;Tatarinoid A

Chemical Property of Tatariid A

Chemical Property:

• Boiling Point: 384.1±37.0 °C(Predicted)
• PKA: 13.02±0.20(Predicted)
• PSA: 64.99000
• Density: 1.158±0.06 g/cm3(Predicted)
• LogP: 1.27590

Purity/Quality:

98%min ^*data from raw suppliers

TatarinoidA ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Tatariid A

There total 6 articles about Tatariid A 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: 78.0%

(R)-2-(tert-butyldimethylsilyloxy)-1-(2,4,5-trimethoxyphenyl)propan-1-one (1422453-73-3) → (2R)-1-(2,4,5-trimethoxyphenyl)propan-2-ol-1-one (1229005-35-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 2h; Inert atmosphere;

DOI:10.1016/j.tetlet.2012.10.104

Reference yield:

1-(2,4,5-Trimethoxyphenyl)propan-1-ol (29652-82-2) → (2R)-1-(2,4,5-trimethoxyphenyl)propan-2-ol-1-one (1229005-35-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: manganese(IV) oxide / dichloromethane / 24 h / Reflux

2.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 0.75 h

2.2: 20 °C

3.1: (-)-N-[(4S,5S)-2,2-dimethyl-4-phenyl-1,3-dioxan-5-yl]-5H-dibenzo[c,e]azepinium tetraphenylborate; tetraphenylphosphonium monoperoxysulfate / dichloromethane; chloroform; acetonitrile / 48 h / -30 °C

4.1: camphor-10-sulfonic acid / methanol

With manganese(IV) oxide; n-butyllithium; camphor-10-sulfonic acid; tetraphenylphosphonium monoperoxysulfate; diisopropylamine; (-)-N-[(4S,5S)-2,2-dimethyl-4-phenyl-1,3-dioxan-5-yl]-5H-dibenzo[c,e]azepinium tetraphenylborate; In tetrahydrofuran; methanol; hexane; dichloromethane; chloroform; acetonitrile;

DOI:10.1021/acs.joc.8b02354

Reference yield:

isoacoramone (3904-18-5) → (2R)-1-(2,4,5-trimethoxyphenyl)propan-2-ol-1-one (1229005-35-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 0.75 h

1.2: 20 °C

2.1: (-)-N-[(4S,5S)-2,2-dimethyl-4-phenyl-1,3-dioxan-5-yl]-5H-dibenzo[c,e]azepinium tetraphenylborate; tetraphenylphosphonium monoperoxysulfate / dichloromethane; chloroform; acetonitrile / 48 h / -30 °C

3.1: camphor-10-sulfonic acid / methanol

With n-butyllithium; camphor-10-sulfonic acid; tetraphenylphosphonium monoperoxysulfate; diisopropylamine; (-)-N-[(4S,5S)-2,2-dimethyl-4-phenyl-1,3-dioxan-5-yl]-5H-dibenzo[c,e]azepinium tetraphenylborate; In tetrahydrofuran; methanol; hexane; dichloromethane; chloroform; acetonitrile;

DOI:10.1021/acs.joc.8b02354

upstream raw materials:

(R)-2-(tert-butyldimethylsilyloxy)-1-(2,4,5-trimethoxyphenyl)propan-1-one

1-(2,4,5-Trimethoxyphenyl)propan-1-ol

isoacoramone

2-(2,4,5-trimethoxyphenyl)acetaldehyde

Refernces

• 1、 Slutskyy, Yuriy,Jewell, William T.,Lucero, Claudia G.. "Syntheses of (-)-Tatarinoid A, (±)-Tatarinoid B, and (-)-Tatarinoid C". supporting information. p. 210 - 212. Retrieved 2013/02/22.