(+)-tarchonanthuslactone

Base Information

• Chemical Name: (+)-tarchonanthuslactone
• CAS No.: 123537-99-5
• Molecular Formula: C₁₇H₂₀O₆
• Molecular Weight: 320.342
• Mol file: 123537-99-5.mol

Synonyms:(+)-tarchonanthuslactone

Chemical Property of (+)-tarchonanthuslactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-tarchonanthuslactone

There total 15 articles about (+)-tarchonanthuslactone 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: 88.0%

(S)-1-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)propan-2-yl 3-(3,4-bis((tert-butyldimethylsilyl)oxy) phenyl)propanoate → (+)-tarchonanthuslactone (123537-99-5)

Guidance literature:

With tetrabutyl ammonium fluoride; benzoic acid; at 20 ℃; for 1h;

DOI:10.1055/s-0034-1378784

Reference yield:

((2S,6S)-2-Methoxy-6-methyl-4-oxo-tetrahydro-pyran-2-yl)-acetic acid tert-butyl ester (88559-60-8,96479-68-4,116561-88-7) → 3-(3,4-Dihydroxy-phenyl)-propionic acid (R)-1-methyl-2-((S)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-ethyl ester (71939-67-8,116561-89-8,116561-91-2,123537-99-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 17 percent / n-Bu₄NBH₄ / tetrahydrofuran; H₂O

2: 1.) HCl, 2.) NaBH₄ / 1.) THF, 2.) MeOH

3: 41 percent / CSA / benzene

4: 35 percent / (EtO)2POCl, Et₃N, DMAP / acetonitrile

5: n-Bu₄NF / tetrahydrofuran

With hydrogenchloride; dmap; sodium tetrahydroborate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; tetrabutylammonium borohydride; diethyl chlorophosphate; triethylamine; In tetrahydrofuran; water; acetonitrile; benzene;

DOI:10.1016/S0040-4039(00)96807-2

Reference yield:

3,4-bis(O-tert-butyldimethylsilyl)-3,4-dihydroxyhydrocinnamic acid (116511-71-8) → 3-(3,4-Dihydroxy-phenyl)-propionic acid (R)-1-methyl-2-((S)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-ethyl ester (71939-67-8,116561-89-8,116561-91-2,123537-99-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 35 percent / (EtO)2POCl, Et₃N, DMAP / acetonitrile

2: n-Bu₄NF / tetrahydrofuran

With dmap; tetrabutyl ammonium fluoride; diethyl chlorophosphate; triethylamine; In tetrahydrofuran; acetonitrile;

DOI:10.1016/S0040-4039(00)96807-2

upstream raw materials:

((2S,4S,6S)-4-Hydroxy-2-methoxy-6-methyl-tetrahydro-pyran-2-yl)-acetic acid tert-butyl ester

((2S,6S)-2-Methoxy-6-methyl-4-oxo-tetrahydro-pyran-2-yl)-acetic acid tert-butyl ester

3-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid (S)-2-((S)-2-{3-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionyloxy}-propyl)-6-oxo-tetrahydro-pyran-4-yl ester

3-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid (R)-1-methyl-2-((S)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-ethyl ester