(S)-[3,4-dihydro-6-benzyloxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl]methyl trifluoromethane-sulfonate

Base Information

• Chemical Name: (S)-[3,4-dihydro-6-benzyloxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl]methyl trifluoromethane-sulfonate
• CAS No.: 906079-28-5
• Molecular Formula: C₂₂H₂₅F₃O₅S
• Molecular Weight: 458.499
• Mol file: 906079-28-5.mol

Synonyms:(S)-[3,4-dihydro-6-benzyloxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl]methyl trifluoromethane-sulfonate

Chemical Property of (S)-[3,4-dihydro-6-benzyloxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl]methyl trifluoromethane-sulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-[3,4-dihydro-6-benzyloxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl]methyl trifluoromethane-sulfonate

There total 25 articles about (S)-[3,4-dihydro-6-benzyloxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl]methyl trifluoromethane-sulfonate 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: 92.0%

trifluoromethylsulfonic anhydride (358-23-6) + (S)-(-)-6-benzyloxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-ylmethanol (69371-87-5) → (S)-[3,4-dihydro-6-benzyloxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl]methyl trifluoromethane-sulfonate (906079-28-5)

Guidance literature:

With pyridine; triethylamine; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1021/jacs.8b02607

Reference yield:

(S)-(+)-6-hydroxy-2,5,7,8-tetramethylchroman-2-methanol (69427-83-4) → (S)-[3,4-dihydro-6-benzyloxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl]methyl trifluoromethane-sulfonate (906079-28-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / sodium hydride / tetrahydrofuran / 20 h / 20 °C

2: 62 percent / triethylamine / CH₂Cl₂ / 0.5 h / -10 °C

With sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.bmc.2006.03.035

Reference yield:

[6-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5,7,8-trimethyl-chroman-2-yl]-methanol (906079-25-2) → (S)-[3,4-dihydro-6-benzyloxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl]methyl trifluoromethane-sulfonate (906079-28-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 86 percent / triethylamine; 4-dimethyaminopyridine / CH₂Cl₂ / 288 h / 20 °C

2: 36 percent / lithium triethylborohydride / tetrahydrofuran / 16 h

3: 100 percent / glacial acetic acid; N-tetrabutylammonium fluoride / tetrahydrofuran / 72 h / 20 °C

4: 80 percent / sodium hydride / tetrahydrofuran / 20 h / 20 °C

5: 62 percent / triethylamine / CH₂Cl₂ / 0.5 h / -10 °C

With dmap; tetrabutyl ammonium fluoride; sodium hydride; lithium triethylborohydride; acetic acid; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.bmc.2006.03.035

upstream raw materials:

trifluoromethylsulfonic anhydride

(S)-(-)-6-benzyloxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-ylmethanol

6-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-2,5,7,8-tetramethyl-chroman

[6-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5,7,8-trimethyl-chroman-2-yl]-methanol

Downstream raw materials:

(2S)-6-(benzyloxy)-2,5,7,8-tetramethyl-2-((3E,7E)-4,8,12-trimethyl-2-(phenylsulfonyl)trideca-3,7,11-trien-1-yl)chromane

(R)-6-(benzyloxy)-2,5,7,8-tetramethyl-2-((3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl)chromane

alpha-tocotrienol

(2R,4’R,8’S)-α-tocopherol