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

Base Information

• Chemical Name: (S)-(+)-2-acetoxymethyl-6-benzyloxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran
• CAS No.: 262849-34-3
• Molecular Formula: C₂₃H₂₈O₄
• Molecular Weight: 368.473
• Mol file: 262849-34-3.mol

Synonyms:(S)-(+)-2-acetoxymethyl-6-benzyloxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran

Chemical Property of (S)-(+)-2-acetoxymethyl-6-benzyloxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-(+)-2-acetoxymethyl-6-benzyloxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran

There total 16 articles about (S)-(+)-2-acetoxymethyl-6-benzyloxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran 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: 87.0%

benzyl bromide (100-39-0) + Acetic acid (S)-6-hydroxy-2,5,7,8-tetramethyl-chroman-2-ylmethyl ester (163037-44-3) → (S)-(+)-2-acetoxymethyl-6-benzyloxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran (262849-34-3)

Guidance literature:

With cesium fluoride; In tetrahydrofuran; at 60 ℃; for 12h;

DOI:10.1248/cpb.48.272

Reference yield: 35.0%

vinyl acetate (108-05-4,9003-20-7) + (6-Benzyloxy-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl)methanol (171270-07-8) → (S)-(+)-2-acetoxymethyl-6-benzyloxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran (262849-34-3) + (R)-(+)-6-benzyloxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-ylmethanol (188416-16-2)

Guidance literature:

With Burkholderia cepacia Amano PS lipase; at 20 ℃; optical yield given as %ee; enantioselective reaction; Ionic liquid; Enzymatic reaction;

DOI:10.3998/ark.5550190.0012.805

Reference yield:

trolox (56305-04-5,53188-07-1) → (S)-(+)-2-acetoxymethyl-6-benzyloxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran (262849-34-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 98 percent / diethyl ether

2.1: 93 percent / K₂CO₃ / acetone / 12 h / Heating

3.1: 99 percent / LiAlH₄ / diethyl ether / 0.5 h

4.1: H₂ / 20 percent Pd(OH)2/C / ethyl acetate / 20 °C / 15200 Torr

4.2: Lipase PL-266 / diisopropyl ether / 6 h / 33 °C

5.1: 87 percent / CsF / tetrahydrofuran / 12 h / 60 °C

With lithium aluminium tetrahydride; hydrogen; potassium carbonate; cesium fluoride; palladium dihydroxide; In tetrahydrofuran; diethyl ether; ethyl acetate; acetone;

DOI:10.1248/cpb.48.272

upstream raw materials:

benzyl bromide

Acetic acid (S)-6-hydroxy-2,5,7,8-tetramethyl-chroman-2-ylmethyl ester

trolox

methyl 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylate

Downstream raw materials:

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

(+) (S)-6-benzyloxy-2,5,7,8-tetramethyl-chroman-2-carbaldhyde

(S)-6-benzyloxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-ylmethyl (R)-α-methoxy-α-phenyl-α-trifluoromethylacetate

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