[(R)-6-Benzyloxy-5,7,8-trimethyl-2-(tetrahydro-pyran-2-yloxymethyl)-chroman-2-yl]-methanol

Base Information

• Chemical Name: [(R)-6-Benzyloxy-5,7,8-trimethyl-2-(tetrahydro-pyran-2-yloxymethyl)-chroman-2-yl]-methanol
• CAS No.: 105857-83-8
• Molecular Formula: C₂₆H₃₄O₅
• Molecular Weight: 426.553
• Mol file: 105857-83-8.mol

Synonyms:[(R)-6-Benzyloxy-5,7,8-trimethyl-2-(tetrahydro-pyran-2-yloxymethyl)-chroman-2-yl]-methanol

Chemical Property of [(R)-6-Benzyloxy-5,7,8-trimethyl-2-(tetrahydro-pyran-2-yloxymethyl)-chroman-2-yl]-methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(R)-6-Benzyloxy-5,7,8-trimethyl-2-(tetrahydro-pyran-2-yloxymethyl)-chroman-2-yl]-methanol

There total 6 articles about [(R)-6-Benzyloxy-5,7,8-trimethyl-2-(tetrahydro-pyran-2-yloxymethyl)-chroman-2-yl]-methanol 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:

2-{(1R,2S,5R)-1-[(R)-6-Benzyloxy-5,7,8-trimethyl-2-(tetrahydro-pyran-2-yloxymethyl)-chroman-2-ylmethoxy]-2-isopropyl-5-methyl-cyclohexyl}-1-phenyl-ethanone (105857-82-7) → [(R)-6-Benzyloxy-5,7,8-trimethyl-2-(tetrahydro-pyran-2-yloxymethyl)-chroman-2-yl]-methanol (105857-83-8)

Guidance literature:

With potassium hexamethylsilazane; In tetrahydrofuran; at -85 - 20 ℃; Yield given;

DOI:10.1021/ja00236a034

Reference yield:

3,4-dihydro-2H-pyran (110-87-2) → [(R)-6-Benzyloxy-5,7,8-trimethyl-2-(tetrahydro-pyran-2-yloxymethyl)-chroman-2-yl]-methanol (105857-83-8)

Guidance literature:

Multi-step reaction with 2 steps

1: p-TsOH / CH₂Cl₂ / 16 h / Ambient temperature

2: KN(SiMe₃)2 / tetrahydrofuran / -85 - 20 °C

With potassium hexamethylsilazane; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja00236a034

Reference yield:

5,7,8-Trimethyl-6-trimethylsilanyloxy-2,2-bis-trimethylsilanyloxymethyl-chroman (105857-78-1) → [(R)-6-Benzyloxy-5,7,8-trimethyl-2-(tetrahydro-pyran-2-yloxymethyl)-chroman-2-yl]-methanol (105857-83-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 1) TMSOTf, 2) pyridine, 0.5percent NaOH in MeOH / 1) -85 deg C, 2) RT, 1 h

2: 67 percent / TiCl₄ / CH₂Cl₂ / -85 °C

3: 1) nBu₄NF / 1) THF, 30 min, RT, 2) THF, 2 h

4: p-TsOH / CH₂Cl₂ / 16 h / Ambient temperature

5: KN(SiMe₃)2 / tetrahydrofuran / -85 - 20 °C

With pyridine; sodium hydroxide; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; titanium tetrachloride; potassium hexamethylsilazane; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja00236a034

upstream raw materials:

2-{(1R,2S,5R)-1-[(R)-6-Benzyloxy-5,7,8-trimethyl-2-(tetrahydro-pyran-2-yloxymethyl)-chroman-2-ylmethoxy]-2-isopropyl-5-methyl-cyclohexyl}-1-phenyl-ethanone

3,4-dihydro-2H-pyran

5,7,8-Trimethyl-6-trimethylsilanyloxy-2,2-bis-trimethylsilanyloxymethyl-chroman

2-[(1R,2S,5R)-1-((S)-2-Hydroxymethyl-5,7,8-trimethyl-6-trimethylsilanyloxy-chroman-2-ylmethoxy)-2-isopropyl-5-methyl-cyclohexyl]-1-phenyl-ethanone

Downstream raw materials:

(S)-6-Benzyloxy-2,5,7,8-tetramethyl-2-(tetrahydro-pyran-2-yloxymethyl)-chroman

(+) (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-ylmethanol