(1S,2S,3R,5S)-2-methyl-5-(1-methylethenyl)-3-(phenylseleno)-cyclohexanol tetrahydropyranyl ether

Base Information

• Chemical Name: (1S,2S,3R,5S)-2-methyl-5-(1-methylethenyl)-3-(phenylseleno)-cyclohexanol tetrahydropyranyl ether
• CAS No.: 97691-00-4
• Molecular Formula: C₂₁H₃₀O₂Se
• Molecular Weight: 393.428
• Mol file: 97691-00-4.mol

Synonyms:(1S,2S,3R,5S)-2-methyl-5-(1-methylethenyl)-3-(phenylseleno)-cyclohexanol tetrahydropyranyl ether

Chemical Property of (1S,2S,3R,5S)-2-methyl-5-(1-methylethenyl)-3-(phenylseleno)-cyclohexanol tetrahydropyranyl ether

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,3R,5S)-2-methyl-5-(1-methylethenyl)-3-(phenylseleno)-cyclohexanol tetrahydropyranyl ether

There total 3 articles about (1S,2S,3R,5S)-2-methyl-5-(1-methylethenyl)-3-(phenylseleno)-cyclohexanol tetrahydropyranyl ether 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:

(2S,3R,5S)-2-methyl-5-(1-methylethenyl)-3-(phenylseleno)-cyclohexanone (76339-71-4) → (1S,2S,3R,5S)-2-methyl-5-(1-methylethenyl)-3-(phenylseleno)-cyclohexanol tetrahydropyranyl ether (97691-00-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / diisobutylaluminum hydride (DIBAH) / toluene / 3 h / -78 °C

2: PPTS / CH₂Cl₂ / 16 h / Ambient temperature

With pyridinium p-toluenesulfonate; diisobutylaluminium hydride; In dichloromethane; toluene;

DOI:10.1021/jo00218a026

Reference yield:

3,4-dihydro-2H-pyran (110-87-2) + (1S,2S,3R,5S)-2-methyl-5-(1-methylethenyl)-3-(phenylseleno)-cyclohexanol (90056-25-0) → (1S,2S,3R,5S)-2-methyl-5-(1-methylethenyl)-3-(phenylseleno)-cyclohexanol tetrahydropyranyl ether (97691-00-4)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane; for 16h; Ambient temperature;

DOI:10.1021/jo00218a026

Reference yield:

diphenyl diselenide (1666-13-3) → (1S,2S,3R,5S)-2-methyl-5-(1-methylethenyl)-3-(phenylseleno)-cyclohexanol tetrahydropyranyl ether (97691-00-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) NaBH₄, acetic acid / 1) EtOH, 0 deg C, 1 h, 2) EtOH, 3 h

2: 78.5 percent / LiAlH₄ / diethyl ether / 0.08 h / 0 °C

3: 1.02 g / pyridinium p-toluenesulfonate / CH₂Cl₂ / 7 h / Ambient temperature

With sodium tetrahydroborate; lithium aluminium tetrahydride; pyridinium p-toluenesulfonate; acetic acid; In diethyl ether; dichloromethane;

DOI:10.1248/cpb.39.2514

upstream raw materials:

3,4-dihydro-2H-pyran

(1S,2S,3R,5S)-2-methyl-5-(1-methylethenyl)-3-(phenylseleno)-cyclohexanol

(2S,3R,5S)-2-methyl-5-(1-methylethenyl)-3-(phenylseleno)-cyclohexanone

diphenyl diselenide

Downstream raw materials:

(4S,5R)-4-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone

(1S,2R,5S)-2-methyl-5-(1-methylethenyl)-3-cyclohexen-1-ol

(1S,2R,5S)-2-methyl-5-(1-methylethenyl)-1-((tetrahydropyran-2-yl)oxy)-3-cyclohexene

(2R,3R,4S)-3-formyl-2-<2-(methoxycarbonyl)propyl>-4-methyl-3-phenylseleneo-tetrahydrofuran