6-[4-hydroxy-6-(4-methoxy-benzyloxy)-1,5-dimethyl-hexyl]-5-methyl-5,6-dihydro-2H-pyran-2-ol

Base Information

• Chemical Name: 6-[4-hydroxy-6-(4-methoxy-benzyloxy)-1,5-dimethyl-hexyl]-5-methyl-5,6-dihydro-2H-pyran-2-ol
• CAS No.: 924286-84-0
• Molecular Formula: C₂₂H₃₄O₅
• Molecular Weight: 378.509
• Mol file: 924286-84-0.mol

Synonyms:6-[4-hydroxy-6-(4-methoxy-benzyloxy)-1,5-dimethyl-hexyl]-5-methyl-5,6-dihydro-2H-pyran-2-ol

Chemical Property of 6-[4-hydroxy-6-(4-methoxy-benzyloxy)-1,5-dimethyl-hexyl]-5-methyl-5,6-dihydro-2H-pyran-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-[4-hydroxy-6-(4-methoxy-benzyloxy)-1,5-dimethyl-hexyl]-5-methyl-5,6-dihydro-2H-pyran-2-ol

There total 12 articles about 6-[4-hydroxy-6-(4-methoxy-benzyloxy)-1,5-dimethyl-hexyl]-5-methyl-5,6-dihydro-2H-pyran-2-ol 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)-3,4-(pentane-3,3-diyl)dioxy-2-methylbutan-1-ol (924286-09-9) → 6-[4-hydroxy-6-(4-methoxy-benzyloxy)-1,5-dimethyl-hexyl]-5-methyl-5,6-dihydro-2H-pyran-2-ol (924286-84-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 80 percent / NaH; Bu₄NI / tetrahydrofuran / 20 h / 0 - 25 °C

2.1: 5.80 g / p-TsOH*H₂O / methanol / 7 h / 25 °C

3.1: NaH / tetrahydrofuran / 1 h / 0 °C

3.2: 4.41 g / 1-(p-toluenesulfonyl)imidazole / tetrahydrofuran / 4 h / -78 - 25 °C

4.1: t-BuLi / pentane; diethyl ether / 0.08 h / -78 °C

4.2: (2-Th)CuCNLi / diethyl ether; pentane; tetrahydrofuran / 0.08 h / -78 - 0 °C

4.3: 1.16 g / diethyl ether; pentane; tetrahydrofuran / 1 h / 0 °C

5.1: aq. HCl / acetone / 0.17 h / 25 °C

With hydrogenchloride; tert.-butyl lithium; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; diethyl ether; acetone; pentane;

DOI:10.1021/ja066477d

Reference yield:

(R)-2,2-diethyl-4-[(S)-1-(4-methoxybenzyloxy)propan-2-yl]-1,3-dioxolane (924286-10-2) → 6-[4-hydroxy-6-(4-methoxy-benzyloxy)-1,5-dimethyl-hexyl]-5-methyl-5,6-dihydro-2H-pyran-2-ol (924286-84-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 5.80 g / p-TsOH*H₂O / methanol / 7 h / 25 °C

2.1: NaH / tetrahydrofuran / 1 h / 0 °C

2.2: 4.41 g / 1-(p-toluenesulfonyl)imidazole / tetrahydrofuran / 4 h / -78 - 25 °C

3.1: t-BuLi / pentane; diethyl ether / 0.08 h / -78 °C

3.2: (2-Th)CuCNLi / diethyl ether; pentane; tetrahydrofuran / 0.08 h / -78 - 0 °C

3.3: 1.16 g / diethyl ether; pentane; tetrahydrofuran / 1 h / 0 °C

4.1: aq. HCl / acetone / 0.17 h / 25 °C

With hydrogenchloride; tert.-butyl lithium; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; diethyl ether; acetone; pentane;

DOI:10.1021/ja066477d

Reference yield:

(2S,3R,4S)-3-acryloxy-1-(tert-butyldiphenylsilyloxy)-2,4-dimethylhex-5-ene (924286-00-0) → 6-[4-hydroxy-6-(4-methoxy-benzyloxy)-1,5-dimethyl-hexyl]-5-methyl-5,6-dihydro-2H-pyran-2-ol (924286-84-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 89 percent / Grubbs' I catalyst / CH₂Cl₂ / 12 h / 40 °C

2.1: DIBAL-H / CH₂Cl₂; toluene / 1 h / -78 °C

2.2: PPTS / 0.17 h / 25 °C

3.1: nBu₄NF / tetrahydrofuran / 12 h / 25 °C

4.1: NaH / benzene / 0.75 h

4.2: 5.50 g / benzene / 3 h / 25 °C

5.1: 90 percent / NaI / acetone / 12 h / 56 °C

6.1: t-BuLi / pentane; diethyl ether / 0.08 h / -78 °C

6.2: (2-Th)CuCNLi / diethyl ether; pentane; tetrahydrofuran / 0.08 h / -78 - 0 °C

6.3: 1.16 g / diethyl ether; pentane; tetrahydrofuran / 1 h / 0 °C

7.1: aq. HCl / acetone / 0.17 h / 25 °C

With hydrogenchloride; tetrabutyl ammonium fluoride; tert.-butyl lithium; sodium hydride; diisobutylaluminium hydride; sodium iodide; Grubbs catalyst first generation; In tetrahydrofuran; diethyl ether; dichloromethane; acetone; toluene; pentane; benzene;

DOI:10.1021/ja066477d

upstream raw materials:

(2R,3S)-4-(4-methoxybenzyloxy)-3-methylbutane-1,2-diol

2-(6-methoxy-3-methyl-3,6-dihydro-2H-pyran-2-yl)-propan-1-ol

(2S,3R)-3,4-(pentane-3,3-diyl)dioxy-2-methylbutan-1-ol

(2R,5S,6S)-6-[(1S)-2-iodo-1-methylethyl]-5-methyl-2-methoxy-5,6-dihydro-2H-pyran

Downstream raw materials:

(5S,6S)-6-[(2S,5S,6S)-5-hydroxy-7-(4-methoxybenzyloxy)-6-methylheptan-2-yl]-5-methyl-5,6-dihydropyran-2-one

bis[(9H-fluoren-9-yl)methyl](2S,3S,6S)-1-(4-methoxybenzyloxy)-2-methyl-6-((2S,3S)-3-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)heptan-3-yl phosphate