(2S,3R)-3-Benzyloxy-2-methyl-2-[4-methyl-5-(tetrahydro-pyran-2-yloxy)-pentyl]-cyclohexanone

Base Information

• Chemical Name: (2S,3R)-3-Benzyloxy-2-methyl-2-[4-methyl-5-(tetrahydro-pyran-2-yloxy)-pentyl]-cyclohexanone
• CAS No.: 77514-11-5
• Molecular Formula: C₂₅H₃₈O₄
• Molecular Weight: 402.574
• Mol file: 77514-11-5.mol

Synonyms:(2S,3R)-3-Benzyloxy-2-methyl-2-[4-methyl-5-(tetrahydro-pyran-2-yloxy)-pentyl]-cyclohexanone

Chemical Property of (2S,3R)-3-Benzyloxy-2-methyl-2-[4-methyl-5-(tetrahydro-pyran-2-yloxy)-pentyl]-cyclohexanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-3-Benzyloxy-2-methyl-2-[4-methyl-5-(tetrahydro-pyran-2-yloxy)-pentyl]-cyclohexanone

There total 12 articles about (2S,3R)-3-Benzyloxy-2-methyl-2-[4-methyl-5-(tetrahydro-pyran-2-yloxy)-pentyl]-cyclohexanone 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: 90.0%

3,4-dihydro-2H-pyran (110-87-2) + (2S,3R)-3-Benzyloxy-2-(5-hydroxy-4-methyl-pentyl)-2-methyl-cyclohexanone (77514-10-4) → (2S,3R)-3-Benzyloxy-2-methyl-2-[4-methyl-5-(tetrahydro-pyran-2-yloxy)-pentyl]-cyclohexanone (77514-11-5)

Guidance literature:

With toluene-4-sulfonic acid; In diethyl ether;

DOI:10.1016/S0040-4039(01)81818-9

Reference yield:

(2S,3R)-3-Benzyloxy-2-but-3-ynyl-2-methyl-cyclohexanone (77514-02-4) → (2S,3R)-3-Benzyloxy-2-methyl-2-[4-methyl-5-(tetrahydro-pyran-2-yloxy)-pentyl]-cyclohexanone (77514-11-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 95 percent / TsOH / benzene

2: 1.) 9-BBN 2.) 30percent H₂O₂ , 3N NaOH / 1.) THF

3: 97 percent / diethyl ether

4: 85 percent / CrO₃ , pyridine / CH₂Cl₂

5: 1.) NaH / 1.) DMSO

6: 1.) 9-BBN 2.) 30percent H₂O₂, 3N NaOH / 1.) THF

7: 99 percent / acetone , 2E-3N H₂SO₄

8: 90 percent / TsOH / diethyl ether

With pyridine; chromium(VI) oxide; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; sulfuric acid; dihydrogen peroxide; sodium hydride; toluene-4-sulfonic acid; acetone; In diethyl ether; dichloromethane; benzene;

DOI:10.1016/S0040-4039(01)81818-9

Reference yield:

(4aR,5S)-5-Benzyloxy-4a-methyl-hexahydro-1-oxa-cyclopropa[d]naphthalen-2-one (77514-00-2,80875-95-2,80923-92-8) → (2S,3R)-3-Benzyloxy-2-methyl-2-[4-methyl-5-(tetrahydro-pyran-2-yloxy)-pentyl]-cyclohexanone (77514-11-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 83 percent / p-TsNHNH₂ , AcOH / CH₂Cl₂

2: 95 percent / TsOH / benzene

3: 1.) 9-BBN 2.) 30percent H₂O₂ , 3N NaOH / 1.) THF

4: 97 percent / diethyl ether

5: 85 percent / CrO₃ , pyridine / CH₂Cl₂

6: 1.) NaH / 1.) DMSO

7: 1.) 9-BBN 2.) 30percent H₂O₂, 3N NaOH / 1.) THF

8: 99 percent / acetone , 2E-3N H₂SO₄

9: 90 percent / TsOH / diethyl ether

With pyridine; chromium(VI) oxide; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; sulfuric acid; dihydrogen peroxide; sodium hydride; toluene-4-sulfonic acid; acetic acid; toluene-4-sulfonic acid hydrazide; acetone; In diethyl ether; dichloromethane; benzene;

DOI:10.1016/S0040-4039(01)81818-9

upstream raw materials:

3,4-dihydro-2H-pyran

(2S,3R)-3-Benzyloxy-2-(5-hydroxy-4-methyl-pentyl)-2-methyl-cyclohexanone

(2S,3R)-3-Benzyloxy-2-but-3-ynyl-2-methyl-cyclohexanone

(4aS,5S)-5-Benzyloxy-4a-methyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one

Downstream raw materials:

(6R,7S)-6-Benzyloxy-7-methyl-7-[4-methyl-5-(tetrahydro-pyran-2-yloxy)-pentyl]-oxepan-2-one

(2R,3S)-3-Benzyloxy-2-methyl-2-[4-methyl-5-(tetrahydro-pyran-2-yloxy)-pentyl]-2,3,4,5-tetrahydro-oxepine

(6R,7S)-6-Benzyloxy-7-methyl-7-[4-methyl-5-(tetrahydro-pyran-2-yloxy)-pentyl]-oxepan-3-ol

(6R,7S)-6-Benzyloxy-7-methyl-7-[4-methyl-5-(tetrahydro-pyran-2-yloxy)-pentyl]-oxepan-3-one