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

Base Information

• Chemical Name: (6R,7S)-6-Benzyloxy-7-methyl-7-[4-methyl-5-(tetrahydro-pyran-2-yloxy)-pentyl]-oxepan-3-one
• CAS No.: 77513-81-6
• Molecular Formula: C₂₅H₃₈O₅
• Molecular Weight: 418.574
• Mol file: 77513-81-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 12 articles about (6R,7S)-6-Benzyloxy-7-methyl-7-[4-methyl-5-(tetrahydro-pyran-2-yloxy)-pentyl]-oxepan-3-one 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%

(6R,7S)-6-Benzyloxy-7-methyl-7-[4-methyl-5-(tetrahydro-pyran-2-yloxy)-pentyl]-oxepan-3-ol (77513-80-5) → (6R,7S)-6-Benzyloxy-7-methyl-7-[4-methyl-5-(tetrahydro-pyran-2-yloxy)-pentyl]-oxepan-3-one (77513-81-6)

Guidance literature:

With pyridine; chromium(VI) oxide; In dichloromethane;

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

Reference yield:

3,4-dihydro-2H-pyran (110-87-2) → (6R,7S)-6-Benzyloxy-7-methyl-7-[4-methyl-5-(tetrahydro-pyran-2-yloxy)-pentyl]-oxepan-3-one (77513-81-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 90 percent / TsOH / diethyl ether

2: 70 percent / MCPBA , NaOAc / CH₂Cl₂ / Heating

3: 1.) LDA 2.) TMEDA / 1.) THF , -78 deg C 2.) HMPA

4: 57 percent / Na / 2-methyl-propan-2-ol; liquid ammonia; tetrahydrofuran

5: 98 percent / NaH / benzene

6: 1.) BH₃ 2.)H₂O₂ , NaOH / 1.) THF

7: 90 percent / CrO₃ , pyridine / CH₂Cl₂

With pyridine; chromium(VI) oxide; sodium hydroxide; N,N,N,N,-tetramethylethylenediamine; borane; dihydrogen peroxide; sodium acetate; sodium; sodium hydride; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; ammonia; tert-butyl alcohol; benzene;

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

Reference yield:

(2R,3S)-2-Methyl-2-[4-methyl-5-(tetrahydro-pyran-2-yloxy)-pentyl]-2,3,4,5-tetrahydro-oxepin-3-ol (77513-78-1) → (6R,7S)-6-Benzyloxy-7-methyl-7-[4-methyl-5-(tetrahydro-pyran-2-yloxy)-pentyl]-oxepan-3-one (77513-81-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / NaH / benzene

2: 1.) BH₃ 2.)H₂O₂ , NaOH / 1.) THF

3: 90 percent / CrO₃ , pyridine / CH₂Cl₂

With pyridine; chromium(VI) oxide; sodium hydroxide; borane; dihydrogen peroxide; sodium hydride; In dichloromethane; benzene;

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

upstream raw materials:

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

3,4-dihydro-2H-pyran

(2R,3S)-2-Methyl-2-[4-methyl-5-(tetrahydro-pyran-2-yloxy)-pentyl]-2,3,4,5-tetrahydro-oxepin-3-ol

(6R,7S)-7-Benzyloxy-6-methyl-6-(4-methyl-pent-4-enyl)-1,4-dioxa-spiro[4.5]decane

Downstream raw materials:

(+/-)-zoapatanol

(+/-)-6-(Z)-Zoapatanol

(8S,9R)-9-Benzyloxy-8-[4,8-dimethyl-5-(tetrahydro-pyran-2-yloxy)-non-7-enyl]-8-methyl-1,4,7-trioxa-spiro[4.6]undecane

Acetic acid 1-[4-((8S,9R)-9-benzyloxy-8-methyl-1,4,7-trioxa-spiro[4.6]undec-8-yl)-1-methyl-butyl]-4-methyl-pent-4-enyl ester