1-benzyloxy-5-(4-methoxy-benzyloxy)-9-(tetrahydro-pyran-2-yloxy)-non-7-en-4-ol

Base Information

• Chemical Name: 1-benzyloxy-5-(4-methoxy-benzyloxy)-9-(tetrahydro-pyran-2-yloxy)-non-7-en-4-ol
• CAS No.: 934977-35-2
• Molecular Formula: C₂₉H₄₀O₆
• Molecular Weight: 484.633
• Mol file: 934977-35-2.mol

Synonyms:1-benzyloxy-5-(4-methoxy-benzyloxy)-9-(tetrahydro-pyran-2-yloxy)-non-7-en-4-ol

Chemical Property of 1-benzyloxy-5-(4-methoxy-benzyloxy)-9-(tetrahydro-pyran-2-yloxy)-non-7-en-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-benzyloxy-5-(4-methoxy-benzyloxy)-9-(tetrahydro-pyran-2-yloxy)-non-7-en-4-ol

There total 1 articles about 1-benzyloxy-5-(4-methoxy-benzyloxy)-9-(tetrahydro-pyran-2-yloxy)-non-7-en-4-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: 87.0%

2-(4-methoxy-benzyloxy)-6-(tetrahydro-pyran-2-yloxy)-hex-4-enoic acid methyl ester (934977-34-1) + 3-benzyloxypropylmagnesium bromide (183312-54-1) → 1-benzyloxy-5-(4-methoxy-benzyloxy)-9-(tetrahydro-pyran-2-yloxy)-non-7-en-4-ol (934977-35-2)

Guidance literature:

2-(4-methoxy-benzyloxy)-6-(tetrahydro-pyran-2-yloxy)-hex-4-enoic acid methyl ester; With diisobutylaluminium hydride; In diethyl ether; hexane; at -78 - 20 ℃; for 0.5h;

3-benzyloxypropylmagnesium bromide; In diethyl ether; hexane; at -30 - -20 ℃; for 12h;

DOI:10.1021/ja068346i

Reference yield: 100.0%

1-benzyloxy-5-(4-methoxy-benzyloxy)-9-(tetrahydro-pyran-2-yloxy)-non-7-en-4-ol (934977-35-2) + 2-chloro-N,N-dimethylacetamide (2675-89-0) → 2-[1-(3-benzyloxy-propyl)-2-(4-methoxy-benzyloxy)-6-(tetrahydro-pyran-2-yloxy)-hex-4-enyloxy]-N,N-dimethyl-acetamide (934977-36-3)

Guidance literature:

1-benzyloxy-5-(4-methoxy-benzyloxy)-9-(tetrahydro-pyran-2-yloxy)-non-7-en-4-ol; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.166667h;

2-chloro-N,N-dimethylacetamide; In tetrahydrofuran; at 20 ℃; for 4h;

DOI:10.1021/ja068346i

Reference yield:

1-benzyloxy-5-(4-methoxy-benzyloxy)-9-(tetrahydro-pyran-2-yloxy)-non-7-en-4-ol (934977-35-2) → 1-[2-(3-benzyloxy-propyl)-7-bromo-3,9-dioxa-bicyclo[4.2.1]non-4-yl]-propan-1-one (934977-14-7)

Guidance literature:

Multi-step reaction with 14 steps

1.1: NaH / tetrahydrofuran / 0.17 h / 0 °C

1.2: 100 percent / tetrahydrofuran / 4 h / 20 °C

2.1: 97 percent / ethanol / PTSA / 3 h / 20 °C

3.1: 92 percent / Ph₃P; CCl₄ / 2 h / Heating

4.1: 89 percent / KHMDS / toluene / 0.5 h / 20 °C

5.1: 99 percent / DDQ / CH₂Cl₂; H₂O / 2 h / 20 °C / pH 7.0 / buffered reaction

6.1: CCl₄; 1-methylcyclohexene; tri-n-octylphosphine / toluene / 12 h / 70 °C

7.1: 430.0 mg / NMO / OsO₄ / acetone; H₂O / 4 h / 0 °C

8.1: 98 percent / NaH / tetrahydrofuran / 12 h / 20 °C

9.1: 92 percent / NMO / TPAP / CH₂Cl₂ / 3 h / 20 °C

10.1: KHMDS / toluene; tetrahydrofuran / 0.5 h / -78 °C

10.2: 94 percent / toluene; tetrahydrofuran / 1 h / -78 °C

11.1: lithium chloride / Pd(PPh₃)4 / tetrahydrofuran / 3 h / Heating

11.2: 75 percent / Br₂ / tetrahydrofuran; CH₂Cl₂ / 1 h / -20 °C

12.1: 88 percent / p-toluenesulfonyl hydrazide / xylene / 2 h / 140 °C

13.1: 86 percent / tetrahydrofuran / 1 h / 20 °C

14.1: 75 percent / KOH / tetrahydrofuran; methanol; H₂O / 48 h / 20 °C

With tetrachloromethane; potassium hydroxide; N-methyl-2-indolinone; 1-methylcyclohex-1-ene; ethanol; TOP; potassium hexamethylsilazane; sodium hydride; toluene-4-sulfonic acid hydrazide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrapropylammonium perruthennate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; water; acetone; toluene; xylene;

DOI:10.1021/ja068346i

upstream raw materials:

2-(4-methoxy-benzyloxy)-6-(tetrahydro-pyran-2-yloxy)-hex-4-enoic acid methyl ester

3-benzyloxypropylmagnesium bromide

Downstream raw materials:

2-[1-(3-benzyloxy-propyl)-2-(4-methoxy-benzyloxy)-6-(tetrahydro-pyran-2-yloxy)-hex-4-enyloxy]-N,N-dimethyl-acetamide

2-(3-benzyloxy-propyl)-7-bromo-3,9-dioxa-bicyclo[4.2.1]non-7-ene-4-carboxylic acid dimethylamide

1-[2-(3-benzyloxy-propyl)-7-bromo-3,9-dioxa-bicyclo[4.2.1]non-4-yl]-propan-1-one

1-[2-(3-benzyloxy-propyl)-7-bromo-3,9-dioxa-bicyclo[4.2.1]non-4-yl]-propan-1-one

Refernces