(2S,6R,8R)-2-(benzyloxymethyloxymethyl)-6-(4'-hydroxy-1'-butyl)-8-phenyl-1-aza-9-oxabicyclo[4.3.0]nonane

Base Information

• Chemical Name: (2S,6R,8R)-2-(benzyloxymethyloxymethyl)-6-(4'-hydroxy-1'-butyl)-8-phenyl-1-aza-9-oxabicyclo[4.3.0]nonane
• CAS No.: 473543-01-0
• Molecular Formula: C₂₆H₃₅NO₄
• Molecular Weight: 425.568

Synonyms:(2S,6R,8R)-2-(benzyloxymethyloxymethyl)-6-(4'-hydroxy-1'-butyl)-8-phenyl-1-aza-9-oxabicyclo[4.3.0]nonane

Chemical Property of (2S,6R,8R)-2-(benzyloxymethyloxymethyl)-6-(4'-hydroxy-1'-butyl)-8-phenyl-1-aza-9-oxabicyclo[4.3.0]nonane

Chemical Property:

Purity/Quality:

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Technology Process of (2S,6R,8R)-2-(benzyloxymethyloxymethyl)-6-(4'-hydroxy-1'-butyl)-8-phenyl-1-aza-9-oxabicyclo[4.3.0]nonane

There total 15 articles about (2S,6R,8R)-2-(benzyloxymethyloxymethyl)-6-(4'-hydroxy-1'-butyl)-8-phenyl-1-aza-9-oxabicyclo[4.3.0]nonane 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: 89.0%

(2S,6R,8R)-2-(benzyloxymethyloxymethyl)-6-(4'-tert-butyldiphenylsilyloxy-1'-butyl)-8-phenyl-1-aza-9-oxabicyclo[4.3.0]nonane (473543-00-9) → (2S,6R,8R)-2-(benzyloxymethyloxymethyl)-6-(4'-hydroxy-1'-butyl)-8-phenyl-1-aza-9-oxabicyclo[4.3.0]nonane (473543-01-0)

Guidance literature:

With hydrogen fluoride; In acetonitrile; at 25 ℃;

DOI:10.1039/b200328g

Reference yield:

pent-1-yn-5-ol (5390-04-5) → (2S,6R,8R)-2-(benzyloxymethyloxymethyl)-6-(4'-hydroxy-1'-butyl)-8-phenyl-1-aza-9-oxabicyclo[4.3.0]nonane (473543-01-0)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 100 percent / imidazole / CH₂Cl₂ / 25 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 1.25 h / -50 °C

2.2: 90 percent / tetrahydrofuran; hexane / 96 h / 50 °C

3.1: 100 percent / BCl₃*SMe₂ / CH₂Cl₂

4.1: 98 percent / CrO₃; H₂SO₄ / acetone / 3 h / 0 °C

5.1: Et₃N / tetrahydrofuran / 1 h / 25 °C

6.1: n-BuLi; pyren-1-ylacetic acid / tetrahydrofuran; hexane / 0.33 h / -78 °C

6.2: 3.54 g / tetrahydrofuran; hexane / 1.5 h / 25 °C

7.1: NaHMDS / tetrahydrofuran / 0.02 h / -78 °C

7.2: 1-chloro-1-nitrosocyclohexane / tetrahydrofuran / 0.5 h / -78 °C

7.3: 77 percent / aq. HCl / tetrahydrofuran / 1 h / 25 °C

8.1: toluene / 7 h / 75 °C

9.1: 2.7 g / quinol / 6 h / 80 °C

10.1: LiAlH₄ / tetrahydrofuran / 3.5 h / 0 °C

11.1: nBu₄NI; (i-Pr)2NEt / toluene / 4.5 h / 60 °C

11.2: 1.06 g / nBu₄NI; (i-Pr)2NEt / toluene / 4.5 h / 60 °C

12.1: 89 percent / aq. HF / acetonitrile / 25 °C

With 1H-imidazole; chromium(VI) oxide; lithium aluminium tetrahydride; n-butyllithium; boron trichloride - methyl sulfide complex; sulfuric acid; 1-pyreneacetic acid; hydrogen fluoride; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; triethylamine; N-ethyl-N,N-diisopropylamine; hydroquinone; In tetrahydrofuran; hexane; dichloromethane; acetone; toluene; acetonitrile;

DOI:10.1039/b200328g

Reference yield:

5-(benzyloxy)-1-pentanol (4541-15-5) → (2S,6R,8R)-2-(benzyloxymethyloxymethyl)-6-(4'-hydroxy-1'-butyl)-8-phenyl-1-aza-9-oxabicyclo[4.3.0]nonane (473543-01-0)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 88 percent / Et₃N; DMAP / CH₂Cl₂ / 3 h / 25 °C

2.1: 85 percent / NaI / acetone / 62 h / 25 °C

3.1: n-BuLi / tetrahydrofuran; hexane / 1.25 h / -50 °C

3.2: 90 percent / tetrahydrofuran; hexane / 96 h / 50 °C

4.1: 100 percent / BCl₃*SMe₂ / CH₂Cl₂

5.1: 98 percent / CrO₃; H₂SO₄ / acetone / 3 h / 0 °C

6.1: Et₃N / tetrahydrofuran / 1 h / 25 °C

7.1: n-BuLi; pyren-1-ylacetic acid / tetrahydrofuran; hexane / 0.33 h / -78 °C

7.2: 3.54 g / tetrahydrofuran; hexane / 1.5 h / 25 °C

8.1: NaHMDS / tetrahydrofuran / 0.02 h / -78 °C

8.2: 1-chloro-1-nitrosocyclohexane / tetrahydrofuran / 0.5 h / -78 °C

8.3: 77 percent / aq. HCl / tetrahydrofuran / 1 h / 25 °C

9.1: toluene / 7 h / 75 °C

10.1: 2.7 g / quinol / 6 h / 80 °C

11.1: LiAlH₄ / tetrahydrofuran / 3.5 h / 0 °C

12.1: nBu₄NI; (i-Pr)2NEt / toluene / 4.5 h / 60 °C

12.2: 1.06 g / nBu₄NI; (i-Pr)2NEt / toluene / 4.5 h / 60 °C

13.1: 89 percent / aq. HF / acetonitrile / 25 °C

With chromium(VI) oxide; dmap; lithium aluminium tetrahydride; n-butyllithium; boron trichloride - methyl sulfide complex; sulfuric acid; 1-pyreneacetic acid; hydrogen fluoride; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; triethylamine; N-ethyl-N,N-diisopropylamine; hydroquinone; sodium iodide; In tetrahydrofuran; hexane; dichloromethane; acetone; toluene; acetonitrile; 2.1: Finkelstein reaction;

DOI:10.1039/b200328g

upstream raw materials:

(2S,6R,8R)-2-(benzyloxymethyloxymethyl)-6-(4'-tert-butyldiphenylsilyloxy-1'-butyl)-8-phenyl-1-aza-9-oxabicyclo[4.3.0]nonane

pent-1-yn-5-ol

5-(benzyloxy)-1-pentanol

(((5-iodopentyl)oxy)methyl)benzene

Downstream raw materials:

(2S,6R,8R)-2-(benzyloxymethyloxymethyl)-6-(3'-formyl-1'-propyl)-8-phenyl-1-aza-9-oxabicyclo[4.3.0]nonane

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