(1R,5S,8S,12R)-5-(benzyloxymethyl)-12-cyano-6-aza-7-oxatricyclo[6.3.1.0^1,6]dodecane

Base Information

• Chemical Name: (1R,5S,8S,12R)-5-(benzyloxymethyl)-12-cyano-6-aza-7-oxatricyclo[6.3.1.0^1,6]dodecane
• CAS No.: 233757-56-7
• Molecular Formula: C₁₉H₂₄N₂O₂
• Molecular Weight: 312.412

Synonyms:(1R,5S,8S,12R)-5-(benzyloxymethyl)-12-cyano-6-aza-7-oxatricyclo[6.3.1.0^1,6]dodecane

Chemical Property of (1R,5S,8S,12R)-5-(benzyloxymethyl)-12-cyano-6-aza-7-oxatricyclo[6.3.1.0^1,6]dodecane

Chemical Property:

Purity/Quality:

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Technology Process of (1R,5S,8S,12R)-5-(benzyloxymethyl)-12-cyano-6-aza-7-oxatricyclo[6.3.1.0^1,6]dodecane

There total 19 articles about (1R,5S,8S,12R)-5-(benzyloxymethyl)-12-cyano-6-aza-7-oxatricyclo[6.3.1.0^1,6]dodecane 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: 82.0%

(2S,6R,8R)-2-(benzyloxymethyl)-6-(5'-cyanopent-4'-en-1'-yl)-8-phenyl-1-aza-9-oxabicyclo[4.3.0]nonane → (1R,5S,8S,12S)-8-(benzyloxymethyl)-12-cyano-7-aza-6-oxatricyclo[5.4.11,5.0]undecane + (1R,5S,8S,12R)-5-(benzyloxymethyl)-12-cyano-6-aza-7-oxatricyclo[6.3.1.01,6]dodecane (233757-56-7)

Guidance literature:

In toluene; at 190 ℃; for 3.5h; Inert atmosphere;

DOI:10.1039/c2ob26333e DOI:10.1039/c2ob26333e

Reference yield: 82.0%

(2S,6R,8R)-2-(benzyloxymethyl)-6-(5'-cyanopent-4'-en-1'-yl)-8-phenyl-1-aza-9-oxabicyclo[4.3.0]nonane → (1R,5S,8S,12R)-5-(benzyloxymethyl)-12-cyano-6-aza-7-oxatricyclo[6.3.1.01,6]dodecane (233757-56-7)

Guidance literature:

In toluene; at 190 ℃; for 3.5h;

DOI:10.1039/b200328g

Reference yield:

pent-1-yn-5-ol (5390-04-5) → (1R,5S,8S,12R)-5-(benzyloxymethyl)-12-cyano-6-aza-7-oxatricyclo[6.3.1.01,6]dodecane (233757-56-7)

Guidance literature:

Multi-step reaction with 15 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: NaH / tetrahydrofuran / 19 h / 40 °C

11.2: 517 mg / tetrahydrofuran / 96 h / 40 °C

12.1: 91 percent / aq. HF / acetonitrile / 25 °C

13.1: 100 percent / 2-iodoxybenzoic acid / dimethylsulfoxide

14.1: n-BuLi / tetrahydrofuran; hexane / -78 °C

14.2: B(O-i-Pr)3 / tetrahydrofuran; hexane / -78 °C

14.3: 84 percent / tetrahydrofuran; hexane / -78 °C

15.1: 82 percent / toluene / 3.5 h / 190 °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; sodium hydride; triethylamine; hydroquinone; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; acetone; toluene; acetonitrile;

DOI:10.1039/b200328g

upstream raw materials:

pent-1-yn-5-ol

5-(benzyloxy)-1-pentanol

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

tert-butyl-pent-4-ynyloxy-diphenyl-silane

Downstream raw materials:

(-)-histrionicotoxin

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