(1R,2S,6S,7S)-2-Benzyloxymethyl-5-oxo-bicyclo[4.2.0]octane-7-carboxylic acid methyl ester

Base Information

Chemical Name:(1R,2S,6S,7S)-2-Benzyloxymethyl-5-oxo-bicyclo[4.2.0]octane-7-carboxylic acid methyl ester
CAS No.:573699-34-0
Molecular Formula:C₁₈H₂₂O₄
Molecular Weight:302.37
Hs Code.:

Synonyms:(1R,2S,6S,7S)-2-Benzyloxymethyl-5-oxo-bicyclo[4.2.0]octane-7-carboxylic acid methyl ester

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Chemical Property of (1R,2S,6S,7S)-2-Benzyloxymethyl-5-oxo-bicyclo[4.2.0]octane-7-carboxylic acid methyl ester

Chemical Property:

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Technology Process of (1R,2S,6S,7S)-2-Benzyloxymethyl-5-oxo-bicyclo[4.2.0]octane-7-carboxylic acid methyl ester

There total 1 articles about (1R,2S,6S,7S)-2-Benzyloxymethyl-5-oxo-bicyclo[4.2.0]octane-7-carboxylic acid methyl ester 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:

: 573699-05-5
(-)-4-((Benzyloxy)methyl)-2-cyclohexen-1-one

: 292638-85-8,9003-21-8,96-33-3
acrylic acid methyl ester

: 573699-34-0
(1R,2S,6S,7S)-2-Benzyloxymethyl-5-oxo-bicyclo[4.2.0]octane-7-carboxylic acid methyl ester

Guidance literature:: In dichloromethane; at 0 ℃; for 8.5h; Irradiation;
DOI:10.1021/ja034842k

Reference yield:

: 573699-34-0
(1R,2S,6S,7S)-2-Benzyloxymethyl-5-oxo-bicyclo[4.2.0]octane-7-carboxylic acid methyl ester

: 314280-86-9
C₄₅H₅₂N₂O₇Se

Guidance literature:: Multi-step reaction with 23 steps

1.1: Amberlyst-15 ion exchange resin / 2.5 h / 0 °C

2.1: diethyl ether; benzene / 1.5 h / 20 °C

3.1: pyridinium p-toluenesulfonate / acetone / 2.25 h / 20 °C

4.1: i-Pr₂NEt / CH₂Cl₂ / 70 h / 20 °C

5.1: sodium hydride / tetrahydrofuran / 3 h / 20 °C

5.2: aq. HCl / tetrahydrofuran / pH 5

6.1: Et₃N / tetrahydrofuran / 7 h / 0 - 20 °C

7.1: aq. potassium hydroxide / methanol / Heating

8.1: 83 percent / hydroxylamine hydrochloride; sodium acetate / methanol / 3 h / Heating

9.1: xylene / 4.5 h / 110 °C

10.1: sodium hydroxide / aq. ethanol / Heating

11.1: H₂ / Pd(OH)2/C / ethanol; methanol; propan-2-ol / 48 h

12.1: i-Pr₂NEt; DMAP / CH₂Cl₂ / 3 h / 20 °C

13.1: aq. HCl / methanol / 3 h / 20 °C

14.1: DMAP; Et₃N / CH₂Cl₂ / 25 h / 20 °C

15.1: 48 percent / DMAP; Et₃N / tetrahydrofuran / 48 h / 20 °C

16.1: n-BuLi / diethyl ether; hexane / 0.5 h / 0 °C

16.2: diethyl ether; hexane / 0 °C

17.1: s-BuLi / diethyl ether; hexane; cyclohexane / 0.5 h / 0 °C

17.2: diethyl ether; hexane; tetrahydrofuran / 0.5 h / 0 °C

17.3: 81 percent / silica gel / CHCl₃ / 2 h / 20 °C

18.1: 65 percent / sulfur trioxide pyridine complex; Et₃N / dimethylsulfoxide / 0.5 h / 20 °C

19.1: 89 percent / aq. HCl / tetrahydrofuran / 1 h / 20 °C

20.1: 62 percent / Sc(OTf)3 / benzene / 1 h / 20 °C

21.1: 80 percent / Et₃N; DMAP / CH₂Cl₂ / 1 h / 20 °C

22.1: 84 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C

23.1: 81 percent / Bu₃P / tetrahydrofuran / 0.25 h / 20 °C

With hydrogenchloride; dmap; potassium hydroxide; sodium hydroxide; n-butyllithium; tributylphosphine; Amberlyst-15 ion exchange resin; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; hydrogen; sec.-butyllithium; sodium acetate; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; scandium tris(trifluoromethanesulfonate); palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; cyclohexane; dimethyl sulfoxide; isopropyl alcohol; acetone; xylene; benzene; 9.1: Semmler-Wolff aniline aromatization / 18.1: Parikh-Doering oxidation;
DOI:10.1021/ja034842k

Reference yield:

: 573699-34-0
(1R,2S,6S,7S)-2-Benzyloxymethyl-5-oxo-bicyclo[4.2.0]octane-7-carboxylic acid methyl ester

: 118378-03-3
(1S,5S,6R,8S)-5-Benzyloxymethyl-8-(1-hydroxy-1-methyl-ethyl)-bicyclo[4.2.0]octan-2-one

Guidance literature:: Multi-step reaction with 3 steps

1: Amberlyst-15 ion exchange resin / 2.5 h / 0 °C

2: diethyl ether; benzene / 1.5 h / 20 °C

3: pyridinium p-toluenesulfonate / acetone / 2.25 h / 20 °C

With Amberlyst-15 ion exchange resin; pyridinium p-toluenesulfonate; In diethyl ether; acetone; benzene;
DOI:10.1021/ja034842k