Bicyclo[4.2.0]octane-7-carboxylic acid, 5,5-dimethoxy-2-[(phenylmethoxy)methyl]-, methyl ester, (1R,2S,6S,7S)-

Base Information

Chemical Name:Bicyclo[4.2.0]octane-7-carboxylic acid, 5,5-dimethoxy-2-[(phenylmethoxy)methyl]-, methyl ester, (1R,2S,6S,7S)-
CAS No.:573699-35-1
Molecular Formula:C20H28O5
Molecular Weight:348.439
Hs Code.:

Synonyms:

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Chemical Property of Bicyclo[4.2.0]octane-7-carboxylic acid, 5,5-dimethoxy-2-[(phenylmethoxy)methyl]-, methyl ester, (1R,2S,6S,7S)-

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Technology Process of Bicyclo[4.2.0]octane-7-carboxylic acid, 5,5-dimethoxy-2-[(phenylmethoxy)methyl]-, methyl ester, (1R,2S,6S,7S)-

There total 2 articles about Bicyclo[4.2.0]octane-7-carboxylic acid, 5,5-dimethoxy-2-[(phenylmethoxy)methyl]-, methyl ester, (1R,2S,6S,7S)- 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

: 573699-35-1
(1R,2S,6S,7S)-2-Benzyloxymethyl-5,5-dimethoxy-bicyclo[4.2.0]octane-7-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: CH₂Cl₂ / 8.5 h / 0 °C / Irradiation

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

With Amberlyst-15 ion exchange resin; In dichloromethane;
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

: 149-73-5
trimethyl orthoformate

: 573699-35-1
(1R,2S,6S,7S)-2-Benzyloxymethyl-5,5-dimethoxy-bicyclo[4.2.0]octane-7-carboxylic acid methyl ester

Guidance literature:: With Amberlyst-15 ion exchange resin; at 0 ℃; for 2.5h;
DOI:10.1021/ja034842k

Reference yield:

: 573699-35-1
(1R,2S,6S,7S)-2-Benzyloxymethyl-5,5-dimethoxy-bicyclo[4.2.0]octane-7-carboxylic acid methyl ester

: 314280-86-9
C₄₅H₅₂N₂O₇Se

Guidance literature:: Multi-step reaction with 22 steps

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

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

3.1: i-Pr₂NEt / CH₂Cl₂ / 70 h / 20 °C

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

4.2: aq. HCl / tetrahydrofuran / pH 5

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

6.1: aq. potassium hydroxide / methanol / Heating

7.1: 83 percent / hydroxylamine hydrochloride; sodium acetate / methanol / 3 h / Heating

8.1: xylene / 4.5 h / 110 °C

9.1: sodium hydroxide / aq. ethanol / Heating

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

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

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

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

14.1: 48 percent / DMAP; Et₃N / tetrahydrofuran / 48 h / 20 °C

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

15.2: diethyl ether; hexane / 0 °C

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

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

16.3: 81 percent / silica gel / CHCl₃ / 2 h / 20 °C

17.1: 65 percent / sulfur trioxide pyridine complex; Et₃N / dimethylsulfoxide / 0.5 h / 20 °C

18.1: 89 percent / aq. HCl / tetrahydrofuran / 1 h / 20 °C

19.1: 62 percent / Sc(OTf)3 / benzene / 1 h / 20 °C

20.1: 80 percent / Et₃N; DMAP / CH₂Cl₂ / 1 h / 20 °C

21.1: 84 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C

22.1: 81 percent / Bu₃P / tetrahydrofuran / 0.25 h / 20 °C

With hydrogenchloride; dmap; potassium hydroxide; sodium hydroxide; n-butyllithium; tributylphosphine; 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; 8.1: Semmler-Wolff aniline aromatization / 17.1: Parikh-Doering oxidation;
DOI:10.1021/ja034842k