((1R,4S,6R)-6-Benzyloxymethyl-4-hydroxy-6-vinyl-cyclohex-2-enyl)-acetic acid methyl ester

Base Information

Chemical Name:((1R,4S,6R)-6-Benzyloxymethyl-4-hydroxy-6-vinyl-cyclohex-2-enyl)-acetic acid methyl ester
CAS No.:467220-01-5
Molecular Formula:C₁₉H₂₄O₄
Molecular Weight:316.397
Hs Code.:

Synonyms:((1R,4S,6R)-6-Benzyloxymethyl-4-hydroxy-6-vinyl-cyclohex-2-enyl)-acetic acid methyl ester

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Chemical Property of ((1R,4S,6R)-6-Benzyloxymethyl-4-hydroxy-6-vinyl-cyclohex-2-enyl)-acetic acid methyl ester

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Technology Process of ((1R,4S,6R)-6-Benzyloxymethyl-4-hydroxy-6-vinyl-cyclohex-2-enyl)-acetic acid methyl ester

There total 9 articles about ((1R,4S,6R)-6-Benzyloxymethyl-4-hydroxy-6-vinyl-cyclohex-2-enyl)-acetic 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: 65.0%

: 467220-00-4
((1R,6R)-6-Benzyloxymethyl-4-oxo-6-vinyl-cyclohex-2-enyl)-acetic acid methyl ester

: 467220-01-5
((1R,4S,6R)-6-Benzyloxymethyl-4-hydroxy-6-vinyl-cyclohex-2-enyl)-acetic acid methyl ester

: ((1R,4R,6R)-6-Benzyloxymethyl-4-hydroxy-6-vinyl-cyclohex-2-enyl)-acetic acid methyl ester

Guidance literature:: With sodium tetrahydroborate; cerium(III) chloride; at -78 ℃;
DOI:10.1055/s-2002-32603

Reference yield:

: 66222-28-4
(benzyloxymethyl)tributylstannane

: 467220-01-5
((1R,4S,6R)-6-Benzyloxymethyl-4-hydroxy-6-vinyl-cyclohex-2-enyl)-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 95 percent / BuLi / tetrahydrofuran / -78 °C

2.1: 75 percent / PCC / CH₂Cl₂

3.1: CuBr*Me₂S / tetrahydrofuran

3.2: HMPA; TMS-Cl / tetrahydrofuran / -78 °C

3.3: 92 percent / TBAF

4.1: 90 percent / aq. HCl / tetrahydrofuran

5.1: 84 percent / PCC / CH₂Cl₂

6.1: 99 percent / NaOMe / 0 °C

7.1: 78 percent / iodoxybenzoic acid; p-TsOH / dimethylsulfoxide; toluene / 65 °C

8.1: 65 percent / NaBH₄-CeCl₃-7H₂O / -78 °C

With hydrogenchloride; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; copper(I) bromide dimethylsulfide complex; sodium methylate; toluene-4-sulfonic acid; pyridinium chlorochromate; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; toluene; 6.1: retro-Dickmann cleavage;
DOI:10.1055/s-2002-32603

Reference yield:

: 351033-77-7
(1S,5S,6S)-6-Methoxymethoxy-bicyclo[3.2.1]oct-3-en-2-one

: 467220-01-5
((1R,4S,6R)-6-Benzyloxymethyl-4-hydroxy-6-vinyl-cyclohex-2-enyl)-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 95 percent / BuLi / tetrahydrofuran / -78 °C

2.1: 75 percent / PCC / CH₂Cl₂

3.1: CuBr*Me₂S / tetrahydrofuran

3.2: HMPA; TMS-Cl / tetrahydrofuran / -78 °C

3.3: 92 percent / TBAF

4.1: 90 percent / aq. HCl / tetrahydrofuran

5.1: 84 percent / PCC / CH₂Cl₂

6.1: 99 percent / NaOMe / 0 °C

7.1: 78 percent / iodoxybenzoic acid; p-TsOH / dimethylsulfoxide; toluene / 65 °C

8.1: 65 percent / NaBH₄-CeCl₃-7H₂O / -78 °C

With hydrogenchloride; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; copper(I) bromide dimethylsulfide complex; sodium methylate; toluene-4-sulfonic acid; pyridinium chlorochromate; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; toluene; 6.1: retro-Dickmann cleavage;
DOI:10.1055/s-2002-32603