Trifluoro-acetic acid (1S,4R,5R)-5-benzyloxymethyl-4-methoxycarbonylmethyl-5-vinyl-cyclohex-2-enyl ester

Base Information

Chemical Name:Trifluoro-acetic acid (1S,4R,5R)-5-benzyloxymethyl-4-methoxycarbonylmethyl-5-vinyl-cyclohex-2-enyl ester
CAS No.:467220-03-7
Molecular Formula:C₂₁H₂₃F₃O₅
Molecular Weight:412.406
Hs Code.:

Synonyms:Trifluoro-acetic acid (1S,4R,5R)-5-benzyloxymethyl-4-methoxycarbonylmethyl-5-vinyl-cyclohex-2-enyl ester

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Chemical Property of Trifluoro-acetic acid (1S,4R,5R)-5-benzyloxymethyl-4-methoxycarbonylmethyl-5-vinyl-cyclohex-2-enyl ester

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Technology Process of Trifluoro-acetic acid (1S,4R,5R)-5-benzyloxymethyl-4-methoxycarbonylmethyl-5-vinyl-cyclohex-2-enyl ester

There total 10 articles about Trifluoro-acetic acid (1S,4R,5R)-5-benzyloxymethyl-4-methoxycarbonylmethyl-5-vinyl-cyclohex-2-enyl 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: 100.0%

: 407-25-0
trifluoroacetic anhydride

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

: 467220-03-7
Trifluoro-acetic acid (1S,4R,5R)-5-benzyloxymethyl-4-methoxycarbonylmethyl-5-vinyl-cyclohex-2-enyl ester

Guidance literature:: With pyridine; In tetrahydrofuran;
DOI:10.1055/s-2002-32603

Reference yield:

: 66222-28-4
(benzyloxymethyl)tributylstannane

: 467220-03-7
Trifluoro-acetic acid (1S,4R,5R)-5-benzyloxymethyl-4-methoxycarbonylmethyl-5-vinyl-cyclohex-2-enyl ester

Guidance literature:: Multi-step reaction with 9 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

9.1: 100 percent / pyridine / tetrahydrofuran

With pyridine; 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

: 467220-03-7
Trifluoro-acetic acid (1S,4R,5R)-5-benzyloxymethyl-4-methoxycarbonylmethyl-5-vinyl-cyclohex-2-enyl ester

Guidance literature:: Multi-step reaction with 9 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

9.1: 100 percent / pyridine / tetrahydrofuran

With pyridine; 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