(S)-3-((S)-5-benzyloxy-3-methyl-pentyl)-6-(tert-butyl-dimethyl-silanyloxy)-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalene-1,2-dicarboxylic acid

Base Information

Chemical Name:(S)-3-((S)-5-benzyloxy-3-methyl-pentyl)-6-(tert-butyl-dimethyl-silanyloxy)-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalene-1,2-dicarboxylic acid
CAS No.:1312554-83-8
Molecular Formula:C₃₅H₅₂O₆Si
Molecular Weight:596.88
Hs Code.:

Synonyms:(S)-3-((S)-5-benzyloxy-3-methyl-pentyl)-6-(tert-butyl-dimethyl-silanyloxy)-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalene-1,2-dicarboxylic acid

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Chemical Property of (S)-3-((S)-5-benzyloxy-3-methyl-pentyl)-6-(tert-butyl-dimethyl-silanyloxy)-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalene-1,2-dicarboxylic acid

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Technology Process of (S)-3-((S)-5-benzyloxy-3-methyl-pentyl)-6-(tert-butyl-dimethyl-silanyloxy)-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalene-1,2-dicarboxylic acid

There total 7 articles about (S)-3-((S)-5-benzyloxy-3-methyl-pentyl)-6-(tert-butyl-dimethyl-silanyloxy)-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalene-1,2-dicarboxylic acid 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: 59.0%

: [(S)-3-((S)-7-benzyloxy-5-methyl-hept-1-enyl)-2,2-dimethyl-cyclohex-3-enyloxy]-tert-butyl-dimethyl-silane

: 762-42-5
dimethyl acetylenedicarboxylate

: 1312554-83-8
(S)-3-((S)-5-benzyloxy-3-methyl-pentyl)-6-(tert-butyl-dimethyl-silanyloxy)-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalene-1,2-dicarboxylic acid

Guidance literature:: [(S)-3-((S)-7-benzyloxy-5-methyl-hept-1-enyl)-2,2-dimethyl-cyclohex-3-enyloxy]-tert-butyl-dimethyl-silane; dimethyl acetylenedicarboxylate; at 110 ℃; for 18h; Inert atmosphere;

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In benzene; at 20 ℃; for 12h; Inert atmosphere;
DOI:10.1021/ol201336x

Reference yield: 42.0%

: 1312554-75-8
tert-butyl-[(S)-1-(1,1-dimethyl-prop-2-ynyl)-pent-4-enyloxy]-dimethyl-silane

: 762-42-5
dimethyl acetylenedicarboxylate

: 175170-59-9
((S)-3-methyl-hept-6-enyloxymethyl)-benzene

: 1312554-83-8
(S)-3-((S)-5-benzyloxy-3-methyl-pentyl)-6-(tert-butyl-dimethyl-silanyloxy)-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalene-1,2-dicarboxylic acid

Guidance literature:: tert-butyl-[(S)-1-(1,1-dimethyl-prop-2-ynyl)-pent-4-enyloxy]-dimethyl-silane; ((S)-3-methyl-hept-6-enyloxymethyl)-benzene; With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In toluene; at 50 ℃; for 18h; Inert atmosphere;

dimethyl acetylenedicarboxylate; In toluene; at 110 ℃; for 10h; Inert atmosphere;

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In toluene; Inert atmosphere;
DOI:10.1021/ol201336x

Reference yield:

: 1312554-79-2
tert-butyl-{(S)-1-[2-(4-methoxy-benzyloxy)-1,1-dimethyl-ethyl]-pent-4-enyloxy}-dimethyl-silane

: 1312554-83-8
(S)-3-((S)-5-benzyloxy-3-methyl-pentyl)-6-(tert-butyl-dimethyl-silanyloxy)-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalene-1,2-dicarboxylic acid

Guidance literature:: Multi-step reaction with 4 steps

1.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h / 0 °C / pH 7 / Inert atmosphere; aq. buffer

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

2.2: -78 - 0 °C / Inert atmosphere

3.1: potassium carbonate / methanol / 16 h / 20 °C / Inert atmosphere

4.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 18 h / 50 °C / Inert atmosphere

4.2: 10 h / 110 °C / Inert atmosphere

4.3: Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; oxalyl dichloride; potassium carbonate; dimethyl sulfoxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; dichloromethane; toluene; 2.1: Swern oxidation / 2.2: Swern oxidation;
DOI:10.1021/ol201336x