(1S,3R,4S,5R)-1-[(3E,5R)-3,5-dimethyl-6-phenyl-3-hexenyl]-4-hydroxy-3-hydroxymethyl-4,5-bis(methoxycarbonyl)-2,8-dioxabicyclo[3.2.1]octane

Base Information

Chemical Name:(1S,3R,4S,5R)-1-[(3E,5R)-3,5-dimethyl-6-phenyl-3-hexenyl]-4-hydroxy-3-hydroxymethyl-4,5-bis(methoxycarbonyl)-2,8-dioxabicyclo[3.2.1]octane
CAS No.:215173-36-7
Molecular Formula:C₂₅H₃₄O₈
Molecular Weight:462.54
Hs Code.:

Synonyms:(1S,3R,4S,5R)-1-[(3E,5R)-3,5-dimethyl-6-phenyl-3-hexenyl]-4-hydroxy-3-hydroxymethyl-4,5-bis(methoxycarbonyl)-2,8-dioxabicyclo[3.2.1]octane

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Chemical Property of (1S,3R,4S,5R)-1-[(3E,5R)-3,5-dimethyl-6-phenyl-3-hexenyl]-4-hydroxy-3-hydroxymethyl-4,5-bis(methoxycarbonyl)-2,8-dioxabicyclo[3.2.1]octane

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Technology Process of (1S,3R,4S,5R)-1-[(3E,5R)-3,5-dimethyl-6-phenyl-3-hexenyl]-4-hydroxy-3-hydroxymethyl-4,5-bis(methoxycarbonyl)-2,8-dioxabicyclo[3.2.1]octane

There total 21 articles about (1S,3R,4S,5R)-1-[(3E,5R)-3,5-dimethyl-6-phenyl-3-hexenyl]-4-hydroxy-3-hydroxymethyl-4,5-bis(methoxycarbonyl)-2,8-dioxabicyclo[3.2.1]octane 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%

: 67-56-1
methanol

: (5R,8R,9S)-8-(tert-Butyl-diphenyl-silanyloxymethyl)-2-((E)-(R)-3,5-dimethyl-6-phenyl-hex-3-enyl)-2-hydroxy-6-oxo-9-trimethylsilanyloxy-1,7-dioxa-spiro[4.4]nonane-9-carboxylic acid methyl ester

: 215173-36-7
(1S,3R,4S,5R)-1-[(3E,5R)-3,5-dimethyl-6-phenyl-3-hexenyl]-4-hydroxy-3-hydroxymethyl-4,5-bis(methoxycarbonyl)-2,8-dioxabicyclo[3.2.1]octane

: (5R,8R,9S)-2-[(3E,5R)-3,5-dimethyl-6-phenyl-3-hexenyl]-9-hydroxy-8-(hydroxymethyl)-2-methoxy-9-methoxycarbonyl-1,7-dioxaspiro[4.4]nonan-6-one

Guidance literature:: With sulfuric acid;
DOI:10.1021/jo981684k

Reference yield:

: 215173-30-1
methyl (3R)-4-tert-butyldiphenylsiloxy-3-(5-phenylthio-2-furoyloxy)-2-oxobutanoate

: 215173-36-7
(1S,3R,4S,5R)-1-[(3E,5R)-3,5-dimethyl-6-phenyl-3-hexenyl]-4-hydroxy-3-hydroxymethyl-4,5-bis(methoxycarbonyl)-2,8-dioxabicyclo[3.2.1]octane

Guidance literature:: Multi-step reaction with 3 steps

1.1: 89 percent / H₂ / Pd/C / ethyl acetate / 15 h / 20 °C

2.1: n-BuLi / hexane; tetrahydrofuran / 2 h / -78 - 0 °C

2.2: Al(Hg) / hexamethylphosphoric acid triamide; tetrahydrofuran; H₂O / 3 h / 20 °C

2.3: 7.6 mg / aq. H₂SO₄ / methanol / 40 h / 20 °C

With n-butyllithium; hydrogen; palladium on activated charcoal; In tetrahydrofuran; hexane; ethyl acetate;
DOI:10.1021/jo011157s

Reference yield:

: 215173-29-8
methyl (2S,3R)-4-tert-butyldiphenylsiloxy-3-(5-phenylthio-2-furoyloxy)-2-(tetrahydro-2H-pyran-2-yloxy)butanoate

: 215173-36-7
(1S,3R,4S,5R)-1-[(3E,5R)-3,5-dimethyl-6-phenyl-3-hexenyl]-4-hydroxy-3-hydroxymethyl-4,5-bis(methoxycarbonyl)-2,8-dioxabicyclo[3.2.1]octane

Guidance literature:: Multi-step reaction with 5 steps

1.1: 95 percent / Me₂AlCl / CH₂Cl₂; various solvent(s) / 4 h / -25 - 20 °C

2.1: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.25 h / 20 °C

3.1: 89 percent / H₂ / Pd/C / ethyl acetate / 15 h / 20 °C

4.1: n-BuLi / hexane; tetrahydrofuran / 2 h / -78 - 0 °C

4.2: Al(Hg) / hexamethylphosphoric acid triamide; tetrahydrofuran; H₂O / 3 h / 20 °C

4.3: 7.6 mg / aq. H₂SO₄ / methanol / 40 h / 20 °C

With n-butyllithium; hydrogen; dimethylaluminum chloride; Dess-Martin periodane; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate; 2.1: Dess-Martin oxidation;
DOI:10.1021/jo011157s