(S)-2-[(2R,5S)-5-((R)-3-Benzenesulfonyl-1-hydroxy-propyl)-5-methyl-tetrahydro-furan-2-yl]-6-methyl-hept-5-en-2-ol

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Chemical Name:(S)-2-[(2R,5S)-5-((R)-3-Benzenesulfonyl-1-hydroxy-propyl)-5-methyl-tetrahydro-furan-2-yl]-6-methyl-hept-5-en-2-ol
CAS No.:678999-17-2
Molecular Formula:C₂₂H₃₄O₅S
Molecular Weight:410.575
Hs Code.:

Synonyms:(S)-2-[(2R,5S)-5-((R)-3-Benzenesulfonyl-1-hydroxy-propyl)-5-methyl-tetrahydro-furan-2-yl]-6-methyl-hept-5-en-2-ol

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Chemical Property of (S)-2-[(2R,5S)-5-((R)-3-Benzenesulfonyl-1-hydroxy-propyl)-5-methyl-tetrahydro-furan-2-yl]-6-methyl-hept-5-en-2-ol

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Technology Process of (S)-2-[(2R,5S)-5-((R)-3-Benzenesulfonyl-1-hydroxy-propyl)-5-methyl-tetrahydro-furan-2-yl]-6-methyl-hept-5-en-2-ol

There total 11 articles about (S)-2-[(2R,5S)-5-((R)-3-Benzenesulfonyl-1-hydroxy-propyl)-5-methyl-tetrahydro-furan-2-yl]-6-methyl-hept-5-en-2-ol 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%

: 3112-85-4
methylphenylsulfonate

: 678999-05-8
(S)-6-Methyl-2-((2R,5S)-5-methyl-5-(R)-oxiranyl-tetrahydro-furan-2-yl)-hept-5-en-2-ol

: 678999-17-2
(S)-2-[(2R,5S)-5-((R)-3-Benzenesulfonyl-1-hydroxy-propyl)-5-methyl-tetrahydro-furan-2-yl]-6-methyl-hept-5-en-2-ol

Guidance literature:: With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium; In tetrahydrofuran; hexane; at -78 - -25 ℃; for 5h;
DOI:10.1021/ol036471i

Reference yield:

: 35189-96-9
3-methyl-2-butenylmagnesium chloride

: 678999-17-2
(S)-2-[(2R,5S)-5-((R)-3-Benzenesulfonyl-1-hydroxy-propyl)-5-methyl-tetrahydro-furan-2-yl]-6-methyl-hept-5-en-2-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 70 percent / CuI / tetrahydrofuran / 0.5 h / -15 °C

2: 87 percent / aq. p-TsOH / ethanol / 2 h / 50 °C

3: 82 percent / pyridine / 1 h / 0 °C

4: 92 percent / K₂CO₃ / methanol / 0.33 h / 0 °C

5: 100 percent / n-BuLi; DMPU / tetrahydrofuran; hexane / 5 h / -78 - -25 °C

With pyridine; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; copper(l) iodide; n-butyllithium; potassium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; ethanol; hexane;
DOI:10.1021/ol036471i

Reference yield:

: 158512-40-4
(E)-(R)-8-(tert-Butyl-dimethyl-silanyloxy)-2,6-dimethyl-octa-1,6-dien-3-ol

: 678999-17-2
(S)-2-[(2R,5S)-5-((R)-3-Benzenesulfonyl-1-hydroxy-propyl)-5-methyl-tetrahydro-furan-2-yl]-6-methyl-hept-5-en-2-ol

Guidance literature:: Multi-step reaction with 10 steps

1: 90 percent / VO(acac)2; TBHP / benzene; H₂O / 0.33 h / 20 °C

2: m-CPBA / CH₂Cl₂ / 3 h / 0 °C

3: 5.100 g / silica gel / 48 h

4: 100 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C

5: 91 percent / PPTS / CH₂Cl₂ / 7 h / 20 °C

6: 70 percent / CuI / tetrahydrofuran / 0.5 h / -15 °C

7: 87 percent / aq. p-TsOH / ethanol / 2 h / 50 °C

8: 82 percent / pyridine / 1 h / 0 °C

9: 92 percent / K₂CO₃ / methanol / 0.33 h / 0 °C

10: 100 percent / n-BuLi; DMPU / tetrahydrofuran; hexane / 5 h / -78 - -25 °C

With pyridine; tert.-butylhydroperoxide; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; copper(l) iodide; n-butyllithium; bis(acetylacetonate)oxovanadium; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; silica gel; potassium carbonate; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; benzene;
DOI:10.1021/ol036471i