(3S,4S,5R)-8-(tert-butyldiphenylsiloxy)-3-(hydroxymethyl)-5-methyl-4-vinyloctanal dimethyl acetal

Base Information

Chemical Name:(3S,4S,5R)-8-(tert-butyldiphenylsiloxy)-3-(hydroxymethyl)-5-methyl-4-vinyloctanal dimethyl acetal
CAS No.:162789-35-7
Molecular Formula:C₃₀H₄₆O₄Si
Molecular Weight:498.778
Hs Code.:

Synonyms:(3S,4S,5R)-8-(tert-butyldiphenylsiloxy)-3-(hydroxymethyl)-5-methyl-4-vinyloctanal dimethyl acetal

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Chemical Property of (3S,4S,5R)-8-(tert-butyldiphenylsiloxy)-3-(hydroxymethyl)-5-methyl-4-vinyloctanal dimethyl acetal

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Technology Process of (3S,4S,5R)-8-(tert-butyldiphenylsiloxy)-3-(hydroxymethyl)-5-methyl-4-vinyloctanal dimethyl acetal

There total 18 articles about (3S,4S,5R)-8-(tert-butyldiphenylsiloxy)-3-(hydroxymethyl)-5-methyl-4-vinyloctanal dimethyl acetal 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: 80.0%

: (3S,4S)-3-[(R)-4-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-butyl]-4-(2,2-dimethoxy-ethyl)-tetrahydro-furan-2-ol

: 19493-09-5
Methylenetriphenylphosphorane

: 162789-35-7
(3S,4S,5R)-8-(tert-butyldiphenylsiloxy)-3-(hydroxymethyl)-5-methyl-4-vinyloctanal dimethyl acetal

Guidance literature:: DOI:10.1021/ja00109a041

Reference yield:

: 1117-61-9
(3R)-citronellol

: 162789-35-7
(3S,4S,5R)-8-(tert-butyldiphenylsiloxy)-3-(hydroxymethyl)-5-methyl-4-vinyloctanal dimethyl acetal

Guidance literature:: Multi-step reaction with 16 steps

1: 100 percent / pyridine, DMAP / CH₂Cl₂ / 0.75 h / 0 °C

2: 1.) O₃, 2.) BH₃*SMe₂ / 1.) CH₂Cl₂, -78 deg C, 2 h, 2.) CH₂Cl₂, 0 deg C, 3 h

3: 100 percent / DMAP, Et₃N / CH₂Cl₂ / Ambient temperature

4: 100 percent / aq. K₂CO₃ / methanol / 4 h / Heating

5: 17.5 g / pyridinium dichromate, 4A molecular sieves / CH₂Cl₂ / 1 h / Ambient temperature

6: NaClO₂, NaH₂PO₄*H₂O / 2-methyl-propan-2-ol; various solvent(s) / 6 h / Ambient temperature

7: 82 percent / diethyl ether / 1 h / Ambient temperature

8: 1.) LDA / 1.) THF, -78 deg C, 1 h, 2.) THF, -78 deg C, 30 min

9: 89 percent / diisopropylethylamine / CH₂Cl₂ / 12 h / Ambient temperature

10: 60 percent / 10percent aq. H₂SO₄ / tetrahydrofuran / 24 h

11: 44 percent / DBU / benzene / 9 h / 70 °C

12: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 3 min, 2.) THF, hexane, -78 deg C, 30 min

13: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, CH₃OH, -78 deg C, 2.) CH₂Cl₂, CH₃OH, from -78 deg C to RT, 1.5 h

14: 90 percent / p-TsOH*H₂O / methanol / 0.17 h

15: 97 percent / Dibal-H / CH₂Cl₂; hexane / 0.42 h / -78 °C

16: 1.) KN(SiMe₃)2 / 1.) THF, toluene, 30 min, 2.) THF, toluene, RT, 4.5 h

With pyridine; dmap; sodium chlorite; sodium dihydrogenphosphate; dipyridinium dichromate; n-butyllithium; dimethylsulfide; dimethylsulfide borane complex; 4 A molecular sieve; sulfuric acid; potassium hexamethylsilazane; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; tert-butyl alcohol; benzene;
DOI:10.1021/ja9533609

Reference yield:

: 20425-54-1,67650-82-2
(R)-1-citronellyl acetate

: 162789-35-7
(3S,4S,5R)-8-(tert-butyldiphenylsiloxy)-3-(hydroxymethyl)-5-methyl-4-vinyloctanal dimethyl acetal

Guidance literature:: Multi-step reaction with 15 steps

1: 1.) O₃, 2.) BH₃*SMe₂ / 1.) CH₂Cl₂, -78 deg C, 2 h, 2.) CH₂Cl₂, 0 deg C, 3 h

2: 100 percent / DMAP, Et₃N / CH₂Cl₂ / Ambient temperature

3: 100 percent / aq. K₂CO₃ / methanol / 4 h / Heating

4: 17.5 g / pyridinium dichromate, 4A molecular sieves / CH₂Cl₂ / 1 h / Ambient temperature

5: NaClO₂, NaH₂PO₄*H₂O / 2-methyl-propan-2-ol; various solvent(s) / 6 h / Ambient temperature

6: 82 percent / diethyl ether / 1 h / Ambient temperature

7: 1.) LDA / 1.) THF, -78 deg C, 1 h, 2.) THF, -78 deg C, 30 min

8: 89 percent / diisopropylethylamine / CH₂Cl₂ / 12 h / Ambient temperature

9: 60 percent / 10percent aq. H₂SO₄ / tetrahydrofuran / 24 h

10: 44 percent / DBU / benzene / 9 h / 70 °C

11: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 3 min, 2.) THF, hexane, -78 deg C, 30 min

12: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, CH₃OH, -78 deg C, 2.) CH₂Cl₂, CH₃OH, from -78 deg C to RT, 1.5 h

13: 90 percent / p-TsOH*H₂O / methanol / 0.17 h

14: 97 percent / Dibal-H / CH₂Cl₂; hexane / 0.42 h / -78 °C

15: 1.) KN(SiMe₃)2 / 1.) THF, toluene, 30 min, 2.) THF, toluene, RT, 4.5 h

With dmap; sodium chlorite; sodium dihydrogenphosphate; dipyridinium dichromate; n-butyllithium; dimethylsulfide; dimethylsulfide borane complex; 4 A molecular sieve; sulfuric acid; potassium hexamethylsilazane; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; tert-butyl alcohol; benzene;
DOI:10.1021/ja9533609