(3S,4S)-4-<(1R)-4-(tert-butyldiphenylsiloxy)-1-methylbutyl>tetrahydro-5-oxo-3-furanacetaldehyde

Base Information

Chemical Name:(3S,4S)-4-<(1R)-4-(tert-butyldiphenylsiloxy)-1-methylbutyl>tetrahydro-5-oxo-3-furanacetaldehyde
CAS No.:168788-45-2
Molecular Formula:C₂₇H₃₆O₄Si
Molecular Weight:452.666
Hs Code.:

Synonyms:(3S,4S)-4-<(1R)-4-(tert-butyldiphenylsiloxy)-1-methylbutyl>tetrahydro-5-oxo-3-furanacetaldehyde

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Chemical Property of (3S,4S)-4-<(1R)-4-(tert-butyldiphenylsiloxy)-1-methylbutyl>tetrahydro-5-oxo-3-furanacetaldehyde

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Technology Process of (3S,4S)-4-<(1R)-4-(tert-butyldiphenylsiloxy)-1-methylbutyl>tetrahydro-5-oxo-3-furanacetaldehyde

There total 15 articles about (3S,4S)-4-<(1R)-4-(tert-butyldiphenylsiloxy)-1-methylbutyl>tetrahydro-5-oxo-3-furanacetaldehyde 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: 79.0%

: 162789-33-5
(3S,4S)-3-<(1R)-4-(tert-butyldiphenylsiloxy)-1-methylbutyl>dihydro-4-<(E)-3-(octahydro-1,3-dimethyl-2H-1,3,2-benzodiazaphosphol-2-yl)allyl>-2(3H)furanone

: 168788-45-2
(3S,4S)-4-<(1R)-4-(tert-butyldiphenylsiloxy)-1-methylbutyl>tetrahydro-5-oxo-3-furanacetaldehyde

Guidance literature:: With dimethylsulfide; ozone;
DOI:10.1021/ja00109a041

Reference yield:

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

: 168788-45-2
(3S,4S)-4-<(1R)-4-(tert-butyldiphenylsiloxy)-1-methylbutyl>tetrahydro-5-oxo-3-furanacetaldehyde

Guidance literature:: Multi-step reaction with 12 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

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

Reference yield:

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

: 168788-45-2
(3S,4S)-4-<(1R)-4-(tert-butyldiphenylsiloxy)-1-methylbutyl>tetrahydro-5-oxo-3-furanacetaldehyde

Guidance literature:: Multi-step reaction with 13 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

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