(2S,3S,5S,6R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-((1S,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-2,6-dimethyl-heptanal

Base Information

Chemical Name:(2S,3S,5S,6R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-((1S,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-2,6-dimethyl-heptanal
CAS No.:135708-92-8
Molecular Formula:C₂₈H₅₈O₅Si₂
Molecular Weight:530.937
Hs Code.:

Synonyms:(2S,3S,5S,6R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-((1S,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-2,6-dimethyl-heptanal

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Chemical Property of (2S,3S,5S,6R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-((1S,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-2,6-dimethyl-heptanal

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Technology Process of (2S,3S,5S,6R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-((1S,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-2,6-dimethyl-heptanal

There total 18 articles about (2S,3S,5S,6R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-((1S,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-2,6-dimethyl-heptanal 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: 73.0%

: 135708-91-7
(1R,2R,4S)-4-[(2R,3S,5S,6R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-2,6-dimethyl-heptyl]-2-methoxy-cyclohexanol

: 135708-92-8
(2S,3S,5S,6R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-((1S,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-2,6-dimethyl-heptanal

Guidance literature:: With tris(triphenylphosphine)ruthenium(II) chloride; In benzene; for 18h; Ambient temperature;
DOI:10.1021/jo00020a026

Reference yield:

: 89046-67-3,91796-47-3,91796-48-4,91798-02-6,91798-03-7,94233-73-5,94233-74-6,106357-32-8
(5R)-6-benzyloxy-5-methyl-4-hydroxyhex-1-ene

: 135708-92-8
(2S,3S,5S,6R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-((1S,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-2,6-dimethyl-heptanal

Guidance literature:: Multi-step reaction with 17 steps

1: 98 percent / imidazole / dimethylformamide / 48 h / Ambient temperature

2: 1) O₃, pyridine, 2) DMS / 1) MeOH, CH₂Cl₂, -78 deg C, 2) r.t., 15 h

3: 2) 15percent aq.NaOH / 1) toluene, -78 deg C, 2 h, 2) r.t., 16 h

4: Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

5: 93 percent / imidazole / dimethylformamide / 20 h / Ambient temperature

6: 1) 9-BBN, 2) 30percent H₂O₂, 3M NaOH / 1) THF, r.t., 4 h, 2) 0 deg C, 1 h

7: 90 percent / oxalyl chloride, DMSO, Et₃N / CH₂Cl₂

8: 99 percent / KMnO₄, NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O

9: 75 percent / 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide (EDCI), 4-(dimethylamino)pyridine (DMAP) / CH₂Cl₂ / 16 h / Ambient temperature

10: 1) LDA, HMPA / 1) THF, hexane, -78 deg C, 15 min, 2) THF, r.t., 0.5 h

11: toluene / 2 h / Heating

12: 0.1N aq.LiOH / tetrahydrofuran / 2 h

13: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide (EDCI), 4-(dimethylamino)pyridine (DMAP) / CH₂Cl₂ / 8 h

14: N-methylcarbazole, t-BuSH / aq. propan-2-ol / 2 h / Irradiation

15: 2) H₂ / 1) Raney-Ni, 2) PtO₂ / 1) EtOH, 30 min, 2) EtOAc, 45 min

16: H₂ / 10percent Pd-C / ethyl acetate / 6 h

17: 73 percent / RuCl₂(PPh₃)3 / benzene / 18 h / Ambient temperature

With pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium hydroxide; sodium hydroxide; potassium permanganate; sodium dihydrogenphosphate; 9-borabicyclo[3.3.1]nonane dimer; tris(triphenylphosphine)ruthenium(II) chloride; N-methylcarbazole; oxalyl dichloride; 2,3-dimercapto-succinic acid; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; ozone; 2-methylpropan-2-thiol; dimethyl sulfoxide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; lithium diisopropyl amide; platinum(IV) oxide; palladium on activated charcoal; nickel; In tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol; toluene; tert-butyl alcohol; benzene;
DOI:10.1021/jo00020a026

Reference yield:

: 135708-75-7,135708-76-8
[1-((R)-2-Benzyloxy-1-methyl-ethyl)-but-3-enyloxy]-tert-butyl-dimethyl-silane

: 135708-92-8
(2S,3S,5S,6R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-((1S,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-2,6-dimethyl-heptanal

Guidance literature:: Multi-step reaction with 16 steps

1: 1) O₃, pyridine, 2) DMS / 1) MeOH, CH₂Cl₂, -78 deg C, 2) r.t., 15 h

2: 2) 15percent aq.NaOH / 1) toluene, -78 deg C, 2 h, 2) r.t., 16 h

3: Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

4: 93 percent / imidazole / dimethylformamide / 20 h / Ambient temperature

5: 1) 9-BBN, 2) 30percent H₂O₂, 3M NaOH / 1) THF, r.t., 4 h, 2) 0 deg C, 1 h

6: 90 percent / oxalyl chloride, DMSO, Et₃N / CH₂Cl₂

7: 99 percent / KMnO₄, NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O

8: 75 percent / 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide (EDCI), 4-(dimethylamino)pyridine (DMAP) / CH₂Cl₂ / 16 h / Ambient temperature

9: 1) LDA, HMPA / 1) THF, hexane, -78 deg C, 15 min, 2) THF, r.t., 0.5 h

10: toluene / 2 h / Heating

11: 0.1N aq.LiOH / tetrahydrofuran / 2 h

12: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide (EDCI), 4-(dimethylamino)pyridine (DMAP) / CH₂Cl₂ / 8 h

13: N-methylcarbazole, t-BuSH / aq. propan-2-ol / 2 h / Irradiation

14: 2) H₂ / 1) Raney-Ni, 2) PtO₂ / 1) EtOH, 30 min, 2) EtOAc, 45 min

15: H₂ / 10percent Pd-C / ethyl acetate / 6 h

16: 73 percent / RuCl₂(PPh₃)3 / benzene / 18 h / Ambient temperature

With pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium hydroxide; sodium hydroxide; potassium permanganate; sodium dihydrogenphosphate; 9-borabicyclo[3.3.1]nonane dimer; tris(triphenylphosphine)ruthenium(II) chloride; N-methylcarbazole; oxalyl dichloride; 2,3-dimercapto-succinic acid; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; ozone; 2-methylpropan-2-thiol; dimethyl sulfoxide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; lithium diisopropyl amide; platinum(IV) oxide; palladium on activated charcoal; nickel; In tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol; toluene; tert-butyl alcohol; benzene;
DOI:10.1021/jo00020a026