7-(3,4-dihydroxy-1-methyl-4-phenyl-1-triethylsilanyloxy-butyl)-3-methyl-5-methylene-oct-7-enenitrile

Base Information

Chemical Name:7-(3,4-dihydroxy-1-methyl-4-phenyl-1-triethylsilanyloxy-butyl)-3-methyl-5-methylene-oct-7-enenitrile
CAS No.:866148-39-2
Molecular Formula:C₂₇H₄₃NO₃Si
Molecular Weight:457.729
Hs Code.:

Synonyms:7-(3,4-dihydroxy-1-methyl-4-phenyl-1-triethylsilanyloxy-butyl)-3-methyl-5-methylene-oct-7-enenitrile

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Chemical Property of 7-(3,4-dihydroxy-1-methyl-4-phenyl-1-triethylsilanyloxy-butyl)-3-methyl-5-methylene-oct-7-enenitrile

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Technology Process of 7-(3,4-dihydroxy-1-methyl-4-phenyl-1-triethylsilanyloxy-butyl)-3-methyl-5-methylene-oct-7-enenitrile

There total 20 articles about 7-(3,4-dihydroxy-1-methyl-4-phenyl-1-triethylsilanyloxy-butyl)-3-methyl-5-methylene-oct-7-enenitrile 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: 90.0%

: C₂₇H₄₁NOSi

: 866148-39-2
7-(3,4-dihydroxy-1-methyl-4-phenyl-1-triethylsilanyloxy-butyl)-3-methyl-5-methylene-oct-7-enenitrile

Guidance literature:: With methanesulfonamide; AD-mix-β*; In water; tert-butyl alcohol; for 16h; Optical yield = 13.043 %de; regioselective reaction;
DOI:10.1021/jo3026077

Reference yield:

: 866148-30-3
(R)-4-Methyl-5-triisopropylsilanyloxy-2-trimethylsilanylmethyl-pent-1-ene

: 866148-39-2
7-(3,4-dihydroxy-1-methyl-4-phenyl-1-triethylsilanyloxy-butyl)-3-methyl-5-methylene-oct-7-enenitrile

Guidance literature:: Multi-step reaction with 5 steps

1.1: 65 percent / TiCl₄ / CH₂Cl₂ / 0.25 h / -78 °C

2.1: SOCl₂; pyridine / toluene / 0.5 h / -78 °C

2.2: TBAF / tetrahydrofuran / 0 - 20 °C

3.1: 81 percent / PPh₃; DEAD / diethyl ether; toluene / 0 - 20 °C

4.1: 77 percent / Et₃N / CH₂Cl₂ / -78 - 20 °C

5.1: MeSO₂NH₂; (DHQD)2PHAL; K₂OsO₄*2H₂O / K₂CO₃; K₃Fe(CN)6 / H₂O; 2-methyl-propan-2-ol / 16 h

With pyridine; potassium osmate(VI); thionyl chloride; methanesulfonamide; titanium tetrachloride; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; triphenylphosphine; diethylazodicarboxylate; potassium carbonate; potassium hexacyanoferrate(III); In diethyl ether; dichloromethane; water; toluene; tert-butyl alcohol; 3.1: Mitsunobu reaction / 5.1: Sharpless dihydroxylation;
DOI:10.1021/ol051544e

Reference yield:

: 866148-29-0
(S)-4-Benzyl-3-((R)-2-methyl-4-trimethylsilanylmethyl-pent-4-enoyl)-oxazolidin-2-one

: 866148-39-2
7-(3,4-dihydroxy-1-methyl-4-phenyl-1-triethylsilanyloxy-butyl)-3-methyl-5-methylene-oct-7-enenitrile

Guidance literature:: Multi-step reaction with 7 steps

1.1: 99 percent / LiBH₄ / methanol; tetrahydrofuran / 0 - 20 °C

2.1: 99 percent / Et₃N / CH₂Cl₂ / -78 - 20 °C

3.1: 65 percent / TiCl₄ / CH₂Cl₂ / 0.25 h / -78 °C

4.1: SOCl₂; pyridine / toluene / 0.5 h / -78 °C

4.2: TBAF / tetrahydrofuran / 0 - 20 °C

5.1: 81 percent / PPh₃; DEAD / diethyl ether; toluene / 0 - 20 °C

6.1: 77 percent / Et₃N / CH₂Cl₂ / -78 - 20 °C

7.1: MeSO₂NH₂; (DHQD)2PHAL; K₂OsO₄*2H₂O / K₂CO₃; K₃Fe(CN)6 / H₂O; 2-methyl-propan-2-ol / 16 h

With pyridine; potassium osmate(VI); lithium borohydride; thionyl chloride; methanesulfonamide; titanium tetrachloride; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; triphenylphosphine; diethylazodicarboxylate; potassium carbonate; potassium hexacyanoferrate(III); In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene; tert-butyl alcohol; 5.1: Mitsunobu reaction / 7.1: Sharpless dihydroxylation;
DOI:10.1021/ol051544e