(E)-(4R,5R)-8-Triisopropylsilanyloxy-5-(2-trityloxy-ethyl)-octa-1,6-diene-4,5-diol

Base Information

Chemical Name:(E)-(4R,5R)-8-Triisopropylsilanyloxy-5-(2-trityloxy-ethyl)-octa-1,6-diene-4,5-diol
CAS No.:521274-24-8
Molecular Formula:C₃₈H₅₂O₄Si
Molecular Weight:600.914
Hs Code.:

Synonyms:(E)-(4R,5R)-8-Triisopropylsilanyloxy-5-(2-trityloxy-ethyl)-octa-1,6-diene-4,5-diol

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Chemical Property of (E)-(4R,5R)-8-Triisopropylsilanyloxy-5-(2-trityloxy-ethyl)-octa-1,6-diene-4,5-diol

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Technology Process of (E)-(4R,5R)-8-Triisopropylsilanyloxy-5-(2-trityloxy-ethyl)-octa-1,6-diene-4,5-diol

There total 11 articles about (E)-(4R,5R)-8-Triisopropylsilanyloxy-5-(2-trityloxy-ethyl)-octa-1,6-diene-4,5-diol 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:

: 521274-19-1
(4-hydroxymethyl-2,2-dimethyl-[1,3]-dioxan-4-yl)-methanol

: 521274-24-8
(E)-(4R,5R)-8-Triisopropylsilanyloxy-5-(2-trityloxy-ethyl)-octa-1,6-diene-4,5-diol

Guidance literature:: Multi-step reaction with 11 steps

1.1: lipase AK / hexane; H₂O / 17 h / 20 °C

1.2: imidazole / dimethylformamide / 1.5 h / 20 °C

2.1: K₂CO₃; MeOH / 2.5 h / 20 °C

3.1: TPAP; NMO; 4 A molecular sieves / CH₂Cl₂ / 1.17 h / 20 °C

4.1: toluene / 11 h / 100 °C

5.1: DIBAL / CH₂Cl₂; toluene / 0.17 h / -78 °C

6.1: TBAF / tetrahydrofuran / 20 °C

7.1: imidazole / CH₂Cl₂ / 2 h / 0 °C

8.1: TPAP; NMO; 4 A molecular sieves / CH₂Cl₂ / 3 h / 20 °C

9.1: 8.12 g / diethyl ether / -78 °C

10.1: PPTS / methanol / 0.67 h / 20 °C

11.1: pyridine; DMAP / 6 h / 50 °C

With pyridine; 1H-imidazole; methanol; dmap; N-methyl-2-indolinone; tetrapropylammonium perruthennate; lipase AK; 4 A molecular sieve; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; toluene; 4.1: Wittig reaction;
DOI:10.1021/ja0340679

Reference yield:

: (E)-3-((R)-4-Hydroxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-propenol

: 521274-24-8
(E)-(4R,5R)-8-Triisopropylsilanyloxy-5-(2-trityloxy-ethyl)-octa-1,6-diene-4,5-diol

Guidance literature:: Multi-step reaction with 5 steps

1: imidazole / CH₂Cl₂ / 2 h / 0 °C

2: TPAP; NMO; 4 A molecular sieves / CH₂Cl₂ / 3 h / 20 °C

3: 8.12 g / diethyl ether / -78 °C

4: PPTS / methanol / 0.67 h / 20 °C

5: pyridine; DMAP / 6 h / 50 °C

With pyridine; 1H-imidazole; dmap; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; pyridinium p-toluenesulfonate; In methanol; diethyl ether; dichloromethane;
DOI:10.1021/ja0340679

Reference yield:

: 4-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxane-4-carbaldehyde

: 521274-24-8
(E)-(4R,5R)-8-Triisopropylsilanyloxy-5-(2-trityloxy-ethyl)-octa-1,6-diene-4,5-diol

Guidance literature:: Multi-step reaction with 8 steps

1: toluene / 11 h / 100 °C

2: DIBAL / CH₂Cl₂; toluene / 0.17 h / -78 °C

3: TBAF / tetrahydrofuran / 20 °C

4: imidazole / CH₂Cl₂ / 2 h / 0 °C

5: TPAP; NMO; 4 A molecular sieves / CH₂Cl₂ / 3 h / 20 °C

6: 8.12 g / diethyl ether / -78 °C

7: PPTS / methanol / 0.67 h / 20 °C

8: pyridine; DMAP / 6 h / 50 °C

With pyridine; 1H-imidazole; dmap; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; 1: Wittig reaction;
DOI:10.1021/ja0340679