(E)-(R)-1-[(4S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-penta-2,4-dien-1-ol

Base Information

Chemical Name:(E)-(R)-1-[(4S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-penta-2,4-dien-1-ol
CAS No.:596092-40-9
Molecular Formula:C₂₇H₃₆O₄Si
Molecular Weight:452.666
Hs Code.:

Synonyms:(E)-(R)-1-[(4S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-penta-2,4-dien-1-ol

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Chemical Property of (E)-(R)-1-[(4S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-penta-2,4-dien-1-ol

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Technology Process of (E)-(R)-1-[(4S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-penta-2,4-dien-1-ol

There total 2 articles about (E)-(R)-1-[(4S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-penta-2,4-dien-1-ol 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: 53.0%

: 78845-12-2,81925-31-7
(E)-1-tri-n-butylstannyl-1,3-butadiene

: 101331-92-4
4-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-L-threose

: 596092-40-9
(E)-(R)-1-[(4S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-penta-2,4-dien-1-ol

: 596092-39-6
(E)-(S)-1-[(4S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-penta-2,4-dien-1-ol

Guidance literature:: (E)-1-tri-n-butylstannyl-1,3-butadiene; With n-butyllithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; at -78 ℃; for 1h;

4-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-L-threose; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; at -78 ℃; for 2h;
DOI:10.1021/ol034823f

Reference yield:

: 136032-73-0,127251-09-6
4-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-L-threitol

: 596092-40-9
(E)-(R)-1-[(4S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-penta-2,4-dien-1-ol

Guidance literature:: Multi-step reaction with 2 steps

1.1: 91 percent / oxalyl chloride; DMSO / CH₂Cl₂ / 0.58 h / -78 °C

2.1: n-BuLi / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 1 h / -78 °C

2.2: 22 percent / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 2 h / -78 °C

With n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane;
DOI:10.1021/ol034823f

Reference yield:

: 596092-40-9
(E)-(R)-1-[(4S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-penta-2,4-dien-1-ol

: 2,2-Dimethyl-propionic acid (3aS,4R,4aS,9aR)-2,2-dimethyl-9-oxo-8-(toluene-4-sulfonyl)-3a,4,4a,7,9,9a-hexahydro-naphtho[2,3-d][1,3]dioxol-4-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1: pyridine; DMAP / CH₂Cl₂ / 12 h / Heating

2: tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

3: oxalyl chloride; DMSO / CH₂Cl₂ / 0.58 h / -78 °C

4: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / -78 °C

5: 62 percent / Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

With pyridine; dmap; oxalyl dichloride; tetrabutyl ammonium fluoride; Dess-Martin periodane; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; 5: intramolecular Diels-Alder cycloaddition;
DOI:10.1021/ol034823f