(4S,5S)-4-(tert-Butyldimethylsilyloxymethyl)-5-[(3S,4S,1E)-4-tert-butyldiphenylsilyloxy-3-(2,2,2-trifluoroacetimidoyloxy)pentenyl]-2,2-dimethyl-1,3-dioxolane

Base Information

Chemical Name:(4S,5S)-4-(tert-Butyldimethylsilyloxymethyl)-5-[(3S,4S,1E)-4-tert-butyldiphenylsilyloxy-3-(2,2,2-trifluoroacetimidoyloxy)pentenyl]-2,2-dimethyl-1,3-dioxolane
CAS No.:125941-81-3
Molecular Formula:C₃₅H₅₂F₃NO₅Si₂
Molecular Weight:679.968
Hs Code.:

(4S,5S)-4-(tert-Butyldimethylsilyloxymethyl)-5-[(3S,4S,1E)-4-tert-butyldiphenylsilyloxy-3-(2,2,2-trifluoroacetimidoyloxy)pentenyl]-2,2-dimethyl-1,3-dioxolane

Synonyms:(4S,5S)-4-(tert-Butyldimethylsilyloxymethyl)-5-[(3S,4S,1E)-4-tert-butyldiphenylsilyloxy-3-(2,2,2-trifluoroacetimidoyloxy)pentenyl]-2,2-dimethyl-1,3-dioxolane

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Chemical Property of (4S,5S)-4-(tert-Butyldimethylsilyloxymethyl)-5-[(3S,4S,1E)-4-tert-butyldiphenylsilyloxy-3-(2,2,2-trifluoroacetimidoyloxy)pentenyl]-2,2-dimethyl-1,3-dioxolane

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Technology Process of (4S,5S)-4-(tert-Butyldimethylsilyloxymethyl)-5-[(3S,4S,1E)-4-tert-butyldiphenylsilyloxy-3-(2,2,2-trifluoroacetimidoyloxy)pentenyl]-2,2-dimethyl-1,3-dioxolane

There total 11 articles about (4S,5S)-4-(tert-Butyldimethylsilyloxymethyl)-5-[(3S,4S,1E)-4-tert-butyldiphenylsilyloxy-3-(2,2,2-trifluoroacetimidoyloxy)pentenyl]-2,2-dimethyl-1,3-dioxolane 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: 81.0%

: 353-85-5
trifluoroacetonitrile

: 125941-79-9
(4S,5S)-4-(tert-Butyldimethylsilyloxymethyl)-5-[(3S,4S,1E)-4-tert-butyldiphenylsilyloxy-3-hydroxopentenyl]-2,2-dimethyl-1,3-dioxolane

: 125941-81-3
(4S,5S)-4-(tert-Butyldimethylsilyloxymethyl)-5-[(3S,4S,1E)-4-tert-butyldiphenylsilyloxy-3-(2,2,2-trifluoroacetimidoyloxy)pentenyl]-2,2-dimethyl-1,3-dioxolane

Guidance literature:: (4S,5S)-4-(tert-Butyldimethylsilyloxymethyl)-5-[(3S,4S,1E)-4-tert-butyldiphenylsilyloxy-3-hydroxopentenyl]-2,2-dimethyl-1,3-dioxolane; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

trifluoroacetonitrile; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 1h;
DOI:10.1039/a905772b

Reference yield: 75.0%

: 353-85-5
trifluoroacetonitrile

: (E)-(3S,4S)-1-[(3S,4S)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-[1,2]dioxetan-3-yl]-4-(tert-butyl-diphenyl-silanyloxy)-pent-1-en-3-ol

: 125941-81-3
(4S,5S)-4-(tert-Butyldimethylsilyloxymethyl)-5-[(3S,4S,1E)-4-tert-butyldiphenylsilyloxy-3-(2,2,2-trifluoroacetimidoyloxy)pentenyl]-2,2-dimethyl-1,3-dioxolane

Guidance literature:: With n-butyllithium; molecular sieve; In tetrahydrofuran; at -78 ℃; for 0.5h;
DOI:10.1039/c39890000717

Reference yield:

: 102732-44-5
ethyl (S)-2-(tert-butyldiphenylsilyloxy)propanoate

: 125941-81-3
(4S,5S)-4-(tert-Butyldimethylsilyloxymethyl)-5-[(3S,4S,1E)-4-tert-butyldiphenylsilyloxy-3-(2,2,2-trifluoroacetimidoyloxy)pentenyl]-2,2-dimethyl-1,3-dioxolane

Guidance literature:: Multi-step reaction with 6 steps

1.1: KOH; MeOH

2.1: DCC / ethyl acetate / 9 h / 20 °C

3.1: BuLi / tetrahydrofuran; hexane / 0.08 h / 20 °C

3.2: 75 percent / tetrahydrofuran; hexane / 0.5 h / 20 °C

4.1: 85 percent / benzene / 5 h / Heating

5.1: 90 percent / lithium tri-sec-butylborohydride / tetrahydrofuran / 0.67 h / -78 °C

6.1: BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

6.2: 81 percent / tetrahydrofuran; hexane / 1 h / -78 - 20 °C

With methanol; potassium hydroxide; n-butyllithium; L-Selectride; dicyclohexyl-carbodiimide; In tetrahydrofuran; hexane; ethyl acetate; benzene; 1.1: Saponification / 2.1: Acylation / 3.1: Elimination / 3.2: Condensation / 4.1: Condensation / 5.1: Reduction / 6.1: Metallation / 6.2: Addition;
DOI:10.1039/a905772b