(Z)-N,N-diethyl-6-O-t-butyldiphenylsilyl-2,3-dideoxy-4,5-O-isopropylidene-D-threo-hex-2-enamide

Base Information

Chemical Name:(Z)-N,N-diethyl-6-O-t-butyldiphenylsilyl-2,3-dideoxy-4,5-O-isopropylidene-D-threo-hex-2-enamide
CAS No.:1450618-25-3
Molecular Formula:C₂₉H₄₁NO₄Si
Molecular Weight:495.734
Hs Code.:

Synonyms:(Z)-N,N-diethyl-6-O-t-butyldiphenylsilyl-2,3-dideoxy-4,5-O-isopropylidene-D-threo-hex-2-enamide

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (Z)-N,N-diethyl-6-O-t-butyldiphenylsilyl-2,3-dideoxy-4,5-O-isopropylidene-D-threo-hex-2-enamide

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Technology Process of (Z)-N,N-diethyl-6-O-t-butyldiphenylsilyl-2,3-dideoxy-4,5-O-isopropylidene-D-threo-hex-2-enamide

There total 2 articles about (Z)-N,N-diethyl-6-O-t-butyldiphenylsilyl-2,3-dideoxy-4,5-O-isopropylidene-D-threo-hex-2-enamide 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: 26.0%

: 104584-00-1
dimethyl (2-(diethylamino)-2-oxoethyl)phosphonate

: 169871-37-8
(4R,5S)-trans-2,2-dimethyl-4-tert-butyldiphenylsiloxymethyl-5-formyl-1,3-dioxolane

: 1450618-24-2
(E)-N,N-diethyl-6-O-t-butyldiphenylsilyl-2,3-dideoxy-4,5-O-isopropylidene-D-threo-hex-2-enamide

: 1450618-25-3
(Z)-N,N-diethyl-6-O-t-butyldiphenylsilyl-2,3-dideoxy-4,5-O-isopropylidene-D-threo-hex-2-enamide

Guidance literature:: dimethyl (2-(diethylamino)-2-oxoethyl)phosphonate; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.166667h; Inert atmosphere;

(4R,5S)-trans-2,2-dimethyl-4-tert-butyldiphenylsiloxymethyl-5-formyl-1,3-dioxolane; In tetrahydrofuran; hexane; at -78 ℃; for 2h; Overall yield = 72 %; Inert atmosphere;
DOI:10.1002/ejoc.201300322

Reference yield:

: 2430-01-5
2-bromo-N,N-diethylacetamide

: 1450618-25-3
(Z)-N,N-diethyl-6-O-t-butyldiphenylsilyl-2,3-dideoxy-4,5-O-isopropylidene-D-threo-hex-2-enamide

Guidance literature:: Multi-step reaction with 2 steps

1.1: ethyl acetate / 72 h / Reflux

2.1: n-butyllithium / hexane; tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere

2.2: 2 h / -78 °C / Inert atmosphere

With n-butyllithium; In tetrahydrofuran; hexane; ethyl acetate; 2.1: |Horner-Wadsworth-Emmons Olefination / 2.2: |Horner-Wadsworth-Emmons Olefination;
DOI:10.1002/ejoc.201300322

Reference yield: 76.0%

: 56-23-5
tetrachloromethane

: 1450618-25-3
(Z)-N,N-diethyl-6-O-t-butyldiphenylsilyl-2,3-dideoxy-4,5-O-isopropylidene-D-threo-hex-2-enamide

: 1450618-37-7
2-chloro-N,N-diethyl-3-(3-O-t-butyldiphenylsilyl-1,2-isopropilidene-D-threitol-1-yl)cyclopropanecarboxamide

Guidance literature:: With chromium dichloride; In tetrahydrofuran; for 16h; stereoselective reaction; Inert atmosphere; Reflux;
DOI:10.1002/ejoc.201300322