(3R,4S,5S)-5-((S)-2'-(benzyloxy)-1'-(tert-butyl(dimethyl)silanyloxy)ethyl)-3,4-dihydroxy-4,5-dihydrofuran-2(3H)-one

Base Information

Chemical Name:(3R,4S,5S)-5-((S)-2'-(benzyloxy)-1'-(tert-butyl(dimethyl)silanyloxy)ethyl)-3,4-dihydroxy-4,5-dihydrofuran-2(3H)-one
CAS No.:872326-51-7
Molecular Formula:C₁₉H₃₀O₆Si
Molecular Weight:382.529
Hs Code.:

Synonyms:(3R,4S,5S)-5-((S)-2'-(benzyloxy)-1'-(tert-butyl(dimethyl)silanyloxy)ethyl)-3,4-dihydroxy-4,5-dihydrofuran-2(3H)-one

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Chemical Property of (3R,4S,5S)-5-((S)-2'-(benzyloxy)-1'-(tert-butyl(dimethyl)silanyloxy)ethyl)-3,4-dihydroxy-4,5-dihydrofuran-2(3H)-one

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Technology Process of (3R,4S,5S)-5-((S)-2'-(benzyloxy)-1'-(tert-butyl(dimethyl)silanyloxy)ethyl)-3,4-dihydroxy-4,5-dihydrofuran-2(3H)-one

There total 4 articles about (3R,4S,5S)-5-((S)-2'-(benzyloxy)-1'-(tert-butyl(dimethyl)silanyloxy)ethyl)-3,4-dihydroxy-4,5-dihydrofuran-2(3H)-one 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:

: 872326-43-7
(2Z,4E)-ethyl 6-(benzyloxy)hexa-2,4-dienoate

: 18162-48-6
tert-butyldimethylsilyl chloride

: 872326-51-7
(3R,4S,5S)-5-((S)-2'-(benzyloxy)-1'-(tert-butyl(dimethyl)silanyloxy)ethyl)-3,4-dihydroxy-4,5-dihydrofuran-2(3H)-one

: 5-[2-benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3,4-dihydroxy-dihydro-furan-2-one

Guidance literature:: (2Z,4E)-ethyl 6-(benzyloxy)hexa-2,4-dienoate; With osmium(VIII) oxide; potassium carbonate; potassium hexacyanoferrate(III); Hydroquinone 1,4-phthalazinediyl diether; methanesulfonamide; In water; tert-butyl alcohol; at 0 ℃;

tert-butyldimethylsilyl chloride; With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 12h;

With osmium(VIII) oxide; N-methyl-2-indolinone; In water; tert-butyl alcohol; at 0 ℃; Title compound not separated from byproducts;
DOI:10.1021/jo051476+

Reference yield:

: 69152-87-0
4-benzyloxycrotonaldehyde

: 872326-51-7
(3R,4S,5S)-5-((S)-2'-(benzyloxy)-1'-(tert-butyl(dimethyl)silanyloxy)ethyl)-3,4-dihydroxy-4,5-dihydrofuran-2(3H)-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: t-BuOK / 18-crown-6 / tetrahydrofuran / 0.25 h / -78 °C

1.2: tetrahydrofuran / 2.5 h / -78 °C

2.1: K₃Fe(CN)6; K₂CO₃; OsO₄ / (DHQ)2PHAL; MeSO₂NH₂ / 2-methyl-propan-2-ol; H₂O / 0 °C

2.2: imidazole / dimethylformamide / 12 h / 20 °C

3.1: NMO; OsO₄ / methanol; H₂O / 0 °C

With osmium(VIII) oxide; N-methyl-2-indolinone; potassium tert-butylate; potassium carbonate; potassium hexacyanoferrate(III); Hydroquinone 1,4-phthalazinediyl diether; 18-crown-6 ether; methanesulfonamide; In tetrahydrofuran; methanol; water; tert-butyl alcohol; 2.1: Sharpless dihydroxylation / 3.1: Sharpless dihydroxylation;
DOI:10.1021/jo051476+