(2S,4R,5S)-4-O-t-butyldimethylsilyl-1,2-O-isopropylidene-1,2,4,5-tetrahydroxy-5-(p-chlorophenyl)pentan-3-one

Base Information

Chemical Name:(2S,4R,5S)-4-O-t-butyldimethylsilyl-1,2-O-isopropylidene-1,2,4,5-tetrahydroxy-5-(p-chlorophenyl)pentan-3-one
CAS No.:220820-72-4
Molecular Formula:C₂₀H₃₁ClO₅Si
Molecular Weight:415.002
Hs Code.:

Synonyms:(2S,4R,5S)-4-O-t-butyldimethylsilyl-1,2-O-isopropylidene-1,2,4,5-tetrahydroxy-5-(p-chlorophenyl)pentan-3-one

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Chemical Property of (2S,4R,5S)-4-O-t-butyldimethylsilyl-1,2-O-isopropylidene-1,2,4,5-tetrahydroxy-5-(p-chlorophenyl)pentan-3-one

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Technology Process of (2S,4R,5S)-4-O-t-butyldimethylsilyl-1,2-O-isopropylidene-1,2,4,5-tetrahydroxy-5-(p-chlorophenyl)pentan-3-one

There total 1 articles about (2S,4R,5S)-4-O-t-butyldimethylsilyl-1,2-O-isopropylidene-1,2,4,5-tetrahydroxy-5-(p-chlorophenyl)pentan-3-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: 86.0%

: 104-88-1
4-chlorobenzaldehyde

: 115043-29-3
2-(tert-Butyl-dimethyl-silanyloxy)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanone

: 220820-72-4
(2S,4R,5S)-4-O-t-butyldimethylsilyl-1,2-O-isopropylidene-1,2,4,5-tetrahydroxy-5-(p-chlorophenyl)pentan-3-one

Guidance literature:: 2-(tert-Butyl-dimethyl-silanyloxy)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanone; With dicyclohexylboron chloride; triethylamine; In diethyl ether; at -78 - 0 ℃; for 1h;

4-chlorobenzaldehyde; In water; at 0 ℃; for 5h;

With dihydrogen peroxide; In methanol; phosphate buffer; at 20 ℃; for 1h; pH=7;
DOI:10.1016/S0040-4020(99)01041-8

Reference yield: 71.0%

: 186581-53-3,908094-01-9,334-88-3
diazomethane

: 220820-72-4
(2S,4R,5S)-4-O-t-butyldimethylsilyl-1,2-O-isopropylidene-1,2,4,5-tetrahydroxy-5-(p-chlorophenyl)pentan-3-one

: 262844-01-9
methyl (2R,3S)-2-O-t-butyldimethylsilyl-3-O-formyl-2,3-dihydroxy-3-(p-chlorophenyl)propionate

: 262844-05-3
methyl (2R,3S)-2-O-t-butyldimethylsilyl-2,3-dihydroxy-3-(p-chlorophenyl)propionate

Guidance literature:: (2S,4R,5S)-4-O-t-butyldimethylsilyl-1,2-O-isopropylidene-1,2,4,5-tetrahydroxy-5-(p-chlorophenyl)pentan-3-one; With periodic acid; In ethyl acetate; at 20 ℃; for 2h;

diazomethane; In diethyl ether;
DOI:10.1016/S0040-4020(99)01041-8

Reference yield:

: 186581-53-3,908094-01-9,334-88-3
diazomethane

: 220820-72-4
(2S,4R,5S)-4-O-t-butyldimethylsilyl-1,2-O-isopropylidene-1,2,4,5-tetrahydroxy-5-(p-chlorophenyl)pentan-3-one

: 206346-40-9
methyl (2R,3S)-2,3-dihydroxy-3-(4'-chlorophenyl)propanoate

Guidance literature:: (2S,4R,5S)-4-O-t-butyldimethylsilyl-1,2-O-isopropylidene-1,2,4,5-tetrahydroxy-5-(p-chlorophenyl)pentan-3-one; With periodic acid; In ethyl acetate; at 20 ℃; for 2h;

diazomethane; In diethyl ether;

With hydrogen fluoride; In acetonitrile; at 20 ℃; for 6h;
DOI:10.1016/S0040-4020(99)01041-8