(3R,5S)-3-(3-bromo-2-methylenepropyl)-5-<(tert-butyldiphenylsilyloxy)methyl>-4,5-dihydro-2(3H)-furanone

Base Information

Chemical Name:(3R,5S)-3-(3-bromo-2-methylenepropyl)-5-<(tert-butyldiphenylsilyloxy)methyl>-4,5-dihydro-2(3H)-furanone
CAS No.:162518-02-7
Molecular Formula:C₂₅H₃₁BrO₃Si
Molecular Weight:487.509
Hs Code.:

Synonyms:(3R,5S)-3-(3-bromo-2-methylenepropyl)-5-<(tert-butyldiphenylsilyloxy)methyl>-4,5-dihydro-2(3H)-furanone

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Chemical Property of (3R,5S)-3-(3-bromo-2-methylenepropyl)-5-<(tert-butyldiphenylsilyloxy)methyl>-4,5-dihydro-2(3H)-furanone

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Technology Process of (3R,5S)-3-(3-bromo-2-methylenepropyl)-5-<(tert-butyldiphenylsilyloxy)methyl>-4,5-dihydro-2(3H)-furanone

There total 1 articles about (3R,5S)-3-(3-bromo-2-methylenepropyl)-5-<(tert-butyldiphenylsilyloxy)methyl>-4,5-dihydro-2(3H)-furanone 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: 74.0%

: 159691-84-6
(3R,5S)-<(tert-butyldiphenylsilyloxy)methyl>-4,5-dihydro-3-<2-methylene-3-(tetrahydropyran-2-yloxy)propyl>-2(3H)-furanone

: 162518-02-7
(3R,5S)-3-(3-bromo-2-methylenepropyl)-5-<(tert-butyldiphenylsilyloxy)methyl>-4,5-dihydro-2(3H)-furanone

Guidance literature:: With bromine; triphenylphosphine; In dichloromethane; at -20 ℃; for 3h;

Reference yield:

: 162518-02-7
(3R,5S)-3-(3-bromo-2-methylenepropyl)-5-<(tert-butyldiphenylsilyloxy)methyl>-4,5-dihydro-2(3H)-furanone

: 1-(tert-butyldiphenylsilyloxy)-3-<6-<6-<<(tert-butyldiphenylsilyloxy)methyl>-2,2-dimethyl-1,3-dioxan-4-yl>methyl>-2,2-dimethyl-1,3-dioxan-4-yl>-2-propanol

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) 1.50m n-BuLi, diisopropylamine / 1.) hexane, THF, -78 deg C, 1 h; 2.) hexane, THF, -78 deg C, 2.5 h then 10 min at room temp.

2: 21 percent / 2.20M n-BuLi, diisopropylamine, chlorotrimethylsilane / hexane; tetrahydrofuran / 1 h / -78 °C

4: 88 percent / camphorsulfonic acid / acetone / 0.5 h

5: 1.) O₃; 2.) NEt₃, NaI / 1.) CH₂Cl₂, CH₃OH, -78 deg C; 2.) CH₂Cl₂, CH₃OH, 3 h, room temp.

6: 2M Zn(BH₄)2 / toluene; diethyl ether / 5 h / -63 °C

7: camphorsulfonic acid / acetone / 3 h

With n-butyllithium; chloro-trimethyl-silane; zinc(II) tetrahydroborate; camphor-10-sulfonic acid; ozone; triethylamine; diisopropylamine; sodium iodide; In tetrahydrofuran; diethyl ether; hexane; acetone; toluene;

Reference yield:

: 162518-02-7
(3R,5S)-3-(3-bromo-2-methylenepropyl)-5-<(tert-butyldiphenylsilyloxy)methyl>-4,5-dihydro-2(3H)-furanone

: 162428-16-2
(2S,4'S,6'S,4''R,6''S)-1-(tert-butyldiphenylsilyloxy)-3-<6-<6-<<(tert-butyldiphenylsilyloxy)methyl>-2,2-dimethyl-1,3-dioxan-4-yl>methyl>-2,2-dimethyl-1,3-dioxan-4-yl>-2-propanol

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) 1.50m n-BuLi, diisopropylamine / 1.) hexane, THF, -78 deg C, 1 h; 2.) hexane, THF, -78 deg C, 2.5 h then 10 min at room temp.

3: 89 percent / camphorsulfonic acid / acetone / 0.5 h

4: 1.) O₃; 2.) NEt₃, NaI / 1.) CH₂Cl₂, CH₃OH, -78 deg C; 2.) CH₂Cl₂, CH₃OH, 3 h, room temp.

5: LiAlH₄ / diethyl ether / 1 h at -78 deg C, 1 h at room temp.

6: camphorsulfonic acid / acetone / 10 h

With lithium aluminium tetrahydride; n-butyllithium; camphor-10-sulfonic acid; ozone; triethylamine; diisopropylamine; sodium iodide; In diethyl ether; acetone;