N-{(2S)-2-[(4R,5S,6R)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-5-methyl-1-cyclohexenyl]-2-hydroxyethyl}-isoindoline-1,3-dione

Base Information

Chemical Name:N-{(2S)-2-[(4R,5S,6R)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-5-methyl-1-cyclohexenyl]-2-hydroxyethyl}-isoindoline-1,3-dione
CAS No.:1309930-36-6
Molecular Formula:C₃₀H₃₉NO₅Si
Molecular Weight:521.729
Hs Code.:

Synonyms:N-{(2S)-2-[(4R,5S,6R)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-5-methyl-1-cyclohexenyl]-2-hydroxyethyl}-isoindoline-1,3-dione

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Chemical Property of N-{(2S)-2-[(4R,5S,6R)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-5-methyl-1-cyclohexenyl]-2-hydroxyethyl}-isoindoline-1,3-dione

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Technology Process of N-{(2S)-2-[(4R,5S,6R)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-5-methyl-1-cyclohexenyl]-2-hydroxyethyl}-isoindoline-1,3-dione

There total 8 articles about N-{(2S)-2-[(4R,5S,6R)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-5-methyl-1-cyclohexenyl]-2-hydroxyethyl}-isoindoline-1,3-dione 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: 53.0%

: 2913-97-5
N-phthalimidyl-2-aminoacetaldehyde

: 1309930-46-8
[(1R,5R,6S)-5-benzyloxy-4-iodo-6-methylcyclohex-3-enyloxy]-tert-butyldimethylsilane

: C₂₀H₃₂O₂Si

: 1309930-36-6
N-{(2S)-2-[(4R,5S,6R)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-5-methyl-1-cyclohexenyl]-2-hydroxyethyl}-isoindoline-1,3-dione

Guidance literature:: With chromium dichloride; nickel dichloride; In N,N-dimethyl-formamide; at 28 ℃; for 36h; stereoselective reaction;
DOI:10.1039/c0ob01118e

Reference yield:

: 1309930-37-7
(5R,6R)-5-tert-butyldimethylsilyloxy-6-methyl-2-cyclohexenone

: C₂₀H₃₂O₂Si

: 1309930-36-6
N-{(2S)-2-[(4R,5S,6R)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-5-methyl-1-cyclohexenyl]-2-hydroxyethyl}-isoindoline-1,3-dione

Guidance literature:: Multi-step reaction with 4 steps

1.1: dmap; iodine / dichloromethane / 10.3 h / 20 °C

2.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol; dichloromethane / 0.5 h / 0 °C

3.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

3.2: 12 h / 20 °C / Inert atmosphere

4.1: chromium dichloride; nickel dichloride / N,N-dimethyl-formamide / 36 h / 28 °C

With chromium dichloride; dmap; sodium tetrahydroborate; cerium(III) chloride heptahydrate; iodine; sodium hydride; nickel dichloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 2.1: Luche reduction / 4.1: Nozaki-Hiyama-Kishi reaction;
DOI:10.1039/c0ob01118e

Reference yield:

: 1309930-42-4
(5R,6R)-5-tert-butyldimethylsilyloxy-2-iodo-6-methyl-2-cyclohexenone

: C₂₀H₃₂O₂Si

: 1309930-36-6
N-{(2S)-2-[(4R,5S,6R)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-5-methyl-1-cyclohexenyl]-2-hydroxyethyl}-isoindoline-1,3-dione

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol; dichloromethane / 0.5 h / 0 °C

2.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

2.2: 12 h / 20 °C / Inert atmosphere

3.1: chromium dichloride; nickel dichloride / N,N-dimethyl-formamide / 36 h / 28 °C

With chromium dichloride; sodium tetrahydroborate; cerium(III) chloride heptahydrate; sodium hydride; nickel dichloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Luche reduction / 3.1: Nozaki-Hiyama-Kishi reaction;
DOI:10.1039/c0ob01118e