4-[(4R,5S,6R)-6-[(S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-2-methyl-but-3-enoyl]-5-(3,4-dimethoxy-benzyloxy)-[1,3]dioxan-4-yl]-piperidine-2,6-dione

Base Information

Chemical Name:4-[(4R,5S,6R)-6-[(S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-2-methyl-but-3-enoyl]-5-(3,4-dimethoxy-benzyloxy)-[1,3]dioxan-4-yl]-piperidine-2,6-dione
CAS No.:104777-85-7
Molecular Formula:C₃₀H₄₅NO₉Si
Molecular Weight:591.774
Hs Code.:

Synonyms:4-[(4R,5S,6R)-6-[(S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-2-methyl-but-3-enoyl]-5-(3,4-dimethoxy-benzyloxy)-[1,3]dioxan-4-yl]-piperidine-2,6-dione

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Chemical Property of 4-[(4R,5S,6R)-6-[(S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-2-methyl-but-3-enoyl]-5-(3,4-dimethoxy-benzyloxy)-[1,3]dioxan-4-yl]-piperidine-2,6-dione

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Technology Process of 4-[(4R,5S,6R)-6-[(S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-2-methyl-but-3-enoyl]-5-(3,4-dimethoxy-benzyloxy)-[1,3]dioxan-4-yl]-piperidine-2,6-dione

There total 22 articles about 4-[(4R,5S,6R)-6-[(S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-2-methyl-but-3-enoyl]-5-(3,4-dimethoxy-benzyloxy)-[1,3]dioxan-4-yl]-piperidine-2,6-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: 60.0%

: 104777-84-6,104833-79-6
4-[(4R,5S,6S)-6-[(1S,2S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-1-hydroxy-2-methyl-but-3-enyl]-5-(3,4-dimethoxy-benzyloxy)-[1,3]dioxan-4-yl]-piperidine-2,6-dione

: 104777-85-7
4-[(4R,5S,6R)-6-[(S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-2-methyl-but-3-enoyl]-5-(3,4-dimethoxy-benzyloxy)-[1,3]dioxan-4-yl]-piperidine-2,6-dione

Guidance literature:: With pyridine; chromium(VI) oxide; In acetic anhydride; Ambient temperature;
DOI:10.1039/c39860000396

Reference yield:

: 113473-80-6
4-((4S,5R,6R)-5-Benzyloxy-6-benzyloxymethyl-[1,3]dioxan-4-yl)-piperidine-2,6-dione

: 104777-85-7
4-[(4S,5R,6S)-6-[(R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-2-methyl-but-3-enoyl]-5-(3,4-dimethoxy-benzyloxy)-[1,3]dioxan-4-yl]-piperidine-2,6-dione

Guidance literature:: Multi-step reaction with 6 steps

1: H₂ / Pd/C / methanol / 4 h

2: p. TsOH monohydrate / toluene / 5 h / Heating; azeotropic removal of water

3: diethylaluminium chloride, triethylsilane / toluene; CH₂Cl₂ / 1.5 h / -60 - -55 °C

4: CrO₃, pyridine, acetic anhydride / CH₂Cl₂; dimethylformamide / 0.13 h / Ambient temperature

5: BF₃*Et₂O / CH₂Cl₂ / 1 h / -90 - -80 °C

6: CrO₃, pyridine, acetic anhydride / CH₂Cl₂; dimethylformamide / 0.13 h / Ambient temperature

With pyridine; chromium(VI) oxide; triethylsilane; boron trifluoride diethyl etherate; hydrogen; diethylaluminium chloride; acetic anhydride; toluene-4-sulfonic acid; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4020(01)81662-8

Reference yield:

: 102487-45-6,102518-68-3,112419-11-1
4-((4R,5S,6S)-5-Hydroxy-6-hydroxymethyl-[1,3]dioxan-4-yl)-piperidine-2,6-dione

: 104777-85-7
4-[(4R,5S,6R)-6-[(S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-2-methyl-but-3-enoyl]-5-(3,4-dimethoxy-benzyloxy)-[1,3]dioxan-4-yl]-piperidine-2,6-dione

Guidance literature:: Multi-step reaction with 5 steps

1: 96 percent

2: 61 percent / Et₂AlCl, Et₃SiH / CH₂Cl₂ / -55 °C

3: 65 percent / CrO₃, pyridine / acetic anhydride / Ambient temperature

4: BF₃*Et₂O / CH₂Cl₂ / -90 °C

5: 60 percent / CrO₃, pyridine / acetic anhydride / Ambient temperature

With pyridine; chromium(VI) oxide; triethylsilane; boron trifluoride diethyl etherate; diethylaluminium chloride; In dichloromethane; acetic anhydride;
DOI:10.1039/c39860000396