4-[(4S,5R,6R)-6-[(1R,2R)-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

Base Information

• Chemical Name: 4-[(4S,5R,6R)-6-[(1R,2R)-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
• CAS No.: 104777-84-6
• Molecular Formula: C₃₀H₄₇NO₉Si
• Molecular Weight: 593.79

Synonyms:

Chemical Property of 4-[(4S,5R,6R)-6-[(1R,2R)-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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-[(4S,5R,6R)-6-[(1R,2R)-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

There total 36 articles about 4-[(4S,5R,6R)-6-[(1R,2R)-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 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: 18.5%

(Z)-1-(tert-Butyl-dimethyl-silanyloxy)-2-trimethylsilanylmethyl-but-2-ene (104777-89-1) + (4R,5S,6R)-5-(3,4-Dimethoxy-benzyloxy)-6-(2,6-dioxo-piperidin-4-yl)-[1,3]dioxane-4-carbaldehyde (104777-87-9) → 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 (104777-84-6,104833-79-6) + 4-[(4R,5S,6S)-6-[(1S,2R)-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 (104777-84-6,104833-79-6)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -90 - -80 ℃; for 1h;

DOI:10.1016/S0040-4020(01)81662-8

Reference yield: 18.5%

(Z)-1-(tert-Butyl-dimethyl-silanyloxy)-2-trimethylsilanylmethyl-but-2-ene (104777-89-1) + (4R,5S,6R)-5-(3,4-Dimethoxy-benzyloxy)-6-(2,6-dioxo-piperidin-4-yl)-[1,3]dioxane-4-carbaldehyde (104777-87-9) → 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 (104777-84-6,104833-79-6) + 4-[(4R,5S,6S)-6-[(1S,2R)-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 (104777-84-6,104833-79-6)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -90 - -80 ℃; for 1h;

DOI:10.1016/S0040-4020(01)81662-8

Reference yield:

4-((4S,5R,6R)-5-Benzyloxy-6-benzyloxymethyl-[1,3]dioxan-4-yl)-piperidine-2,6-dione (113473-80-6) → 4-[(4S,5R,6R)-6-[(1R,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 (104777-84-6,104833-79-6)

Guidance literature:

Multi-step reaction with 5 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

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

upstream raw materials:

(Z)-1-(tert-Butyl-dimethyl-silanyloxy)-2-trimethylsilanylmethyl-but-2-ene

(4R,5S,6R)-5-(3,4-Dimethoxy-benzyloxy)-6-(2,6-dioxo-piperidin-4-yl)-[1,3]dioxane-4-carbaldehyde

4-((4R,5S,6S)-5-Hydroxy-6-hydroxymethyl-[1,3]dioxan-4-yl)-piperidine-2,6-dione

Acetic acid (4S,5S,6R)-5-acetoxymethoxy-6-(2,6-dioxo-piperidin-4-yl)-[1,3]dioxan-4-ylmethyl ester

Downstream raw materials:

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

(-)-sesbanimide A

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

(+)-sesbanimide A

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