4-[(4R,5S,6S)-6-[(S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-1-hydroxy-2-methyl-but-3-enyl]-5-(tert-butyl-diphenyl-silanyloxy)-[1,3]dioxan-4-yl]-piperidine-2,6-dione

Base Information

• Chemical Name: 4-[(4R,5S,6S)-6-[(S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-1-hydroxy-2-methyl-but-3-enyl]-5-(tert-butyl-diphenyl-silanyloxy)-[1,3]dioxan-4-yl]-piperidine-2,6-dione
• CAS No.: 102615-86-1
• Molecular Formula: C₃₇H₅₅NO₇Si₂
• Molecular Weight: 682.017

Synonyms:

Chemical Property of 4-[(4R,5S,6S)-6-[(S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-1-hydroxy-2-methyl-but-3-enyl]-5-(tert-butyl-diphenyl-silanyloxy)-[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-[(4R,5S,6S)-6-[(S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-1-hydroxy-2-methyl-but-3-enyl]-5-(tert-butyl-diphenyl-silanyloxy)-[1,3]dioxan-4-yl]-piperidine-2,6-dione

There total 46 articles about 4-[(4R,5S,6S)-6-[(S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-1-hydroxy-2-methyl-but-3-enyl]-5-(tert-butyl-diphenyl-silanyloxy)-[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:

tert-Butyl-dimethyl-((Z)-2-tributylstannanylmethyl-but-2-enyloxy)-silane (102615-85-0) + (4R,5S,6R)-5-(tert-Butyl-diphenyl-silanyloxy)-6-(2,6-dioxo-piperidin-4-yl)-[1,3]dioxane-4-carbaldehyde (102615-84-9) → 4-[(4R,5S,6S)-6-[(R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-1-hydroxy-2-methyl-but-3-enyl]-5-(tert-butyl-diphenyl-silanyloxy)-[1,3]dioxan-4-yl]-piperidine-2,6-dione (102615-86-1,102680-30-8,102680-32-0,120019-89-8,120019-91-2,120021-01-4,120052-32-6) + 4-[(4R,5S,6S)-6-[(S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-1-hydroxy-2-methyl-but-3-enyl]-5-(tert-butyl-diphenyl-silanyloxy)-[1,3]dioxan-4-yl]-piperidine-2,6-dione (102615-86-1,102680-30-8,102680-32-0,120019-89-8,120019-91-2,120021-01-4,120052-32-6)

Guidance literature:

With magnesium bromide ethyl etherate; In dichloromethane; at -40 ℃; for 48h; Yield given. Yields of byproduct given;

DOI:10.1021/jo00363a051

Reference yield:

tert-Butyl-dimethyl-((Z)-2-tributylstannanylmethyl-but-2-enyloxy)-silane (102615-85-0) + (4R,5S,6R)-5-(tert-Butyl-diphenyl-silanyloxy)-6-(2,6-dioxo-piperidin-4-yl)-[1,3]dioxane-4-carbaldehyde (102615-84-9) → 4-[(4R,5S,6S)-6-[(R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-1-hydroxy-2-methyl-but-3-enyl]-5-(tert-butyl-diphenyl-silanyloxy)-[1,3]dioxan-4-yl]-piperidine-2,6-dione (102615-86-1,102680-30-8,102680-32-0,120019-89-8,120019-91-2,120021-01-4,120052-32-6) + 4-[(4R,5S,6S)-6-[(S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-1-hydroxy-2-methyl-but-3-enyl]-5-(tert-butyl-diphenyl-silanyloxy)-[1,3]dioxan-4-yl]-piperidine-2,6-dione (102615-86-1,102680-30-8,102680-32-0,120019-89-8,120019-91-2,120021-01-4,120052-32-6)

Guidance literature:

With magnesium bromide ethyl etherate; In dichloromethane; at -40 ℃; for 48h; Yield given. Yields of byproduct given;

DOI:10.1021/jo00363a051

Reference yield:

4-((4S,5R,6R)-5-Benzyloxy-6-hydroxymethyl-[1,3]dioxan-4-yl)-piperidine-2,6-dione (119930-69-7) → 4-[(4S,5R,6R)-6-[(R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-1-hydroxy-2-methyl-but-3-enyl]-5-(tert-butyl-diphenyl-silanyloxy)-[1,3]dioxan-4-yl]-piperidine-2,6-dione (102615-86-1,102680-30-8,102680-32-0,120019-89-8,120019-91-2,120021-01-4,120052-32-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 92 percent / pyridine

2: 92 percent / H₂ / 10percent Pd-C / ethanol

3: 97 percent / 2,6-lutidine / CH₂Cl₂

4: 88 percent / DIBAH / CH₂Cl₂

5: 95 percent / CrO₃*Py / CH₂Cl₂

6: 18 percent / BF₃*Et₂O / CH₂Cl₂

With 2,6-dimethylpyridine; chromium trioxide-pyridine complex; boron trifluoride diethyl etherate; hydrogen; diisobutylaluminium hydride; palladium on activated charcoal; In pyridine; ethanol; dichloromethane;

DOI:10.1016/0040-4039(88)85094-9

upstream raw materials:

tert-Butyl-dimethyl-((Z)-2-tributylstannanylmethyl-but-2-enyloxy)-silane

(4S,5R,6S)-5-(tert-Butyl-diphenyl-silanyloxy)-6-(2,6-dioxo-piperidin-4-yl)-[1,3]dioxane-4-carbaldehyde

(4R,5S,6R)-5-Benzyloxy-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-[1,3]dioxane-4-carbaldehyde

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

Downstream raw materials:

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

sesbanimide B

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

(-)-sesbanimide A

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