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

Base Information

• Chemical Name: 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
• CAS No.: 102615-87-2
• Molecular Formula: C₃₇H₅₃NO₇Si₂
• Molecular Weight: 680.001
• Mol file: 102615-87-2.mol

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 18 articles about 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 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: 63.0%

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) → 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 (102615-87-2)

Guidance literature:

Swern oxidation;

DOI:10.1021/jo00363a051

Reference yield:

(4R,4aS,8aS)-4-(Tetrahydro-[1,3]dioxino[5,4-d][1,3]dioxin-4-yl)-piperidine-2,6-dione (93125-65-6) → 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 (102615-87-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 87 percent / trifluoroacetic anhydride (TFAA) / 6 h / 22 °C

2: 100 percent / 2,6-lutidine / CH₂Cl₂

3: 97 percent / diisobutylaluminum hydride (DiBAl-H) / tetrahydrofuran / 2 h / -78 - 0 °C

4: Swern oxidation

5: 1.) BF₃*Et₂O, 2.) aq. NaHCO₃ / 1.) CH₂Cl₂, -78 deg C, 5.5 h, 2.) CH₂Cl₂, -78 deg C

6: Swern oxidation

With 2,6-dimethylpyridine; boron trifluoride diethyl etherate; diisobutylaluminium hydride; sodium hydrogencarbonate; trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00363a051

Reference yield:

(4R,4aS,8aS)-4-(Tetrahydro-[1,3]dioxino[5,4-d][1,3]dioxin-4-yl)-piperidine-2,6-dione (93125-65-6) → 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 (102615-87-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 87 percent / trifluoroacetic anhydride (TFAA) / 6 h / 22 °C

2: 100 percent / 2,6-lutidine / CH₂Cl₂

3: 97 percent / diisobutylaluminum hydride (DiBAl-H) / tetrahydrofuran / 2 h / -78 - 0 °C

4: Swern oxidation

5: 1.) BF₃*Et₂O, 2.) aq. NaHCO₃ / 1.) CH₂Cl₂, -78 deg C, 5.5 h, 2.) CH₂Cl₂, -78 deg C

6: 63 percent / Swern oxidation

With 2,6-dimethylpyridine; boron trifluoride diethyl etherate; diisobutylaluminium hydride; sodium hydrogencarbonate; trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00363a051

upstream raw materials:

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

(4R,4aS,8aS)-4-(Tetrahydro-[1,3]dioxino[5,4-d][1,3]dioxin-4-yl)-piperidine-2,6-dione

(E)-(4R,4aS,8aS)-3-(Tetrahydro-[1,3]dioxino[5,4-d][1,3]dioxin-4-yl)-acrylic acid ethyl ester

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

Downstream raw materials:

sesbanimide B

(-)-sesbanimide A