(3S,6R,7R,8R,8aS)-3-(tert-butyldiphenylsilyloxymethyl)-6,7,8-trihydroxyindolizidin-5-one

Base Information

• Chemical Name: (3S,6R,7R,8R,8aS)-3-(tert-butyldiphenylsilyloxymethyl)-6,7,8-trihydroxyindolizidin-5-one
• CAS No.: 244274-71-3
• Molecular Formula: C₂₅H₃₃NO₅Si
• Molecular Weight: 455.626

Synonyms:(3S,6R,7R,8R,8aS)-3-(tert-butyldiphenylsilyloxymethyl)-6,7,8-trihydroxyindolizidin-5-one

Chemical Property of (3S,6R,7R,8R,8aS)-3-(tert-butyldiphenylsilyloxymethyl)-6,7,8-trihydroxyindolizidin-5-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,6R,7R,8R,8aS)-3-(tert-butyldiphenylsilyloxymethyl)-6,7,8-trihydroxyindolizidin-5-one

There total 10 articles about (3S,6R,7R,8R,8aS)-3-(tert-butyldiphenylsilyloxymethyl)-6,7,8-trihydroxyindolizidin-5-one 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: 84.0%

(3R,4R,5R,2'S,5'S)-5-[1'-(tert-butoxycarbonyl)-5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'-yl]-3,4-dihydroxytetrahydrofuran-2-one (244274-70-2) → (3S,6R,7R,8R,8aS)-3-(tert-butyldiphenylsilyloxymethyl)-6,7,8-trihydroxyindolizidin-5-one (244274-71-3)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; thiophenol; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1002/(SICI)1099-0690(199906)1999:6<1395::AID-EJOC1395>3.0.CO;2-T

Reference yield:

4-<(tert-butoxycarbonyl)amino>-6,7-O-isopropylidene-2,3,4-trideoxy-L-arabino-hept-2-enonic acid 1,4-lactam (141393-87-5) → (3S,6R,7R,8R,8aS)-3-(tert-butyldiphenylsilyloxymethyl)-6,7,8-trihydroxyindolizidin-5-one (244274-71-3)

Guidance literature:

Multi-step reaction with 10 steps

1: 90 percent / H₂; NaOAc / Pd/C / tetrahydrofuran / 24 h / 20 °C

2: AcOH; water / 8 h / 50 °C

3: NaIO₄ / CH₂Cl₂; H₂O / 0.25 h

4: 5.2 g / NaBH₄ / methanol / -30 - -15 °C

5: 83 percent / imidazole / dimethylformamide / 18 h / 20 °C

6: LiEt₃BH / tetrahydrofuran / 3 h / -78 °C

7: BF₃*OEt₂ / diethyl ether / 0.5 h / 20 °C

8: 78 percent / TBSOTf / CH₂Cl₂ / 1 h / -80 °C

9: 72 percent / cis-dicyclohexano-18-crown-6 ether; KMnO₄ / CH₂Cl₂ / 4 h

10: 84 percent / thiophenol; TMSOTf / CH₂Cl₂ / 1 h / 0 °C

With 1H-imidazole; sodium tetrahydroborate; potassium permanganate; sodium periodate; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; t-butyldimethylsiyl triflate; water; hydrogen; sodium acetate; dicyclohexano-18-crown-6; lithium triethylborohydride; acetic acid; thiophenol; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; 1: Catalytic hydrogenation / 2: Hydrolysis / 3: Oxidation / 4: Reduction / 5: Substitution / 6: Reduction / 7: Alkylation / 8: Mannich reaction / 9: Oxidation / 10: Decarboxylation;

DOI:10.1002/(SICI)1099-0690(199906)1999:6<1395::AID-EJOC1395>3.0.CO;2-T

Reference yield:

(S)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-5-oxopyrrolidine-1-carboxylate (138629-30-8,138871-56-4) → (3S,6R,7R,8R,8aS)-3-(tert-butyldiphenylsilyloxymethyl)-6,7,8-trihydroxyindolizidin-5-one (244274-71-3)

Guidance literature:

Multi-step reaction with 5 steps

1: LiEt₃BH / tetrahydrofuran / 3 h / -78 °C

2: BF₃*OEt₂ / diethyl ether / 0.5 h / 20 °C

3: 78 percent / TBSOTf / CH₂Cl₂ / 1 h / -80 °C

4: 72 percent / cis-dicyclohexano-18-crown-6 ether; KMnO₄ / CH₂Cl₂ / 4 h

5: 84 percent / thiophenol; TMSOTf / CH₂Cl₂ / 1 h / 0 °C

With potassium permanganate; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; t-butyldimethylsiyl triflate; dicyclohexano-18-crown-6; lithium triethylborohydride; thiophenol; In tetrahydrofuran; diethyl ether; dichloromethane; 1: Reduction / 2: Alkylation / 3: Mannich reaction / 4: Oxidation / 5: Decarboxylation;

DOI:10.1002/(SICI)1099-0690(199906)1999:6<1395::AID-EJOC1395>3.0.CO;2-T

upstream raw materials:

(3R,4R,5R,2'S,5'S)-5-[1'-(tert-butoxycarbonyl)-5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'-yl]-3,4-dihydroxytetrahydrofuran-2-one

(S)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-5-oxopyrrolidine-1-carboxylate

2-hydroxymethyl-5-oxopyrrolidine-1-carboxylic acid tert-butyl ester

tert-butyl (S)-2-formyl-5-oxopyrrolidine-1-carboxylate

Downstream raw materials:

(3S,6R,7R,8R,8aS)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-6,7,8-tris-trimethylsilanyloxy-hexahydro-indolizin-5-one

(3S,6S,7S,8R,8aS)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-6,7,8-tris-trimethylsilanyloxy-octahydro-indolizine

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 244274-71-3 (3S,6R,7R,8R,8aS)-3-(tert-butyldiphenylsilyloxymethyl)-6,7,8-trihydroxyindolizidin-5-one

Send

Send

Metric Ton KG G Pound L ML

Send

Send