(-)-(6S,12S)-12-phenoxythionocarbonyloxy-7-aza-1,4-dioxadispiro[4,0,5,4]pentadecan-8-one

Base Information

• Chemical Name: (-)-(6S,12S)-12-phenoxythionocarbonyloxy-7-aza-1,4-dioxadispiro[4,0,5,4]pentadecan-8-one
• CAS No.: 244154-16-3
• Molecular Formula: C₁₉H₂₃NO₅S
• Molecular Weight: 377.461
• Mol file: 244154-16-3.mol

Synonyms:(-)-(6S,12S)-12-phenoxythionocarbonyloxy-7-aza-1,4-dioxadispiro[4,0,5,4]pentadecan-8-one

Chemical Property of (-)-(6S,12S)-12-phenoxythionocarbonyloxy-7-aza-1,4-dioxadispiro[4,0,5,4]pentadecan-8-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(6S,12S)-12-phenoxythionocarbonyloxy-7-aza-1,4-dioxadispiro[4,0,5,4]pentadecan-8-one

There total 15 articles about (-)-(6S,12S)-12-phenoxythionocarbonyloxy-7-aza-1,4-dioxadispiro[4,0,5,4]pentadecan-8-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: 87.0%

phenylcarbonochloridothioate (1005-56-7) + (+)-(6S,12S)-12-hydroxy-7-aza-1,4-dioxadispiro[4,0,5,4]pentadecan-8-one (244154-14-1) → (-)-(6S,12S)-12-phenoxythionocarbonyloxy-7-aza-1,4-dioxadispiro[4,0,5,4]pentadecan-8-one (244154-16-3)

Guidance literature:

With dmap; In dichloromethane; for 24h;

DOI:10.1021/jo990293i

Reference yield:

meso-(1r,2R,6S)-1-nitrocyclohexane-2,6-diol-1-acetaldehyde 1,3-propanediol acetal (244153-85-3) → (-)-(6S,12S)-12-phenoxythionocarbonyloxy-7-aza-1,4-dioxadispiro[4,0,5,4]pentadecan-8-one (244154-16-3)

Guidance literature:

Multi-step reaction with 14 steps

1: 81 percent / DMAP / CH₂Cl₂ / 2 h

2: hydrogen / Raney nickel / tetrahydrofuran / 14 h / 60 °C / 760 Torr

3: 3.24 g / pyridine / 1 h / Heating

4: aqueous acetic acid / 1 h / 20 °C / ultrasound

5: 144 mg / triethylamine / CH₂Cl₂ / 14 h / 20 °C

6: 96 percent / hydrogen / palladium on activated charcoal / methanol / 18 h / 20 °C / 760 Torr

7: aq. HCl / 48 h / Heating

8: 95 percent / 4-(dimethylamino)pyridine; dicyclohexylcarbodiimide / pyridine / 24 h / 20 °C

9: 77 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.33 h

10: aq. phosphate buffer; pig liver esterase (EC 3.1.1.1); KOH / 336 h / 20 °C / pH 7.5

11: 73 percent / DMSO; dicyclohexylcarbodiimide; orthophosphoric acid

12: TsOH / toluene / 3 h / Heating

13: 31.0 mg / NaOMe / methanol / 0.5 h / 20 °C

14: 87 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 24 h

With pyridine; hydrogenchloride; dmap; potassium hydroxide; phosphate buffer; phosphoric acid; pig liver esterase (EC 3.1.1.1); hydrogen; sodium methylate; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; nickel; In tetrahydrofuran; pyridine; methanol; dichloromethane; toluene; 1: Acetylation / 2: Reduction / 3: Acetylation / 4: deacetalization / 5: Wittig olefination / 6: Catalytic hydrogenation / 7: Hydrolysis / 8: Cyclization / 9: Acetylation / 10: Hydrolysis / 11: Moffatt oxidation / 12: ketalization / 13: Zemplen deacetylation / 14: Esterification;

DOI:10.1021/jo990293i

Reference yield:

(1S,2R,3R)-2-Amino-2-[1,3]dioxan-2-ylmethyl-cyclohexane-1,3-diol → (-)-(6S,12S)-12-phenoxythionocarbonyloxy-7-aza-1,4-dioxadispiro[4,0,5,4]pentadecan-8-one (244154-16-3)

Guidance literature:

Multi-step reaction with 12 steps

1: 47.0 mg / pyridine / 1 h / Heating

2: aqueous acetic acid / 1 h / 20 °C / ultrasound

3: 144 mg / triethylamine / CH₂Cl₂ / 14 h / 20 °C

4: 96 percent / hydrogen / palladium on activated charcoal / methanol / 18 h / 20 °C / 760 Torr

5: aq. HCl / 48 h / Heating

6: 95 percent / 4-(dimethylamino)pyridine; dicyclohexylcarbodiimide / pyridine / 24 h / 20 °C

7: 77 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.33 h

8: aq. phosphate buffer; pig liver esterase (EC 3.1.1.1); KOH / 336 h / 20 °C / pH 7.5

9: 73 percent / DMSO; dicyclohexylcarbodiimide; orthophosphoric acid

10: TsOH / toluene / 3 h / Heating

11: 31.0 mg / NaOMe / methanol / 0.5 h / 20 °C

12: 87 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 24 h

With pyridine; hydrogenchloride; dmap; potassium hydroxide; phosphate buffer; phosphoric acid; pig liver esterase (EC 3.1.1.1); hydrogen; sodium methylate; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In pyridine; methanol; dichloromethane; toluene; 1: Acetylation / 2: deacetalization / 3: Wittig olefination / 4: Catalytic hydrogenation / 5: Hydrolysis / 6: Cyclization / 7: Acetylation / 8: Hydrolysis / 9: Moffatt oxidation / 10: ketalization / 11: Zemplen deacetylation / 12: Esterification;

DOI:10.1021/jo990293i

upstream raw materials:

phenylcarbonochloridothioate

(+)-(6S,12S)-12-hydroxy-7-aza-1,4-dioxadispiro[4,0,5,4]pentadecan-8-one

meso-(6r,7R,11S)-2-oxo-1-azaspiro[5,5]undecan-7,11-diol

4-((1R,2R,6S)-1-Amino-2,6-dihydroxy-cyclohexyl)-butyric acid