(S)-4-Ethyl-4,6-dihydroxy-3,10-dioxo-3,4,8,10-tetrahydro-1H-pyrano[3,4-f]indolizine-7-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (S)-4-Ethyl-4,6-dihydroxy-3,10-dioxo-3,4,8,10-tetrahydro-1H-pyrano[3,4-f]indolizine-7-carboxylic acid tert-butyl ester
• CAS No.: 183434-04-0
• Molecular Formula: C18H21NO7
• Molecular Weight: 363.367
• Mol file: 183434-04-0.mol

Synonyms:

Chemical Property of (S)-4-Ethyl-4,6-dihydroxy-3,10-dioxo-3,4,8,10-tetrahydro-1H-pyrano[3,4-f]indolizine-7-carboxylic acid tert-butyl ester

Chemical Property:

• PSA: 115.06000
• LogP: 1.12710

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-4-Ethyl-4,6-dihydroxy-3,10-dioxo-3,4,8,10-tetrahydro-1H-pyrano[3,4-f]indolizine-7-carboxylic acid tert-butyl ester

There total 1 articles about (S)-4-Ethyl-4,6-dihydroxy-3,10-dioxo-3,4,8,10-tetrahydro-1H-pyrano[3,4-f]indolizine-7-carboxylic acid tert-butyl ester 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:

2,6-dichloropyridine-4-carboxylic acid (5398-44-7) → 1,1-dimethylethyl (S)-4-ethyl-3,4,8,10-tetrahydro-4,6-dihydroxy-3,10-dioxo-1H-pyrano[3,4 - f] indolidin-7-carboxylate (183434-04-0)

Guidance literature:

Multi-step reaction with 15 steps

1: 84 percent / tetrahydrofuran / 1 h / 0 °C

2: 100 percent / TMSCl / 12 h / Ambient temperature

3: 89 percent / methanol / 20 h / Heating

4: 1.) n-BuLi / 1.) heptane, hexane, 0 deg C, 30 min, 2.) hexane, heptane, -30 deg C - 0 deg C, 1 h

5: 71 percent / NaBH₄, n-Bu₄NCl / H₂O / 18 h

6: 99.3 percent / t-BuOK / tetrahydrofuran / 1 h / 20 - 30 °C

7: 89 percent / Pd(OAc)2, K₂CO₃, DPP / dimethylformamide / 16 h / 90 °C / 775.7 Torr

9: 92 percent / OsO₄, Me₃NO*2H₂O / 2-methyl-propan-2-ol / 24 h / 40 °C

10: 76 percent / PS-30 catalyst / various solvent(s) / 48 h

11: 100 percent / NaOCl, 4-acetoxy-TEMPO, KBr, NaHCO₃ / CH₂Cl₂; H₂O / 0.67 h

12: 96 percent / H₂ / Pd/C / methanol / 96 h / 775.7 Torr / Ambient temperature; other catalyst, reaction time, temperature

13: 99 percent / TEMPO, KBr, NaHCO₃, NaOCl / CH₂Cl₂; H₂O / 0.5 h

14: 89 percent / TMSCl, NaI / acetonitrile / 6 h / 0 - 20 °C

15: 74 percent / Cs₂CO₃ / dimethylsulfoxide / 21 h / 47 - 50 °C

With palladium diacetate; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium tetrahydroborate; osmium(VIII) oxide; n-butyllithium; chloro-trimethyl-silane; 4-acetoxy-2,2,6,6-tetramethylpiperidine-1-oxyl; trimethylamine-N-oxide; PS-30 catalyst; parathion; potassium tert-butylate; tetrabutyl-ammonium chloride; hydrogen; sodium hydrogencarbonate; potassium carbonate; caesium carbonate; sodium iodide; potassium bromide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;

DOI:10.1021/jo970173f

Reference yield: 93.4%

1,1-dimethylethyl (S)-4-ethyl-3,4,8,10-tetrahydro-4,6-dihydroxy-3,10-dioxo-1H-pyrano[3,4 - f] indolidin-7-carboxylate (183434-04-0) → (4S)-4-ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione (110351-94-5)

Guidance literature:

In toluene; trifluoroacetic acid; at 110 ℃; for 2h;

DOI:10.1021/jo970173f

Reference yield:

1,1-dimethylethyl (S)-4-ethyl-3,4,8,10-tetrahydro-4,6-dihydroxy-3,10-dioxo-1H-pyrano[3,4 - f] indolidin-7-carboxylate (183434-04-0) → irinotecan (97682-44-5,130144-33-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 93.4 percent / trifluoroacetic acid; toluene / 2 h / 110 °C

2: p-TSA*H₂O / toluene; acetic acid / 18 h / 95 - 100 °C

3: pyridine / 2 h / 20 - 25 °C

With toluene-4-sulfonic acid; In pyridine; acetic acid; toluene; trifluoroacetic acid;

DOI:10.1021/jo970173f

upstream raw materials:

2,6-dichloropyridine-4-carboxylic acid

Downstream raw materials:

(4S)-4-ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione

7-ethyl-10-hydroxycamptothecin

irinotecan

Refernces