2-Pyridinecarboxylic acid, 4-[(1S)-1-formyl-1-hydroxypropyl]-6-methoxy-5-[(phenylmethoxy)methyl]- , propyl ester

Base Information

• Chemical Name: 2-Pyridinecarboxylic acid, 4-[(1S)-1-formyl-1-hydroxypropyl]-6-methoxy-5-[(phenylmethoxy)methyl]- , propyl ester
• CAS No.: 183433-96-7
• Molecular Formula: C22H27NO6
• Molecular Weight: 401.459
• Mol file: 183433-96-7.mol

Synonyms:

Chemical Property of 2-Pyridinecarboxylic acid, 4-[(1S)-1-formyl-1-hydroxypropyl]-6-methoxy-5-[(phenylmethoxy)methyl]- , propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Pyridinecarboxylic acid, 4-[(1S)-1-formyl-1-hydroxypropyl]-6-methoxy-5-[(phenylmethoxy)methyl]- , propyl ester

There total 12 articles about 2-Pyridinecarboxylic acid, 4-[(1S)-1-formyl-1-hydroxypropyl]-6-methoxy-5-[(phenylmethoxy)methyl]- , propyl 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: 100.0%

5-Benzyloxymethyl-4-((S)-1-hydroxy-1-hydroxymethyl-propyl)-6-methoxy-pyridine-2-carboxylic acid propyl ester (183433-75-2) → 5-Benzyloxymethyl-4-((S)-1-formyl-1-hydroxy-propyl)-6-methoxy-pyridine-2-carboxylic acid propyl ester (183433-96-7)

Guidance literature:

With sodium hypochlorite; 4-acetoxy-2,2,6,6-tetramethylpiperidine-1-oxyl; sodium hydrogencarbonate; potassium bromide; In dichloromethane; water; for 0.666667h;

DOI:10.1021/jo970173f

Reference yield:

2,6-dichloropyridine-4-carboxylic acid (5398-44-7) → 5-Benzyloxymethyl-4-((S)-1-formyl-1-hydroxy-propyl)-6-methoxy-pyridine-2-carboxylic acid propyl ester (183433-96-7)

Guidance literature:

Multi-step reaction with 11 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

With palladium diacetate; 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; sodium hydrogencarbonate; potassium carbonate; potassium bromide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1021/jo970173f

Reference yield:

citrazinic acid (99-11-6) → 5-Benzyloxymethyl-4-((S)-1-formyl-1-hydroxy-propyl)-6-methoxy-pyridine-2-carboxylic acid propyl ester (183433-96-7)

Guidance literature:

Multi-step reaction with 12 steps

1: 78 percent / POPCl₃, Me₄NCl / 2 h / 130 - 142 °C

2: 84 percent / tetrahydrofuran / 1 h / 0 °C

3: 100 percent / TMSCl / 12 h / Ambient temperature

4: 89 percent / methanol / 20 h / Heating

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

6: 71 percent / NaBH₄, n-Bu₄NCl / H₂O / 18 h

7: 99.3 percent / t-BuOK / tetrahydrofuran / 1 h / 20 - 30 °C

8: 89 percent / Pd(OAc)2, K₂CO₃, DPP / dimethylformamide / 16 h / 90 °C / 775.7 Torr

10: 92 percent / OsO₄, Me₃NO*2H₂O / 2-methyl-propan-2-ol / 24 h / 40 °C

11: 76 percent / PS-30 catalyst / various solvent(s) / 48 h

12: 100 percent / NaOCl, 4-acetoxy-TEMPO, KBr, NaHCO₃ / CH₂Cl₂; H₂O / 0.67 h

With palladium diacetate; sodium hypochlorite; sodium tetrahydroborate; osmium(VIII) oxide; n-butyllithium; chloro-trimethyl-silane; 4-acetoxy-2,2,6,6-tetramethylpiperidine-1-oxyl; trimethylamine-N-oxide; POPCl₃; PS-30 catalyst; parathion; potassium tert-butylate; tetrabutyl-ammonium chloride; tetramethlyammonium chloride; sodium hydrogencarbonate; potassium carbonate; potassium bromide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1021/jo970173f

upstream raw materials:

5-Benzyloxymethyl-4-((S)-1-hydroxy-1-hydroxymethyl-propyl)-6-methoxy-pyridine-2-carboxylic acid propyl ester

citrazinic acid

2,6-dichloropyridine-4-carboxylic acid

1-(2,6-dichloropyridin-4-yl)propan-1-one

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

propyl (S)-4-ethyl-3,4,7,8-tetrahydro-4-hydroxy-3,8-dioxo-1H-pyrano[3,4-c] pyridine-6-carboxylate

Refernces