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

Base Information

Chemical Name:5-Benzyloxymethyl-4-((S)-1-hydroxy-1-hydroxymethyl-propyl)-6-methoxy-pyridine-2-carboxylic acid propyl ester
CAS No.:183433-75-2
Molecular Formula:C₂₂H₂₉NO₆
Molecular Weight:403.475
Hs Code.:

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

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

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

There total 13 articles about 5-Benzyloxymethyl-4-((S)-1-hydroxy-1-hydroxymethyl-propyl)-6-methoxy-pyridine-2-carboxylic acid 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: 76.0%

: 108-22-5
Isopropenyl acetate

: 183433-74-1
5-Benzyloxymethyl-4-(1-hydroxy-1-hydroxymethyl-propyl)-6-methoxy-pyridine-2-carboxylic acid propyl ester

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

: 185135-84-6
4-((R)-1-Acetoxymethyl-1-hydroxy-propyl)-5-benzyloxymethyl-6-methoxy-pyridine-2-carboxylic acid propyl ester

Guidance literature:: With PS-30 catalyst; In various solvent(s); for 48h;
DOI:10.1021/jo970173f

Reference yield:

: 5398-44-7
2,6-dichloropyridine-4-carboxylic acid

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

Guidance literature:: Multi-step reaction with 10 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

With palladium diacetate; sodium tetrahydroborate; osmium(VIII) oxide; n-butyllithium; chloro-trimethyl-silane; trimethylamine-N-oxide; PS-30 catalyst; parathion; potassium tert-butylate; tetrabutyl-ammonium chloride; potassium carbonate; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/jo970173f

Reference yield:

: 99-11-6
citrazinic acid

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

Guidance literature:: Multi-step reaction with 11 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

With palladium diacetate; sodium tetrahydroborate; osmium(VIII) oxide; n-butyllithium; chloro-trimethyl-silane; trimethylamine-N-oxide; POPCl₃; PS-30 catalyst; parathion; potassium tert-butylate; tetrabutyl-ammonium chloride; tetramethlyammonium chloride; potassium carbonate; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/jo970173f