(2R,3S)-3-Benzyloxy-2-[2-hydroxy-3-(4-oxo-4H-quinazolin-3-yl)-propyl]-piperidine-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: (2R,3S)-3-Benzyloxy-2-[2-hydroxy-3-(4-oxo-4H-quinazolin-3-yl)-propyl]-piperidine-1-carboxylic acid benzyl ester
• CAS No.: 304665-11-0
• Molecular Formula: C₃₁H₃₃N₃O₅
• Molecular Weight: 527.62
• Mol file: 304665-11-0.mol

Synonyms:(2R,3S)-3-Benzyloxy-2-[2-hydroxy-3-(4-oxo-4H-quinazolin-3-yl)-propyl]-piperidine-1-carboxylic acid benzyl ester

Chemical Property of (2R,3S)-3-Benzyloxy-2-[2-hydroxy-3-(4-oxo-4H-quinazolin-3-yl)-propyl]-piperidine-1-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-3-Benzyloxy-2-[2-hydroxy-3-(4-oxo-4H-quinazolin-3-yl)-propyl]-piperidine-1-carboxylic acid benzyl ester

There total 21 articles about (2R,3S)-3-Benzyloxy-2-[2-hydroxy-3-(4-oxo-4H-quinazolin-3-yl)-propyl]-piperidine-1-carboxylic acid benzyl 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:

(1S,5S,7R)-7-(tert-Butyl-dimethyl-silanyloxymethyl)-6,8-dioxa-bicyclo[3.2.1]oct-3-en-2-one (221015-46-9) → (2R,3S)-3-Benzyloxy-2-[2-hydroxy-3-(4-oxo-4H-quinazolin-3-yl)-propyl]-piperidine-1-carboxylic acid benzyl ester (304665-11-0)

Guidance literature:

Multi-step reaction with 22 steps

1: 90 percent / NaBH₄; CeCl₃ / methanol / 0 °C

2: H₂ / PtO₂

3: Et₃N

4: NaN₃ / dimethylformamide / Heating

5: LiAlH₄ / tetrahydrofuran

6: K₂CO₃

7: 90 percent / NaH / dimethylformamide

8: TBAF / tetrahydrofuran

9: Et₃N

10: LiI / tetrahydrofuran

11: Zn; AcOH / ethanol

12: 94 percent / NaBH₄ / ethanol

13: bis(tricyclohexylphosphine)benzylideneruthenium(IV)dichlorid

14: H₂ / PtO₂

15: Bu₃P; Py

16: NaH

17: H₂O₂ / H₂O

18: CaCO₃ / diphenyl ether / Heating

19: OsO₄; NMO / H₂O; tetrahydrofuran

20: Py

21: K₂CO₃ / methanol

22: 61 percent / KOH / methanol

With pyridine; potassium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; lithium aluminium tetrahydride; Grubbs catalyst first generation; sodium azide; N-methyl-2-indolinone; cerium(III) chloride; tributylphosphine; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; sodium hydride; potassium carbonate; acetic acid; triethylamine; calcium carbonate; lithium iodide; zinc; platinum(IV) oxide; In tetrahydrofuran; methanol; diphenylether; ethanol; water; N,N-dimethyl-formamide; 1: Reduction / 2: Catalytic hydrogenation / 3: Substitution / 4: Substitution / 5: Reduction / 6: Substitution / 7: Substitution / 8: desilylation / 9: Substitution / 10: Substitution / 11: Reduction / 12: Reduction / 13: Cyclization / 14: Catalytic hydrogenation / 15: Substitution / 16: Substitution / 17: Oxidation / 18: Elimination / 19: hydroxylation / 20: Tosylation / 21: Cyclization / 22: Ring cleavage;

DOI:10.1021/ol006384f

Reference yield:

(1R,2S,5S,7R)-7-(tert-Butyl-dimethyl-silanyloxymethyl)-6,8-dioxa-bicyclo[3.2.1]oct-3-en-2-ol (221015-49-2) → (2R,3S)-3-Benzyloxy-2-[2-hydroxy-3-(4-oxo-4H-quinazolin-3-yl)-propyl]-piperidine-1-carboxylic acid benzyl ester (304665-11-0)

Guidance literature:

Multi-step reaction with 21 steps

1: H₂ / PtO₂

2: Et₃N

3: NaN₃ / dimethylformamide / Heating

4: LiAlH₄ / tetrahydrofuran

5: K₂CO₃

6: 90 percent / NaH / dimethylformamide

7: TBAF / tetrahydrofuran

8: Et₃N

9: LiI / tetrahydrofuran

10: Zn; AcOH / ethanol

11: 94 percent / NaBH₄ / ethanol

12: bis(tricyclohexylphosphine)benzylideneruthenium(IV)dichlorid

13: H₂ / PtO₂

14: Bu₃P; Py

15: NaH

16: H₂O₂ / H₂O

17: CaCO₃ / diphenyl ether / Heating

18: OsO₄; NMO / H₂O; tetrahydrofuran

19: Py

20: K₂CO₃ / methanol

21: 61 percent / KOH / methanol

With pyridine; potassium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; lithium aluminium tetrahydride; Grubbs catalyst first generation; sodium azide; N-methyl-2-indolinone; tributylphosphine; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; sodium hydride; potassium carbonate; acetic acid; triethylamine; calcium carbonate; lithium iodide; zinc; platinum(IV) oxide; In tetrahydrofuran; methanol; diphenylether; ethanol; water; N,N-dimethyl-formamide; 1: Catalytic hydrogenation / 2: Substitution / 3: Substitution / 4: Reduction / 5: Substitution / 6: Substitution / 7: desilylation / 8: Substitution / 9: Substitution / 10: Reduction / 11: Reduction / 12: Cyclization / 13: Catalytic hydrogenation / 14: Substitution / 15: Substitution / 16: Oxidation / 17: Elimination / 18: hydroxylation / 19: Tosylation / 20: Cyclization / 21: Ring cleavage;

DOI:10.1021/ol006384f

Reference yield:

(1R,2S,5S,7R)-7-(tert-Butyl-dimethyl-silanyloxymethyl)-6,8-dioxa-bicyclo[3.2.1]octan-2-ol (344569-32-0) → (2R,3S)-3-Benzyloxy-2-[2-hydroxy-3-(4-oxo-4H-quinazolin-3-yl)-propyl]-piperidine-1-carboxylic acid benzyl ester (304665-11-0)

Guidance literature:

Multi-step reaction with 20 steps

1: Et₃N

2: NaN₃ / dimethylformamide / Heating

3: LiAlH₄ / tetrahydrofuran

4: K₂CO₃

5: 90 percent / NaH / dimethylformamide

6: TBAF / tetrahydrofuran

7: Et₃N

8: LiI / tetrahydrofuran

9: Zn; AcOH / ethanol

10: 94 percent / NaBH₄ / ethanol

11: bis(tricyclohexylphosphine)benzylideneruthenium(IV)dichlorid

12: H₂ / PtO₂

13: Bu₃P; Py

14: NaH

15: H₂O₂ / H₂O

16: CaCO₃ / diphenyl ether / Heating

17: OsO₄; NMO / H₂O; tetrahydrofuran

18: Py

19: K₂CO₃ / methanol

20: 61 percent / KOH / methanol

With pyridine; potassium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; lithium aluminium tetrahydride; Grubbs catalyst first generation; sodium azide; N-methyl-2-indolinone; tributylphosphine; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; sodium hydride; potassium carbonate; acetic acid; triethylamine; calcium carbonate; lithium iodide; zinc; platinum(IV) oxide; In tetrahydrofuran; methanol; diphenylether; ethanol; water; N,N-dimethyl-formamide; 1: Substitution / 2: Substitution / 3: Reduction / 4: Substitution / 5: Substitution / 6: desilylation / 7: Substitution / 8: Substitution / 9: Reduction / 10: Reduction / 11: Cyclization / 12: Catalytic hydrogenation / 13: Substitution / 14: Substitution / 15: Oxidation / 16: Elimination / 17: hydroxylation / 18: Tosylation / 19: Cyclization / 20: Ring cleavage;

DOI:10.1021/ol006384f

upstream raw materials:

(1S,5S,7R)-7-(tert-Butyl-dimethyl-silanyloxymethyl)-6,8-dioxa-bicyclo[3.2.1]oct-3-en-2-one

(1R,2S,5S,7R)-7-(tert-Butyl-dimethyl-silanyloxymethyl)-6,8-dioxa-bicyclo[3.2.1]oct-3-en-2-ol

(1R,2S,5S,7R)-7-(tert-Butyl-dimethyl-silanyloxymethyl)-6,8-dioxa-bicyclo[3.2.1]octan-2-ol

((1R,2R,5R,7R)-2-Azido-6,8-dioxa-bicyclo[3.2.1]oct-7-ylmethoxy)-tert-butyl-dimethyl-silane

Downstream raw materials:

(2R,3S)-3-benzyloxy-2-[2-oxo-3-(4-oxoquinazolin-3(4H)-yl)propyl]piperidine-1-carboxylic acid benzyl ester

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