(2R,3R,4R,5S)-3,4,5-Tris-benzyloxy-2-(3-hydroxy-propyl)-piperidine-1-carboxylic acid benzyl ester

Base Information

Chemical Name:(2R,3R,4R,5S)-3,4,5-Tris-benzyloxy-2-(3-hydroxy-propyl)-piperidine-1-carboxylic acid benzyl ester
CAS No.:196094-26-5
Molecular Formula:C₃₇H₄₁NO₆
Molecular Weight:595.736
Hs Code.:

Synonyms:(2R,3R,4R,5S)-3,4,5-Tris-benzyloxy-2-(3-hydroxy-propyl)-piperidine-1-carboxylic acid benzyl ester

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Chemical Property of (2R,3R,4R,5S)-3,4,5-Tris-benzyloxy-2-(3-hydroxy-propyl)-piperidine-1-carboxylic acid benzyl ester

Chemical Property:

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Technology Process of (2R,3R,4R,5S)-3,4,5-Tris-benzyloxy-2-(3-hydroxy-propyl)-piperidine-1-carboxylic acid benzyl ester

There total 16 articles about (2R,3R,4R,5S)-3,4,5-Tris-benzyloxy-2-(3-hydroxy-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: 99.0%

: 133521-24-1
3-((2R,3R,4R,5S)-3,4,5-Tris-benzyloxy-piperidin-2-yl)-propan-1-ol

: 501-53-1,94274-21-2
benzyl chloroformate

: 196094-26-5
(2R,3R,4R,5S)-3,4,5-Tris-benzyloxy-2-(3-hydroxy-propyl)-piperidine-1-carboxylic acid benzyl ester

Guidance literature:: With sodium hydrogencarbonate; In dichloromethane;
DOI:10.1055/s-1997-962

Reference yield:

: 196094-12-9
(3S,4R,5R)-5-(3-Benzyloxy-propyl)-1-(4-methoxy-benzyl)-3,4-bis-triisopropylsilanyloxy-pyrrolidin-2-one

: 196094-26-5
(2R,3R,4R,5S)-3,4,5-Tris-benzyloxy-2-(3-hydroxy-propyl)-piperidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 15 steps

1: 88 percent / HCOOH / Pd(black) / methanol

2: 97 percent / p-TsOH / methanol; CH₂Cl₂

3: Bu₄NF / CH₂Cl₂

4: 99 percent / Ag₂O / ethyl acetate

5: p-TsOH, MeOH

6: 81 percent / CAN / H₂O; acetonitrile

7: 72 percent / imidazole, DMAP / dimethylformamide

8: Et₃N, DMAP / CH₂Cl₂

9: tetrahydrofuran / -78 °C

10: NaBH₄, CeCl₃ / methanol / -18 °C

11: 87 percent / Ag₂O / ethyl acetate

12: 88 percent / OsO₄, NMO / H₂O; acetone

13: 95 percent / NaIO₄ / diethyl ether; H₂O

14: 99 percent / Et₃SiH, BF₃*Et₂O / CH₂Cl₂ / 0 °C

15: 99 percent / NaHCO₃ / CH₂Cl₂

With 1H-imidazole; methanol; triethylsilane; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; formic acid; N-methyl-2-indolinone; cerium(III) chloride; ammonium cerium(IV) nitrate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; silver(l) oxide; palladium; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile;
DOI:10.1055/s-1997-962

Reference yield:

: (3S,4S)-5-(3-Benzyloxy-propyl)-5-hydroxy-1-(4-methoxy-benzyl)-3,4-bis-triisopropylsilanyloxy-pyrrolidin-2-one

: 196094-26-5
(2R,3R,4R,5S)-3,4,5-Tris-benzyloxy-2-(3-hydroxy-propyl)-piperidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 16 steps

1: Et₃SiH, BF₃*Et₂O / CH₂Cl₂ / -78 °C

2: 88 percent / HCOOH / Pd(black) / methanol

3: 97 percent / p-TsOH / methanol; CH₂Cl₂

4: Bu₄NF / CH₂Cl₂

5: 99 percent / Ag₂O / ethyl acetate

6: p-TsOH, MeOH

7: 81 percent / CAN / H₂O; acetonitrile

8: 72 percent / imidazole, DMAP / dimethylformamide

9: Et₃N, DMAP / CH₂Cl₂

10: tetrahydrofuran / -78 °C

11: NaBH₄, CeCl₃ / methanol / -18 °C

12: 87 percent / Ag₂O / ethyl acetate

13: 88 percent / OsO₄, NMO / H₂O; acetone

14: 95 percent / NaIO₄ / diethyl ether; H₂O

15: 99 percent / Et₃SiH, BF₃*Et₂O / CH₂Cl₂ / 0 °C

16: 99 percent / NaHCO₃ / CH₂Cl₂

With 1H-imidazole; methanol; triethylsilane; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; formic acid; N-methyl-2-indolinone; cerium(III) chloride; ammonium cerium(IV) nitrate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; silver(l) oxide; palladium; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile;
DOI:10.1055/s-1997-962