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

Base Information

Chemical Name:3-((2R,3R,4R,5S)-3,4,5-Tris-benzyloxy-piperidin-2-yl)-propan-1-ol
CAS No.:133521-24-1
Molecular Formula:C₂₉H₃₅NO₄
Molecular Weight:461.601
Hs Code.:

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

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Chemical Property of 3-((2R,3R,4R,5S)-3,4,5-Tris-benzyloxy-piperidin-2-yl)-propan-1-ol

Chemical Property:

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Technology Process of 3-((2R,3R,4R,5S)-3,4,5-Tris-benzyloxy-piperidin-2-yl)-propan-1-ol

There total 15 articles about 3-((2R,3R,4R,5S)-3,4,5-Tris-benzyloxy-piperidin-2-yl)-propan-1-ol 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%

: 196094-23-2
(2R,3R,4S,5R)-3,4,5-Tris-benzyloxy-2-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-6-hydroxy-piperidine-1-carboxylic acid tert-butyl ester

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

Guidance literature:: With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃;
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

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

Guidance literature:: Multi-step reaction with 14 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

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; 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

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

Guidance literature:: Multi-step reaction with 15 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

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; 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