(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

Base Information

• Chemical Name: (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
• CAS No.: 196094-23-2
• Molecular Formula: C₄₀H₅₇NO₇Si
• Molecular Weight: 691.981

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 14 articles about (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 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: 95.0%

{(1R,2R,3S,4S)-2,3,4-Tris-benzyloxy-1-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-5,6-dihydroxy-hexyl}-carbamic acid tert-butyl ester (196094-22-1) → (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 (196094-23-2)

Guidance literature:

With sodium periodate; In diethyl ether; water;

DOI:10.1055/s-1997-962

Reference yield:

(3S,4R,5R)-5-(3-Benzyloxy-propyl)-1-(4-methoxy-benzyl)-3,4-bis-triisopropylsilanyloxy-pyrrolidin-2-one (196094-12-9) → (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 (196094-23-2)

Guidance literature:

Multi-step reaction with 13 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

With 1H-imidazole; methanol; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; formic acid; N-methyl-2-indolinone; cerium(III) chloride; ammonium cerium(IV) nitrate; 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 → (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 (196094-23-2)

Guidance literature:

Multi-step reaction with 14 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

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

upstream raw materials:

{(1R,2R,3S,4S)-2,3,4-Tris-benzyloxy-1-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-5,6-dihydroxy-hexyl}-carbamic acid tert-butyl ester

(3S,4R,5R)-3,4-Bis-benzyloxy-5-(3-hydroxy-propyl)-pyrrolidin-2-one

(3S,4R,5R)-3,4-Dihydroxy-1-(4-methoxy-benzyl)-5-[3-(tetrahydro-pyran-2-yloxy)-propyl]-pyrrolidin-2-one

(3S,4R,5R)-3,4-Bis-benzyloxy-5-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-pyrrolidin-2-one

Downstream raw materials:

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

1-deoxy-castanospermine

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

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