(2S,3R,1'S,2'R)-N-tert-butoxycarbonyl-3-benzyloxy-2-[2'-ethoxycarbonyl-1',2'-dihydroxyethyl]piperidine

Base Information

• Chemical Name: (2S,3R,1'S,2'R)-N-tert-butoxycarbonyl-3-benzyloxy-2-[2'-ethoxycarbonyl-1',2'-dihydroxyethyl]piperidine
• CAS No.: 849928-69-4
• Molecular Formula: C₂₂H₃₃NO₇
• Molecular Weight: 423.507
• Mol file: 849928-69-4.mol

Synonyms:(2S,3R,1'S,2'R)-N-tert-butoxycarbonyl-3-benzyloxy-2-[2'-ethoxycarbonyl-1',2'-dihydroxyethyl]piperidine

Chemical Property of (2S,3R,1'S,2'R)-N-tert-butoxycarbonyl-3-benzyloxy-2-[2'-ethoxycarbonyl-1',2'-dihydroxyethyl]piperidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,1'S,2'R)-N-tert-butoxycarbonyl-3-benzyloxy-2-[2'-ethoxycarbonyl-1',2'-dihydroxyethyl]piperidine

There total 8 articles about (2S,3R,1'S,2'R)-N-tert-butoxycarbonyl-3-benzyloxy-2-[2'-ethoxycarbonyl-1',2'-dihydroxyethyl]piperidine 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:

(2R,3R)-2,3-epoxy-4-pentenyl-N-allylcarbamate → (2S,3R,1'S,2'R)-N-tert-butoxycarbonyl-3-benzyloxy-2-[2'-ethoxycarbonyl-1',2'-dihydroxyethyl]piperidine (849928-69-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: NaN(TNS)2 / tetrahydrofuran / 23 °C

2.1: Grubbs's catalyst / CH₂Cl₂

3.1: 99 percent / H₂ / Pd/C / ethyl acetate / 1 h / 23 °C / 760 Torr

4.1: 97 percent / NaH / dimethylformamide / -20 - 23 °C

5.1: aq. NaOH / methanol; H₂O / 14 h / 100 °C

6.1: 0.082 g / aq. NaHCO₃ / ethyl acetate / 14 h / 23 °C

7.1: Dess-Martin periodinane / CH₂Cl₂ / 23 °C

8.1: LiCl; DBU / acetonitrile / 2 h / 23 °C

8.2: 46 mg / NMO; OsO₄ / acetone; H₂O; 2-methyl-propan-2-ol / 48 h / 23 °C

With sodium hydroxide; hydrogen; sodium hexamethyldisilazane; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; palladium on activated charcoal; Grubbs catalyst first generation; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 7.1: Dess-Martin oxidation;

DOI:10.1021/jo048172s

Reference yield:

(8R,8aS)-8-hydroxy-8,8a-dihydro-1H-oxazolo[3,4-a]pyridin-3(5H)-one (448896-88-6) → (2S,3R,1'S,2'R)-N-tert-butoxycarbonyl-3-benzyloxy-2-[2'-ethoxycarbonyl-1',2'-dihydroxyethyl]piperidine (849928-69-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 99 percent / H₂ / Pd/C / ethyl acetate / 1 h / 23 °C / 760 Torr

2.1: 97 percent / NaH / dimethylformamide / -20 - 23 °C

3.1: aq. NaOH / methanol; H₂O / 14 h / 100 °C

4.1: 0.082 g / aq. NaHCO₃ / ethyl acetate / 14 h / 23 °C

5.1: Dess-Martin periodinane / CH₂Cl₂ / 23 °C

6.1: LiCl; DBU / acetonitrile / 2 h / 23 °C

6.2: 46 mg / NMO; OsO₄ / acetone; H₂O; 2-methyl-propan-2-ol / 48 h / 23 °C

With sodium hydroxide; hydrogen; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; palladium on activated charcoal; In methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 5.1: Dess-Martin oxidation;

DOI:10.1021/jo048172s

Reference yield:

(4S)-4-[(1'R)-1'-hydroxy-2'-propenyl]-3-allyl-1,3-oxazolidin-2-one → (2S,3R,1'S,2'R)-N-tert-butoxycarbonyl-3-benzyloxy-2-[2'-ethoxycarbonyl-1',2'-dihydroxyethyl]piperidine (849928-69-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: Grubbs's catalyst / CH₂Cl₂

2.1: 99 percent / H₂ / Pd/C / ethyl acetate / 1 h / 23 °C / 760 Torr

3.1: 97 percent / NaH / dimethylformamide / -20 - 23 °C

4.1: aq. NaOH / methanol; H₂O / 14 h / 100 °C

5.1: 0.082 g / aq. NaHCO₃ / ethyl acetate / 14 h / 23 °C

6.1: Dess-Martin periodinane / CH₂Cl₂ / 23 °C

7.1: LiCl; DBU / acetonitrile / 2 h / 23 °C

7.2: 46 mg / NMO; OsO₄ / acetone; H₂O; 2-methyl-propan-2-ol / 48 h / 23 °C

With sodium hydroxide; hydrogen; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; palladium on activated charcoal; Grubbs catalyst first generation; In methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 6.1: Dess-Martin oxidation;

DOI:10.1021/jo048172s

upstream raw materials:

diethoxyphosphoryl-acetic acid ethyl ester

(2R,3R)-3-Benzyloxy-2-formyl-piperidine-1-carboxylic acid tert-butyl ester

(8R,8aS)-8-hydroxy-8,8a-dihydro-1H-oxazolo[3,4-a]pyridin-3(5H)-one

(8R,8aS)-8-hydroxyhexahydrooxazolo[3,4-a]pyridin-3-one

Downstream raw materials:

(1S,2R,8R,8aS)-8-benzyloxy-1,2-dihydroxyhexahydroindolizin-3-one