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

Base Information

• Chemical Name: (1S,2R,8R,8aS)-8-benzyloxy-1,2-dihydroxyhexahydroindolizin-3-one
• CAS No.: 849928-71-8
• Molecular Formula: C₁₅H₁₉NO₄
• Molecular Weight: 277.32
• Mol file: 849928-71-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about (1S,2R,8R,8aS)-8-benzyloxy-1,2-dihydroxyhexahydroindolizin-3-one 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: 84.0%

(2S,3R,1'S,2'R)-N-tert-butoxycarbonyl-3-benzyloxy-2-[2'-ethoxycarbonyl-1',2'-dihydroxyethyl]piperidine (849928-69-4) → (1S,2R,8R,8aS)-8-benzyloxy-1,2-dihydroxyhexahydroindolizin-3-one (849928-71-8)

Guidance literature:

(2S,3R,1'S,2'R)-N-tert-butoxycarbonyl-3-benzyloxy-2-[2'-ethoxycarbonyl-1',2'-dihydroxyethyl]piperidine; With hydrogenchloride; In diethyl ether; at 23 ℃; for 4h;

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; for 14h; Heating;

DOI:10.1021/jo048172s

Reference yield:

(2R,3R)-2,3-epoxy-4-pentenyl-N-allylcarbamate → (1S,2R,8R,8aS)-8-benzyloxy-1,2-dihydroxyhexahydroindolizin-3-one (849928-71-8)

Guidance literature:

Multi-step reaction with 9 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

9.1: HCl / diethyl ether / 4 h / 23 °C

9.2: 84 percent / DIPEA / tetrahydrofuran / 14 h / Heating

With hydrogenchloride; 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; diethyl ether; 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) → (1S,2R,8R,8aS)-8-benzyloxy-1,2-dihydroxyhexahydroindolizin-3-one (849928-71-8)

Guidance literature:

Multi-step reaction with 7 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

7.1: HCl / diethyl ether / 4 h / 23 °C

7.2: 84 percent / DIPEA / tetrahydrofuran / 14 h / Heating

With hydrogenchloride; 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; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 5.1: Dess-Martin oxidation;

DOI:10.1021/jo048172s

upstream raw materials:

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

(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

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