(6R,7S,8R,8aR)-6,7,8-tris(benzyloxy)-8a-methyl-5,6,7,8-tetrahydroindolizin-3-one

Base Information

• Chemical Name: (6R,7S,8R,8aR)-6,7,8-tris(benzyloxy)-8a-methyl-5,6,7,8-tetrahydroindolizin-3-one
• CAS No.: 616234-33-4
• Molecular Formula: C₃₀H₃₁NO₄
• Molecular Weight: 469.58
• Mol file: 616234-33-4.mol

Synonyms:(6R,7S,8R,8aR)-6,7,8-tris(benzyloxy)-8a-methyl-5,6,7,8-tetrahydroindolizin-3-one

Chemical Property of (6R,7S,8R,8aR)-6,7,8-tris(benzyloxy)-8a-methyl-5,6,7,8-tetrahydroindolizin-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6R,7S,8R,8aR)-6,7,8-tris(benzyloxy)-8a-methyl-5,6,7,8-tetrahydroindolizin-3-one

There total 9 articles about (6R,7S,8R,8aR)-6,7,8-tris(benzyloxy)-8a-methyl-5,6,7,8-tetrahydroindolizin-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: 74.0%

(2R,3R,4S,5R)-3,4,5-tris(benzyloxy)-1-[2'-(diethoxyphosphoryl)acetyl]-2-hydroxymethyl-2-methylpiperidine (616234-32-3) → (6R,7S,8R,8aR)-6,7,8-tris(benzyloxy)-8a-methyl-5,6,7,8-tetrahydroindolizin-3-one (616234-33-4)

Guidance literature:

(2R,3R,4S,5R)-3,4,5-tris(benzyloxy)-1-[2'-(diethoxyphosphoryl)acetyl]-2-hydroxymethyl-2-methylpiperidine; With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 10h;

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 20 ℃; for 72h;

DOI:10.1002/ejoc.200300079

Reference yield:

(2S,3R)-3-((4R,5R)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-2-methyl-2-(toluene-4-sulfonylamino)-propionic acid tert-butyl ester → (6R,7S,8R,8aR)-6,7,8-tris(benzyloxy)-8a-methyl-5,6,7,8-tetrahydroindolizin-3-one (616234-33-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 100 percent / hydrogen / Pd/C / methanol / 20 °C / 2250.18 Torr

2.1: 72 percent / DEAD; PPh₃ / tetrahydrofuran / 20 °C

3.1: 100 percent / Dowex 50WX₈ / methanol; H₂O / 10 h / 20 °C

4.1: 99 percent / tetra-n-butylammonium iodide; NaH / dimethylformamide / 0 - 20 °C

5.1: 98 percent / LiAlH₄ / tetrahydrofuran / 0 - 20 °C

6.1: 99 percent / sodium naphthalide / 1,2-dimethoxy-ethane / -60 °C

7.1: 88 percent / O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium BF₄; NEt₃ / CH₂Cl₂ / -20 - 20 °C

8.1: Dess-Martin periodinane / CH₂Cl₂ / 10 h / 20 °C

8.2: 74 percent / DBU / tetrahydrofuran / 72 h / 20 °C

With lithium aluminium tetrahydride; dowex 50Wx₈; hydrogen; tetra-(n-butyl)ammonium iodide; sodium naphthalenide; sodium hydride; Dess-Martin periodane; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide; 2.1: Mitsunobu cyclization;

DOI:10.1002/ejoc.200300079

Reference yield:

benzyl bromide (100-39-0) → (6R,7S,8R,8aR)-6,7,8-tris(benzyloxy)-8a-methyl-5,6,7,8-tetrahydroindolizin-3-one (616234-33-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 99 percent / tetra-n-butylammonium iodide; NaH / dimethylformamide / 0 - 20 °C

2.1: 98 percent / LiAlH₄ / tetrahydrofuran / 0 - 20 °C

3.1: 99 percent / sodium naphthalide / 1,2-dimethoxy-ethane / -60 °C

4.1: 88 percent / O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium BF₄; NEt₃ / CH₂Cl₂ / -20 - 20 °C

5.1: Dess-Martin periodinane / CH₂Cl₂ / 10 h / 20 °C

5.2: 74 percent / DBU / tetrahydrofuran / 72 h / 20 °C

With lithium aluminium tetrahydride; tetra-(n-butyl)ammonium iodide; sodium naphthalenide; sodium hydride; Dess-Martin periodane; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.200300079

upstream raw materials:

(2R,3R,4S,5R)-3,4,5-tris(benzyloxy)-1-[2'-(diethoxyphosphoryl)acetyl]-2-hydroxymethyl-2-methylpiperidine

benzyl bromide

tert-butyl (2S,3R,4S,5R)-3,4,5-trihydroxy-2-methyl-1-(p-toluenesulfonyl)piperidine-2-carboxylate

(3aR,6S,7R,7aR)-7-Hydroxy-2,2,6-trimethyl-5-(toluene-4-sulfonyl)-hexahydro-[1,3]dioxolo[4,5-c]pyridine-6-carboxylic acid tert-butyl ester