O-Deacetyl-N-(benzyloxycarbonyl)slaframine

Base Information

• Chemical Name: O-Deacetyl-N-(benzyloxycarbonyl)slaframine
• CAS No.: 153379-64-7
• Molecular Formula: C₁₆H₂₂N₂O₃
• Molecular Weight: 290.362
• Mol file: 153379-64-7.mol

Synonyms:O-Deacetyl-N-(benzyloxycarbonyl)slaframine

Chemical Property of O-Deacetyl-N-(benzyloxycarbonyl)slaframine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O-Deacetyl-N-(benzyloxycarbonyl)slaframine

There total 24 articles about O-Deacetyl-N-(benzyloxycarbonyl)slaframine 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: 87.0%

((1S,6S,8aS)-1-Methoxymethoxy-octahydro-indolizin-6-yl)-carbamic acid benzyl ester (153277-29-3) → O-Deacetyl-N-(benzyloxycarbonyl)slaframine (153379-64-7)

Guidance literature:

With methanol; acetyl chloride; at 65 ℃; for 0.333333h;

Reference yield:

N-benzyloxycarbonyl-L-serine methyl ester (1676-81-9) → O-Deacetyl-N-(benzyloxycarbonyl)slaframine (153379-64-7)

Guidance literature:

Multi-step reaction with 12 steps

1: 78 percent / DMAP, pyridine / CH₂Cl₂ / 16 h / -18 °C

2: 98 percent / NaH / dimethylformamide / 1.) 10 min, 2.) 20 deg C, 16 h

3: 97 percent / NaBH₄ / methanol / 5 h / 20 °C

4: 92 percent / DMAP, Et₃N / CH₂Cl₂ / 16 h / 20 °C

5: 87 percent / MCPBA / CH₂Cl₂ / 1.) ice-cooling, 0.5 h, 2.) 20 deg C, 2 h

6: 60 percent / BuLi / tetrahydrofuran; hexane / 1.) -78 deg C to 0 deg C, 1 h, 2.) -78 deg C to 0 deg C, 4 h

7: 97 percent / Na, KH₂PO₄ / methanol / 18 h / 0 - 20 °C

8: 78 percent / 2,4,6-triisopropylbenzenesulfonyl hydrazide, Et₃N / CH₂Cl₂ / 56 h / 20 °C

9: 92 percent / TBAF / tetrahydrofuran / 2 h / 0 - 20 °C

10: DMAP, Et₃N / CH₂Cl₂ / 16 h / -18 °C

11: TFA / CH₂Cl₂ / 0.5 h / 20 °C

12: 87 percent / AcCl, MeOH / 0.33 h / 65 °C

With pyridine; methanol; dmap; sodium tetrahydroborate; potassium dihydrogenphosphate; n-butyllithium; sodium amalgam; trisylhydrazine; tetrabutyl ammonium fluoride; sodium hydride; triethylamine; acetyl chloride; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

Methyl (2R,3S)-1-(tert-butoxycarbonyl)-3-hydroxypyrrolidine-2-carboxylate (130966-41-5) → O-Deacetyl-N-(benzyloxycarbonyl)slaframine (153379-64-7)

Guidance literature:

Multi-step reaction with 10 steps

1: 92 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 15 h / 20 °C

2: 71 percent / BF₃*Et₂O, diisobutylaluminium hydride / toluene / 1.) -78 deg C, 1 h, 2.) r.t., 4 h

3: 79 percent / TPAP, N-methylmorpholine N-oxide, molecular sieves / CH₂Cl₂; acetonitrile / 18 h / Ambient temperature

4: 60 percent / BuLi / tetrahydrofuran; hexane / 1.) -78 deg C to 0 deg C, 1 h, 2.) -78 deg C to 0 deg C, 4 h

5: 97 percent / Na, KH₂PO₄ / methanol / 18 h / 0 - 20 °C

6: 78 percent / 2,4,6-triisopropylbenzenesulfonyl hydrazide, Et₃N / CH₂Cl₂ / 56 h / 20 °C

7: 92 percent / TBAF / tetrahydrofuran / 2 h / 0 - 20 °C

8: DMAP, Et₃N / CH₂Cl₂ / 16 h / -18 °C

9: TFA / CH₂Cl₂ / 0.5 h / 20 °C

10: 87 percent / AcCl, MeOH / 0.33 h / 65 °C

With methanol; dmap; potassium dihydrogenphosphate; n-butyllithium; molecular sieve; tetrapropylammonium perruthennate; sodium amalgam; trisylhydrazine; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; acetyl chloride; trifluoroacetic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; acetonitrile;

upstream raw materials:

((1S,6S,8aS)-1-Methoxymethoxy-octahydro-indolizin-6-yl)-carbamic acid benzyl ester

N-benzyloxycarbonyl-L-serine methyl ester

Methyl 1-(tert-butoxycarbonyl)-3-oxopyrrolidine-2-carboxylate

Methyl (2R,3S)-1-(tert-butoxycarbonyl)-3-hydroxypyrrolidine-2-carboxylate

Downstream raw materials:

(1S,6S,8aS)-6-(benzyloxycarbonylamino)octahydroindolizin-1-yl acetate

(1S,6S,8aS)-1-acetoxy-6-aminooctahydroindolizidine

(-)-slaframine