(1'S,3'R,4'R,5'R,7'R)-N₂-benzoyl-1-{4'-acetoxy-1'-phenyl-3'-(t-butyldiphenylsilyloxymethyl)-2',6'-dioxabicyclo[3.3.0]oct-7'-yl}-4-methyl-3-pyrazolin-5-one

Base Information

• Chemical Name: (1'S,3'R,4'R,5'R,7'R)-N₂-benzoyl-1-{4'-acetoxy-1'-phenyl-3'-(t-butyldiphenylsilyloxymethyl)-2',6'-dioxabicyclo[3.3.0]oct-7'-yl}-4-methyl-3-pyrazolin-5-one
• CAS No.: 1195199-17-7
• Molecular Formula: C₄₂H₄₄N₂O₇Si
• Molecular Weight: 716.906

Synonyms:(1'S,3'R,4'R,5'R,7'R)-N₂-benzoyl-1-{4'-acetoxy-1'-phenyl-3'-(t-butyldiphenylsilyloxymethyl)-2',6'-dioxabicyclo[3.3.0]oct-7'-yl}-4-methyl-3-pyrazolin-5-one

Chemical Property of (1'S,3'R,4'R,5'R,7'R)-N₂-benzoyl-1-{4'-acetoxy-1'-phenyl-3'-(t-butyldiphenylsilyloxymethyl)-2',6'-dioxabicyclo[3.3.0]oct-7'-yl}-4-methyl-3-pyrazolin-5-one

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Technology Process of (1'S,3'R,4'R,5'R,7'R)-N₂-benzoyl-1-{4'-acetoxy-1'-phenyl-3'-(t-butyldiphenylsilyloxymethyl)-2',6'-dioxabicyclo[3.3.0]oct-7'-yl}-4-methyl-3-pyrazolin-5-one

There total 1 articles about (1'S,3'R,4'R,5'R,7'R)-N₂-benzoyl-1-{4'-acetoxy-1'-phenyl-3'-(t-butyldiphenylsilyloxymethyl)-2',6'-dioxabicyclo[3.3.0]oct-7'-yl}-4-methyl-3-pyrazolin-5-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: 13.0%

4-methyl-1,2-dihydro-pyrazol-3-one (3947-61-3,145092-11-1) + benzoyl chloride (98-88-4) + (1R,3R,4R,5R,7RS)-1-phenyl-3-(tert-butyldiphenylsilyloxymethyl)-4,7-diacetoxy-2,6-dioxabicylco[3.3.0]octane (389633-40-3) → (1'S,3'R,4'R,5'R,7'R)-N1-benzoyl-2-{4'-acetoxy-1'-phenyl-3'-(t-butyldiphenylsilyloxymethyl)-2',6'-dioxabicyclo[3.3.0]oct-7'-yl}-4-methyl-3-pyrazolin-5-one (1195199-11-1) + (1'S,3'R,4'R,5'R,7'S)-N1-benzoyl-2-{4'-acetoxy-1'-phenyl-3'-(t-butyldiphenylsilyloxymethyl)-2',6'-dioxabicyclo[3.3.0]oct-7'-yl}-4-methyl-3-pyrazolin-5-one (1195199-14-4) + (1'S,3'R,4'R,5'R,7'R)-N2-benzoyl-1-{4'-acetoxy-1'-phenyl-3'-(t-butyldiphenylsilyloxymethyl)-2',6'-dioxabicyclo[3.3.0]oct-7'-yl}-4-methyl-3-pyrazolin-5-one (1195199-17-7) + (1'S,3'R,4'R,5'R,7'S)-N2-benzoyl-1-{4'-acetoxy-1'-phenyl-3'-(t-butyldiphenylsilyloxymethyl)-2',6'-dioxabicyclo[3.3.0]oct-7'-yl}-4-methyl-3-pyrazolin-5-one (1195199-21-3)

Guidance literature:

4-methyl-1,2-dihydro-pyrazol-3-one; benzoyl chloride; With pyridine; for 2.5h;

With N,O-Bis(trimethylsilyl)acetamide; In acetonitrile;

(1R,3R,4R,5R,7RS)-1-phenyl-3-(tert-butyldiphenylsilyloxymethyl)-4,7-diacetoxy-2,6-dioxabicylco[3.3.0]octane; With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; for 3h;

DOI:10.1016/j.bmc.2009.08.040

Reference yield: 42.0%

(1'S,3'R,4'R,5'R,7'R)-N2-benzoyl-1-{4'-acetoxy-1'-phenyl-3'-(t-butyldiphenylsilyloxymethyl)-2',6'-dioxabicyclo[3.3.0]oct-7'-yl}-4-methyl-3-pyrazolin-5-one (1195199-17-7) → WNA-1αMP (1195199-30-4)

Guidance literature:

(1'S,3'R,4'R,5'R,7'R)-N₂-benzoyl-1-{4'-acetoxy-1'-phenyl-3'-(t-butyldiphenylsilyloxymethyl)-2',6'-dioxabicyclo[3.3.0]oct-7'-yl}-4-methyl-3-pyrazolin-5-one; With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 3.5h;

With methanol; sodium hydroxide; In water; at 0 ℃; for 2.5h;

DOI:10.1016/j.bmc.2009.08.040

upstream raw materials:

4-methyl-1,2-dihydro-pyrazol-3-one

benzoyl chloride

(1R,3R,4R,5R,7RS)-1-phenyl-3-(tert-butyldiphenylsilyloxymethyl)-4,7-diacetoxy-2,6-dioxabicylco[3.3.0]octane

Downstream raw materials:

WNA-1αMP

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