(2R)-N-(2',3',4'-tri-O-pivaloyl-α-D-arabinopyranosyl)-2-(p-chlorophenyl)-5-iodo-5,6-dehydropiperidin-4-one

Base Information

• Chemical Name: (2R)-N-(2',3',4'-tri-O-pivaloyl-α-D-arabinopyranosyl)-2-(p-chlorophenyl)-5-iodo-5,6-dehydropiperidin-4-one
• CAS No.: 901759-87-3
• Molecular Formula: C₃₁H₄₁ClINO₈
• Molecular Weight: 718.026
• Mol file: 901759-87-3.mol

Synonyms:(2R)-N-(2',3',4'-tri-O-pivaloyl-α-D-arabinopyranosyl)-2-(p-chlorophenyl)-5-iodo-5,6-dehydropiperidin-4-one

Chemical Property of (2R)-N-(2',3',4'-tri-O-pivaloyl-α-D-arabinopyranosyl)-2-(p-chlorophenyl)-5-iodo-5,6-dehydropiperidin-4-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R)-N-(2',3',4'-tri-O-pivaloyl-α-D-arabinopyranosyl)-2-(p-chlorophenyl)-5-iodo-5,6-dehydropiperidin-4-one

There total 1 articles about (2R)-N-(2',3',4'-tri-O-pivaloyl-α-D-arabinopyranosyl)-2-(p-chlorophenyl)-5-iodo-5,6-dehydropiperidin-4-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: 93.0%

2,2-Dimethyl-propionic acid (2S,3S,4R,5R)-2-[(R)-2-(4-chloro-phenyl)-4-oxo-3,4-dihydro-2H-pyridin-1-yl]-4,5-bis-(2,2-dimethyl-propionyloxy)-tetrahydro-pyran-3-yl ester (686341-86-6) → (2R)-N-(2',3',4'-tri-O-pivaloyl-α-D-arabinopyranosyl)-2-(p-chlorophenyl)-5-iodo-5,6-dehydropiperidin-4-one (901759-87-3)

Guidance literature:

With N-iodo-succinimide; In tetrahydrofuran; at -78 ℃;

DOI:10.1039/b615113b

Reference yield: 71.0%

(2R)-N-(2',3',4'-tri-O-pivaloyl-α-D-arabinopyranosyl)-2-(p-chlorophenyl)-5-iodo-5,6-dehydropiperidin-4-one (901759-87-3) + allyl bromide (106-95-6) → (2R)-N-(2',3',4'-tri-O-pivaloyl-α-D-arabinopyranosyl)-5-allyl-2-(p-chlorophenyl)-5,6-dehydropiperidin-4-one

Guidance literature:

(2R)-N-(2',3',4'-tri-O-pivaloyl-α-D-arabinopyranosyl)-2-(p-chlorophenyl)-5-iodo-5,6-dehydropiperidin-4-one; With isopropylmagnesium bromide; In tetrahydrofuran; at -30 ℃; for 1h;

In tetrahydrofuran; at -30 ℃; for 0.5h;

allyl bromide; In tetrahydrofuran; at 20 ℃; for 5h; Further stages.;

DOI:10.1039/b615113b

Reference yield: 51.0%

(2R)-N-(2',3',4'-tri-O-pivaloyl-α-D-arabinopyranosyl)-2-(p-chlorophenyl)-5-iodo-5,6-dehydropiperidin-4-one (901759-87-3) + methyl 4-iodobenzoate (619-44-3) → (2R)-N-(2',3',4'-tri-O-pivaloyl-α-D-arabinopyranosyl)-2-(p-chlorophenyl)-5-p-(methoxycarbonyl)phenyl-5,6-dehydropiperidin-4-one

Guidance literature:

(2R)-N-(2',3',4'-tri-O-pivaloyl-α-D-arabinopyranosyl)-2-(p-chlorophenyl)-5-iodo-5,6-dehydropiperidin-4-one; With isopropylmagnesium bromide; In tetrahydrofuran; at -30 ℃; for 2h;

With zinc dibromide; In tetrahydrofuran; at -30 - 20 ℃;

methyl 4-iodobenzoate; With triphenyl-arsane; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; at 40 ℃; Further stages.;

DOI:10.1039/b615113b

upstream raw materials:

2,2-Dimethyl-propionic acid (2S,3S,4R,5R)-2-[(R)-2-(4-chloro-phenyl)-4-oxo-3,4-dihydro-2H-pyridin-1-yl]-4,5-bis-(2,2-dimethyl-propionyloxy)-tetrahydro-pyran-3-yl ester