Phosphoric acid dibenzyl ester (2R,3R,4S)-2,3,4-tris-benzyloxy-4-benzyloxycarbamoyl-butyl ester

Base Information

• Chemical Name: Phosphoric acid dibenzyl ester (2R,3R,4S)-2,3,4-tris-benzyloxy-4-benzyloxycarbamoyl-butyl ester
• CAS No.: 175844-88-9
• Molecular Formula: C₄₇H₄₈NO₉P
• Molecular Weight: 801.873

Synonyms:Phosphoric acid dibenzyl ester (2R,3R,4S)-2,3,4-tris-benzyloxy-4-benzyloxycarbamoyl-butyl ester

Chemical Property of Phosphoric acid dibenzyl ester (2R,3R,4S)-2,3,4-tris-benzyloxy-4-benzyloxycarbamoyl-butyl ester

Chemical Property:

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Technology Process of Phosphoric acid dibenzyl ester (2R,3R,4S)-2,3,4-tris-benzyloxy-4-benzyloxycarbamoyl-butyl ester

There total 5 articles about Phosphoric acid dibenzyl ester (2R,3R,4S)-2,3,4-tris-benzyloxy-4-benzyloxycarbamoyl-butyl ester 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%

O-benzylhydoxylamine hydrochloride (2687-43-6) + (2S,3R,4R)-2,3,4-Tris-benzyloxy-5-(bis-benzyloxy-phosphoryloxy)-pentanoic acid (175844-87-8) → Phosphoric acid dibenzyl ester (2R,3R,4S)-2,3,4-tris-benzyloxy-4-benzyloxycarbamoyl-butyl ester (175844-88-9)

Guidance literature:

With 1,1'-carbonyldiimidazole; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0040-4039(96)00004-4

Reference yield:

Dibenzyl N,N-diisopropylphosphoramidite (108549-23-1) → Phosphoric acid dibenzyl ester (2R,3R,4S)-2,3,4-tris-benzyloxy-4-benzyloxycarbamoyl-butyl ester (175844-88-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent

2: HgCl₂, CaCO₃ / acetonitrile; H₂O

3: PDC / dimethylformamide

4: 84 percent / carbonyldiimidazole / CH₂Cl₂; dimethylformamide

With dipyridinium dichromate; 1,1'-carbonyldiimidazole; calcium carbonate; mercury dichloride; In dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/0040-4039(96)00004-4

Reference yield:

2,3,4-tri-O-benzyl-D-arabinose diethyl dithioacetal (108713-91-3) → Phosphoric acid dibenzyl ester (2R,3R,4S)-2,3,4-tris-benzyloxy-4-benzyloxycarbamoyl-butyl ester (175844-88-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent

2: HgCl₂, CaCO₃ / acetonitrile; H₂O

3: PDC / dimethylformamide

4: 84 percent / carbonyldiimidazole / CH₂Cl₂; dimethylformamide

With dipyridinium dichromate; 1,1'-carbonyldiimidazole; calcium carbonate; mercury dichloride; In dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/0040-4039(96)00004-4

upstream raw materials:

O-benzylhydoxylamine hydrochloride

(2S,3R,4R)-2,3,4-Tris-benzyloxy-5-(bis-benzyloxy-phosphoryloxy)-pentanoic acid

Dibenzyl N,N-diisopropylphosphoramidite

2,3,4-tri-O-benzyl-D-arabinose diethyl dithioacetal

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