benzyl 3-[9-(3,5-di-O-p-toluoyl-2-deoxy-β-D-erythro-pentofuranosyl)purin-6-yl]-2-[(benzyloxycarbonyl)amino]propanoate

Base Information

Chemical Name:benzyl 3-[9-(3,5-di-O-p-toluoyl-2-deoxy-β-D-erythro-pentofuranosyl)purin-6-yl]-2-[(benzyloxycarbonyl)amino]propanoate
CAS No.:787550-85-0
Molecular Formula:C₄₄H₄₁N₅O₉
Molecular Weight:783.838
Hs Code.:

Synonyms:benzyl 3-[9-(3,5-di-O-p-toluoyl-2-deoxy-β-D-erythro-pentofuranosyl)purin-6-yl]-2-[(benzyloxycarbonyl)amino]propanoate

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Chemical Property of benzyl 3-[9-(3,5-di-O-p-toluoyl-2-deoxy-β-D-erythro-pentofuranosyl)purin-6-yl]-2-[(benzyloxycarbonyl)amino]propanoate

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Technology Process of benzyl 3-[9-(3,5-di-O-p-toluoyl-2-deoxy-β-D-erythro-pentofuranosyl)purin-6-yl]-2-[(benzyloxycarbonyl)amino]propanoate

There total 4 articles about benzyl 3-[9-(3,5-di-O-p-toluoyl-2-deoxy-β-D-erythro-pentofuranosyl)purin-6-yl]-2-[(benzyloxycarbonyl)amino]propanoate 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: 96.0%

: 65926-39-8
2-Benzyloxycarbonylamino-3-iodo-propionic acid benzyl ester

: 756494-16-3
9-[2-deoxy-3,5-di-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl]-6-iodopurine

: 787550-85-0
benzyl 3-[9-(3,5-di-O-p-toluoyl-2-deoxy-β-D-erythro-pentofuranosyl)purin-6-yl]-2-[(benzyloxycarbonyl)amino]propanoate

Guidance literature:: 2-Benzyloxycarbonylamino-3-iodo-propionic acid benzyl ester; With chloro-trimethyl-silane; zinc; In N,N-dimethyl-formamide; at 20 ℃; for 0.666667h; sonication;

9-[2-deoxy-3,5-di-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl]-6-iodopurine; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tris-(o-tolyl)phosphine; In N,N-dimethyl-formamide; at 20 ℃;
DOI:10.1021/jo048812r

Reference yield:

: 3056-12-0,3601-89-6,4330-21-6,52304-86-6,141846-57-3
2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythropentofuranosyl chloride

: 787550-85-0
benzyl 3-[9-(3,5-di-O-p-toluoyl-2-deoxy-β-D-erythro-pentofuranosyl)purin-6-yl]-2-[(benzyloxycarbonyl)amino]propanoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 61 percent / NaH / acetonitrile / 18 h / 20 °C

2.1: zinc; trimethylsilyl chloride / dimethylformamide / 0.67 h / 20 °C / sonication

2.2: 96 percent / tris(dibenzylideneacetone)dipalladium; tri(o-tolyl)phosphine / dimethylformamide / 20 °C

With chloro-trimethyl-silane; sodium hydride; zinc; In N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo048812r

Reference yield:

: 2545-26-8
6-iodopurine

: 787550-85-0
benzyl 3-[9-(3,5-di-O-p-toluoyl-2-deoxy-β-D-erythro-pentofuranosyl)purin-6-yl]-2-[(benzyloxycarbonyl)amino]propanoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 61 percent / NaH / acetonitrile / 18 h / 20 °C

2.1: zinc; trimethylsilyl chloride / dimethylformamide / 0.67 h / 20 °C / sonication

2.2: 96 percent / tris(dibenzylideneacetone)dipalladium; tri(o-tolyl)phosphine / dimethylformamide / 20 °C

With chloro-trimethyl-silane; sodium hydride; zinc; In N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo048812r