(S)-3-[9-(2-deoxy-β-D-erythro-pentofuranosyl)purin-6-yl]-2-[(benzyloxycarbonyl)amino]propanoic acid

Base Information

Chemical Name:(S)-3-[9-(2-deoxy-β-D-erythro-pentofuranosyl)purin-6-yl]-2-[(benzyloxycarbonyl)amino]propanoic acid
CAS No.:807626-45-5
Molecular Formula:C₂₁H₂₃N₅O₇
Molecular Weight:457.443
Hs Code.:

Synonyms:(S)-3-[9-(2-deoxy-β-D-erythro-pentofuranosyl)purin-6-yl]-2-[(benzyloxycarbonyl)amino]propanoic acid

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Chemical Property of (S)-3-[9-(2-deoxy-β-D-erythro-pentofuranosyl)purin-6-yl]-2-[(benzyloxycarbonyl)amino]propanoic acid

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Technology Process of (S)-3-[9-(2-deoxy-β-D-erythro-pentofuranosyl)purin-6-yl]-2-[(benzyloxycarbonyl)amino]propanoic acid

There total 4 articles about (S)-3-[9-(2-deoxy-β-D-erythro-pentofuranosyl)purin-6-yl]-2-[(benzyloxycarbonyl)amino]propanoic acid 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: 95.0%

: 807626-41-1
benzyl (S)-3-[9-(3,5-di-O-p-toluoyl-2-deoxy-β-D-erythro-pentofuranosyl)purin-6-yl]-2-[(benzyloxycarbonyl)amino]propanoate

: 807626-45-5
(S)-3-[9-(2-deoxy-β-D-erythro-pentofuranosyl)purin-6-yl]-2-[(benzyloxycarbonyl)amino]propanoic acid

Guidance literature:: With sodium hydroxide; In tetrahydrofuran; methanol; water; at 20 ℃; for 0.666667h;
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

: 807626-45-5
(S)-3-[9-(2-deoxy-β-D-erythro-pentofuranosyl)purin-6-yl]-2-[(benzyloxycarbonyl)amino]propanoic acid

Guidance literature:: Multi-step reaction with 3 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: 95 percent / tris(dibenzylideneacetone)dipalladium; tri(o-tolyl)phosphine / dimethylformamide / 20 °C

3.1: 95 percent / sodium hydroxide / tetrahydrofuran; methanol; H₂O / 0.67 h / 20 °C

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

Reference yield:

: 2545-26-8
6-iodopurine

: 807626-45-5
(S)-3-[9-(2-deoxy-β-D-erythro-pentofuranosyl)purin-6-yl]-2-[(benzyloxycarbonyl)amino]propanoic acid

Guidance literature:: Multi-step reaction with 3 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: 95 percent / tris(dibenzylideneacetone)dipalladium; tri(o-tolyl)phosphine / dimethylformamide / 20 °C

3.1: 95 percent / sodium hydroxide / tetrahydrofuran; methanol; H₂O / 0.67 h / 20 °C

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