(2R,3R,4R,5R)-2-(4-amino-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(benzoyloxymethyl)-3-methyltetrahydrofuran-3,4-diyl dibenzoate

Base Information

Chemical Name:(2R,3R,4R,5R)-2-(4-amino-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(benzoyloxymethyl)-3-methyltetrahydrofuran-3,4-diyl dibenzoate
CAS No.:729595-78-2
Molecular Formula:C₃₄H₂₇N₅O₇
Molecular Weight:617.618
Hs Code.:

Synonyms:(2R,3R,4R,5R)-2-(4-amino-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(benzoyloxymethyl)-3-methyltetrahydrofuran-3,4-diyl dibenzoate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2R,3R,4R,5R)-2-(4-amino-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(benzoyloxymethyl)-3-methyltetrahydrofuran-3,4-diyl dibenzoate

Chemical Property:

Purity/Quality:: 97% ^*data from raw suppliers

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Technology Process of (2R,3R,4R,5R)-2-(4-amino-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(benzoyloxymethyl)-3-methyltetrahydrofuran-3,4-diyl dibenzoate

There total 4 articles about (2R,3R,4R,5R)-2-(4-amino-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(benzoyloxymethyl)-3-methyltetrahydrofuran-3,4-diyl dibenzoate 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: 97.0%

: 729595-79-3
(2R,3R,4R,5R)-2-(4-amino-6-bromo-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(benzoyloxymethyl)-3-methyltetrahydrofuran-3,4-diyl dibenzoate

: 729595-78-2
(2R,3R,4R,5R)-2-(4-amino-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(benzoyloxymethyl)-3-methyltetrahydrofuran-3,4-diyl dibenzoate

Guidance literature:: With hydrogen; triethylamine; palladium on activated charcoal; In 1,4-dioxane; under 1551.44 Torr;
DOI:10.1016/j.bmcl.2004.04.067

Reference yield: 34.0%

: (3R,4R,5R)-2-(4-amino-6-bromo-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(benzoyloxymethyl)-3-methyltetrahydrofuran-3,4-diyl dibenzoate

: 729595-78-2
(2R,3R,4R,5R)-2-(4-amino-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(benzoyloxymethyl)-3-methyltetrahydrofuran-3,4-diyl dibenzoate

Guidance literature:: With ammonium formate; 5% Pd(II)/C(eggshell); In methanol; ethyl acetate; at 20 ℃; for 23.5h; Reflux;

Reference yield:

: 19393-83-0
4-amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidine

: 729595-78-2
(2R,3R,4R,5R)-2-(4-amino-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(benzoyloxymethyl)-3-methyltetrahydrofuran-3,4-diyl dibenzoate

Guidance literature:: Multi-step reaction with 2 steps

1: 70 percent / N,O-bis(trimethylsilyl)acetamide; TMSOTf / 1,2-dichloro-ethane / 18 h / 65 °C

2: 97 percent / H₂; Et₃N / Pd/C / dioxane / 1551.44 Torr

With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; hydrogen; triethylamine; palladium on activated charcoal; In 1,4-dioxane; 1,2-dichloro-ethane;
DOI:10.1016/j.bmcl.2004.04.067