2-amino-9-((1R,3R,4R,7S)-7-(benzyloxy)-1-(((tert-butyldimethylsilyl)oxy)methyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-1H-purin-6(9H)-one

Base Information

Chemical Name:2-amino-9-((1R,3R,4R,7S)-7-(benzyloxy)-1-(((tert-butyldimethylsilyl)oxy)methyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-1H-purin-6(9H)-one
CAS No.:1610605-77-0
Molecular Formula:C₂₄H₃₃N₅O₅Si
Molecular Weight:499.642
Hs Code.:

Synonyms:2-amino-9-((1R,3R,4R,7S)-7-(benzyloxy)-1-(((tert-butyldimethylsilyl)oxy)methyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-1H-purin-6(9H)-one

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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 2-amino-9-((1R,3R,4R,7S)-7-(benzyloxy)-1-(((tert-butyldimethylsilyl)oxy)methyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-1H-purin-6(9H)-one

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of 2-amino-9-((1R,3R,4R,7S)-7-(benzyloxy)-1-(((tert-butyldimethylsilyl)oxy)methyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-1H-purin-6(9H)-one

There total 11 articles about 2-amino-9-((1R,3R,4R,7S)-7-(benzyloxy)-1-(((tert-butyldimethylsilyl)oxy)methyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-1H-purin-6(9H)-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: 70.0%

: 293751-16-3
(1S,3R,4R,7S)-7-benzyloxy-1-hydroxymethyl-3-(guanin-9-yl)-2,5-dioxabicyclo[2.2.1]heptane

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1610605-77-0
2-amino-9-((1R,3R,4R,7S)-7-(benzyloxy)-1-(((tert-butyldimethylsilyl)oxy)methyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-1H-purin-6(9H)-one

Guidance literature:: With dmap; In pyridine; dichloromethane; at 20 ℃; for 72h;
DOI:10.1016/j.bmcl.2014.04.050

Reference yield:

: 3-O-benzyl-1,2-O-isopropylidene-α-D-ribo-pentodialdofuranose

: 1610605-77-0
2-amino-9-((1R,3R,4R,7S)-7-(benzyloxy)-1-(((tert-butyldimethylsilyl)oxy)methyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-1H-purin-6(9H)-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: sodium hydroxide / water; 1,4-dioxane / 144 h / 0 - 20 °C

2.1: pyridine / 1 h / 20 °C

3.1: sulfuric acid / acetic acid / 20 °C

4.1: N,O-bis-(trimethylsilyl)-acetamide / 1,2-dichloro-ethane / 1 h / Reflux

4.2: 3 h / Reflux; Inert atmosphere

5.1: 3-Hydroxypropionitrile; sodium hydride / mineral oil; tetrahydrofuran / 18 h / 0 - 20 °C

6.1: dimethyl sulfoxide / 5 h / 100 °C

7.1: ammonia / methanol / 18 h / 20 °C / Sealed tube

8.1: dmap / dichloromethane; pyridine / 72 h / 20 °C

With pyridine; dmap; N,O-bis-(trimethylsilyl)-acetamide; sulfuric acid; ammonia; sodium hydride; 3-Hydroxypropionitrile; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; dichloromethane; water; acetic acid; dimethyl sulfoxide; 1,2-dichloro-ethane; mineral oil;
DOI:10.1016/j.bmcl.2014.04.050

Reference yield:

: 293751-03-8
1,2-di-O-acetyl-3-O-benzyl-4-C-methanesulfonyloxymethyl-5-O-methanesulfonyl-D-erythro-pentofuranose

: 1610605-77-0
2-amino-9-((1R,3R,4R,7S)-7-(benzyloxy)-1-(((tert-butyldimethylsilyl)oxy)methyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-1H-purin-6(9H)-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: N,O-bis-(trimethylsilyl)-acetamide / 1,2-dichloro-ethane / 1 h / Reflux

1.2: 3 h / Reflux; Inert atmosphere

2.1: 3-Hydroxypropionitrile; sodium hydride / mineral oil; tetrahydrofuran / 18 h / 0 - 20 °C

3.1: dimethyl sulfoxide / 5 h / 100 °C

4.1: ammonia / methanol / 18 h / 20 °C / Sealed tube

5.1: dmap / dichloromethane; pyridine / 72 h / 20 °C

With dmap; N,O-bis-(trimethylsilyl)-acetamide; ammonia; sodium hydride; 3-Hydroxypropionitrile; In tetrahydrofuran; pyridine; methanol; dichloromethane; dimethyl sulfoxide; 1,2-dichloro-ethane; mineral oil;
DOI:10.1016/j.bmcl.2014.04.050