9-(2-O-acetyl-3-O-benzyl-4C-methanesulfonyloxymethyl-5-O-methanesulfonyl-β-D-erythro-pentofuranosyl)-2-amino-6-chloropurine

Base Information

Chemical Name:9-(2-O-acetyl-3-O-benzyl-4C-methanesulfonyloxymethyl-5-O-methanesulfonyl-β-D-erythro-pentofuranosyl)-2-amino-6-chloropurine
CAS No.:405290-35-9
Molecular Formula:C₂₂H₂₆ClN₅O₁₀S₂
Molecular Weight:620.061
Hs Code.:

Synonyms:9-(2-O-acetyl-3-O-benzyl-4C-methanesulfonyloxymethyl-5-O-methanesulfonyl-β-D-erythro-pentofuranosyl)-2-amino-6-chloropurine

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Chemical Property of 9-(2-O-acetyl-3-O-benzyl-4C-methanesulfonyloxymethyl-5-O-methanesulfonyl-β-D-erythro-pentofuranosyl)-2-amino-6-chloropurine

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Technology Process of 9-(2-O-acetyl-3-O-benzyl-4C-methanesulfonyloxymethyl-5-O-methanesulfonyl-β-D-erythro-pentofuranosyl)-2-amino-6-chloropurine

There total 8 articles about 9-(2-O-acetyl-3-O-benzyl-4C-methanesulfonyloxymethyl-5-O-methanesulfonyl-β-D-erythro-pentofuranosyl)-2-amino-6-chloropurine 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: 98.0%

: 10310-21-1
2-Amino-6-chloropurin

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

: 405290-35-9
9-(2-O-acetyl-3-O-benzyl-4C-methanesulfonyloxymethyl-5-O-methanesulfonyl-β-D-erythro-pentofuranosyl)-2-amino-6-chloropurine

Guidance literature:: 2-Amino-6-chloropurin; 1,2-di-O-acetyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-3-O-benzyl-D-erythro-pentofuranose; With N,O-bis-(trimethylsilyl)-acetamide; In acetonitrile; at 25 - 90 ℃; for 2.25h; Large scale;

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 85 - 90 ℃; for 1.25h; Large scale;

Reference yield:

: 63593-03-3
1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

: 405290-35-9
9-(2-O-acetyl-3-O-benzyl-4C-methanesulfonyloxymethyl-5-O-methanesulfonyl-β-D-erythro-pentofuranosyl)-2-amino-6-chloropurine

Guidance literature:: Multi-step reaction with 3 steps

1.1: pyridine / 1 h / 20 °C

2.1: sulfuric acid / acetic acid / 20 °C

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

3.2: 3 h / Reflux; Inert atmosphere

With pyridine; N,O-bis-(trimethylsilyl)-acetamide; sulfuric acid; In acetic acid; 1,2-dichloro-ethane;
DOI:10.1016/j.bmcl.2014.04.050

Reference yield:

: 22331-21-1
1,2:5,6-di-O-isopropylidene-3-O-benzyl-α-D-allofuranose

: 405290-35-9
9-(2-O-acetyl-3-O-benzyl-4C-methanesulfonyloxymethyl-5-O-methanesulfonyl-β-D-erythro-pentofuranosyl)-2-amino-6-chloropurine

Guidance literature:: Multi-step reaction with 6 steps

1.1: acetic acid / water / 72 h / 20 °C

2.1: sodium periodate / water / 1 h / 0 °C

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

4.1: pyridine / 1 h / 20 °C

5.1: sulfuric acid / acetic acid / 20 °C

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

6.2: 3 h / Reflux; Inert atmosphere

With pyridine; sodium periodate; N,O-bis-(trimethylsilyl)-acetamide; sulfuric acid; acetic acid; sodium hydroxide; In 1,4-dioxane; water; acetic acid; 1,2-dichloro-ethane;
DOI:10.1016/j.bmcl.2014.04.050