(1S,3R,4R,7S)-3-(2-amino-6-chloropurin-9-yl)-7-benzyloxy-1-methanesulfonyloxymethyl-2,5-dioxabicyclo[2.2.1]heptane

Base Information

• Chemical Name: (1S,3R,4R,7S)-3-(2-amino-6-chloropurin-9-yl)-7-benzyloxy-1-methanesulfonyloxymethyl-2,5-dioxabicyclo[2.2.1]heptane
• CAS No.: 675848-74-5
• Molecular Formula: C₁₉H₂₀ClN₅O₆S
• Molecular Weight: 481.917
• Mol file: 675848-74-5.mol

Synonyms:(1S,3R,4R,7S)-3-(2-amino-6-chloropurin-9-yl)-7-benzyloxy-1-methanesulfonyloxymethyl-2,5-dioxabicyclo[2.2.1]heptane

Chemical Property of (1S,3R,4R,7S)-3-(2-amino-6-chloropurin-9-yl)-7-benzyloxy-1-methanesulfonyloxymethyl-2,5-dioxabicyclo[2.2.1]heptane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3R,4R,7S)-3-(2-amino-6-chloropurin-9-yl)-7-benzyloxy-1-methanesulfonyloxymethyl-2,5-dioxabicyclo[2.2.1]heptane

There total 8 articles about (1S,3R,4R,7S)-3-(2-amino-6-chloropurin-9-yl)-7-benzyloxy-1-methanesulfonyloxymethyl-2,5-dioxabicyclo[2.2.1]heptane 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: 90.0%

9-(2-O-acetyl-3-O-benzyl-4C-methanesulfonyloxymethyl-5-O-methanesulfonyl-β-D-erythro-pentofuranosyl)-2-amino-6-chloropurine (405290-35-9) → (1S,3R,4R,7S)-3-(2-amino-6-chloropurin-9-yl)-7-benzyloxy-1-methanesulfonyloxymethyl-2,5-dioxabicyclo[2.2.1]heptane (675848-74-5)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 0.75h;

DOI:10.1016/j.bmc.2004.02.008

Reference yield:

1,2-di-O-acetyl-3-O-benzyl-4-C-methanesulfonyloxymethyl-5-O-methanesulfonyl-D-erythro-pentofuranose (293751-03-8) → (1S,3R,4R,7S)-3-(2-amino-6-chloropurin-9-yl)-7-benzyloxy-1-methanesulfonyloxymethyl-2,5-dioxabicyclo[2.2.1]heptane (675848-74-5)

Guidance literature:

Multi-step reaction with 2 steps

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

1.2: 90 percent / trimethylsilyl triflate / 1,2-dichloro-ethane / 3 h / Heating

2.1: 90 percent / LiOH / tetrahydrofuran; H₂O / 0.75 h / 20 °C

With lithium hydroxide; N,O-bis-(trimethylsilyl)-acetamide; In tetrahydrofuran; water; 1,2-dichloro-ethane; 1.1: Vorbrueggen coupling;

DOI:10.1016/j.bmc.2004.02.008

Reference yield:

2-Amino-6-chloropurin (10310-21-1) → (1S,3R,4R,7S)-3-(2-amino-6-chloropurin-9-yl)-7-benzyloxy-1-methanesulfonyloxymethyl-2,5-dioxabicyclo[2.2.1]heptane (675848-74-5)

Guidance literature:

Multi-step reaction with 2 steps

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

1.2: 90 percent / trimethylsilyl triflate / 1,2-dichloro-ethane / 3 h / Heating

2.1: 90 percent / LiOH / tetrahydrofuran; H₂O / 0.75 h / 20 °C

With lithium hydroxide; N,O-bis-(trimethylsilyl)-acetamide; In tetrahydrofuran; water; 1,2-dichloro-ethane; 1.1: Vorbrueggen coupling;

DOI:10.1016/j.bmc.2004.02.008

upstream raw materials:

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

2-Amino-6-chloropurin

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

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

Downstream raw materials:

Benzoic acid (1R,3R,4R,7S)-3-(2-amino-6-azido-purin-9-yl)-7-benzyloxy-2,5-dioxa-bicyclo[2.2.1]hept-1-ylmethyl ester

(1S,3R,4R,7S)-3-(2-amino-6-azidopurin-9-yl)-7-benzyloxy-1-hydroxymethyl-2,5-dioxabicyclo[2.2.1]heptane

(1S,3R,4R,7S)-3-(2-amino-6-chloropurin-9-yl)-7-benzyloxy-1-hydroxymethyl-2,5-dioxabicyclo[2.2.1]heptane

(1R,3R,4R,7S)-3-(2,6-di(N-benzoylamino)purin-9-yl)-1-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptane