((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl sulfamate

Base Information

• Chemical Name: ((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl sulfamate
• CAS No.: 112921-00-3
• Molecular Formula: C₁₃H₁₈N₆O₆S
• Molecular Weight: 386.389
• Mol file: 112921-00-3.mol

Synonyms:((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl sulfamate

Chemical Property of ((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl sulfamate

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of ((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl sulfamate

There total 5 articles about ((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl sulfamate 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: 86.0%

2',3'-isopropylidene adenosine (362-75-4) → ((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl sulfamate (112921-00-3)

Guidance literature:

2',3'-isopropylidene adenosine; With sodium hydride; In 1,4-dioxane; at 0 ℃; for 0.5h; Inert atmosphere;

With sulphamoyl chloride; In 1,4-dioxane; at 0 - 20 ℃; for 24.5h; Inert atmosphere;

DOI:10.1016/j.molcatb.2011.01.008

Reference yield:

((3aR,4R,6R,6aR)-6-(6-amino-2-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol (24639-06-3) → ((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl sulfamate (112921-00-3)

Guidance literature:

With sulphamoyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 15h; Inert atmosphere;

DOI:10.1016/j.bmcl.2018.04.038

Reference yield:

adenosine (58-61-7) → ((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl sulfamate (112921-00-3)

Guidance literature:

Multi-step reaction with 2 steps

1: camphorsulfonic acid

2: NH₂SO₂Cl; NaH / 1,2-dimethoxy-ethane

With camphor-10-sulfonic acid; sulphamoyl chloride; sodium hydride; In 1,2-dimethoxyethane;

DOI:10.1016/S0960-894X(03)00020-9

upstream raw materials:

2',3'-isopropylidene adenosine

adenosine

2-Chloroadenosine

((3aR,4R,6R,6aR)-6-(6-amino-2-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol

Downstream raw materials:

benzyl 4-oxo-4-[5'-aminosulfamoyl-5'-deoxy-2',3'-O-isopropylidene-adenosine]-butyrate

5'-O-(N-(2-benzyloxybenzyl)sulfamoyl)-2',3'-O-isopropylideneadenosine