(3aR,4S,6aS)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methylamide

Base Information

• Chemical Name: (3aR,4S,6aS)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methylamide
• CAS No.: 39491-51-5
• Molecular Formula: C14H18N6O4
• Molecular Weight: 334.3305
• Mol file: 39491-51-5.mol

Synonyms:5'-N-methyl-2',3'-O-isopropylidenecarboxamidoadenosine;

Chemical Property of (3aR,4S,6aS)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methylamide

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 126.41000
• Density: 1.76g/cm³
• LogP: 0.54410

Purity/Quality:

97% ^*data from raw suppliers

2',3'-O-Isopropylidene-adenosine-5-N-methylcarbamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (3aR,4S,6aS)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methylamide

There total 7 articles about (3aR,4S,6aS)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methylamide 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: 84.0%

2',3'-isopropylideneadenosine-5'-carboxylic acid (19234-66-3) + methylamine (74-89-5) → 5'-N-methyl-2',3'-O-isopropylidenecarboxamidoadenosine (39491-51-5)

Guidance literature:

With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; 1-hydroxybenzotriazol-hydrate; In N,N-dimethyl-formamide; at 20 ℃; for 4h;

DOI:10.1021/ol015995k

Reference yield:

2',3'-isopropylideneadenosine-5'-carboxylic acid (19234-66-3) → 5'-N-methyl-2',3'-O-isopropylidenecarboxamidoadenosine (39491-51-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide*HCl / dimethylformamide / 3 h / 20 °C

2: dimethylformamide / 1 h / 20 °C

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide;

DOI:10.1021/jm000150k

Reference yield:

(3aS,4S,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid 4-nitro-phenyl ester (159647-45-7) + methylamine (74-89-5) → 5'-N-methyl-2',3'-O-isopropylidenecarboxamidoadenosine (39491-51-5)

Guidance literature:

In N,N-dimethyl-formamide; at 20 ℃; for 1h;

DOI:10.1021/jm000150k

upstream raw materials:

2',3'-O-isopropylideneadenosine-5'-carbonyl chloride

methylamine

2',3'-O-isopropylideneadenosine-5'-carboxylic acid methyl ester

2',3'-isopropylideneadenosine-5'-carboxylic acid

Downstream raw materials:

3-{[(3aS,4S,6R,6aR)-6-(6-Benzyloxycarbonylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbonyl]-methyl-amino}-2-diazo-3-oxo-propionic acid methyl ester

3-{[(3aS,4S,6R,6aR)-6-(6-Benzyloxycarbonylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbonyl]-methyl-amino}-3-oxo-propionic acid methyl ester

[9-((3aR,4R,6S,6aS)-2,2-Dimethyl-6-methylcarbamoyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl]-carbamic acid benzyl ester

5'-N-methylcarboxamidoadenosine