8-(Allyloxy)guanosine

Base Information

• Chemical Name: 8-(Allyloxy)guanosine
• CAS No.: 126138-81-6
• Molecular Formula: C13H17N5O6
• Molecular Weight: 339.308
• Mol file: 126138-81-6.mol

Synonyms:8-(2-Propenyloxy)guanosine;

Chemical Property of 8-(Allyloxy)guanosine

Chemical Property:

• Appearance/Colour: Off-White Solid
• Refractive Index: 1.789
• PSA: 168.74000
• Density: 1.892 g/cm³
• LogP: -1.54070
• Solubility.: Dimethyl Sulfoxide, Dimethylformamide

Purity/Quality:

99% ^*data from raw suppliers

8-(Allyloxy)guanosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: A guanosine derivative as an immunostimulant.

Technology Process of 8-(Allyloxy)guanosine

There total 1 articles about 8-(Allyloxy)guanosine 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: 20.0%

8-bromoguanosine (4016-63-1) → Allyl ether (557-40-4) + 8-(allyloxy)-2-amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-1H-purin-6(9H)-one (126138-81-6)

Guidance literature:

With acetic acid; In water; dimethyl sulfoxide;

Reference yield: 100.0%

8-(allyloxy)-2-amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-1H-purin-6(9H)-one (126138-81-6) → loxoribine (121288-39-9)

Guidance literature:

With methanol; In water; for 20h; Time; Reflux;

Reference yield:

8-(allyloxy)-2-amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-1H-purin-6(9H)-one (126138-81-6) → 2-amino-7-(2-propenyl)-9-<2(R)-<4-(diphenylmethyl)-6(S)-(hydroxymethyl)morpholino>>purine-6,8(1H)-dione

Guidance literature:

Multi-step reaction with 3 steps

1: H₂O; ethanol / Heating

2: NaIO₄ / H₂O / 6 h / Ambient temperature

3: NaCNBH₃ / acetic acid

With sodium periodate; sodium cyanoborohydride; In ethanol; water; acetic acid;

DOI:10.1021/jm00047a014

upstream raw materials:

8-bromoguanosine

Downstream raw materials:

loxoribine

2-amino-7-(2-propenyl)-9-<5'-(tert-butyldiphenylsilyl)-β-D-ribofuranosyl>purine-6,8(1H)-dione

Phosphoric acid (2R,3S,4R,5R)-5-(7-allyl-2-amino-6,8-dioxo-1,6,7,8-tetrahydro-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester diphenyl ester

7-Allyl-2-amino-9-[(3aR,4R,6R,6aR)-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-7,9-dihydro-1H-purine-6,8-dione

Refernces