7-ALLYL-7 8-DIHYDRO-8-OXOGUANOSINE 95

Base Information

• Chemical Name: 7-ALLYL-7 8-DIHYDRO-8-OXOGUANOSINE 95
• CAS No.: 121288-39-9
• Molecular Formula: C13H17N5O6
• Molecular Weight: 339.30
• Hs Code.: 29349990
• Mol file: 121288-39-9.mol

Synonyms:7-Allyl-2-amino-9-beta-D-ribofuranosylpurine-6,8(1H,9H)-dione;Loxoribinum;RWJ 21757;UNII-9CAS0V66OI;Guanosine, 7,8-dihydro-8-oxo-7-(2-propenyl)-;7-Allyl-2-amino-9b-D-ribofuranosylpurine-6,8(1H,9H)-dione;7-Allyl-8-oxoguanosine;9-[(4S,2R,3R,5R)-3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-amino-7-prop-2-enyl-1,7-dihydropurine-6,8-dione;7,8-Dihydro-8-oxo-7-(2-propenyl)guanosine;2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-enyl-3H-purine-6,8-dione;

Chemical Property of 7-ALLYL-7 8-DIHYDRO-8-OXOGUANOSINE 95

Chemical Property:

• Vapor Pressure: 1.81E-16mmHg at 25°C
• Melting Point: 227-230 °C(lit.)
• Refractive Index: 1.812
• Boiling Point: 591.8 °C at 760 mmHg
• PKA: 10.29±0.20(Predicted)
• Flash Point: 311.7 °C
• PSA: 168.62000
• Density: 1.92 g/cm³
• LogP: -2.15280
• Storage Temp.: Desiccate at +4°C
• Solubility.: Soluble in DMSO (up to 25 mg/ml).

Purity/Quality:

98%,99%, ^*data from raw suppliers

RWJ 21757 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Description: Loxoribine is a guanosine derivative and an agonist of toll-like receptor 7 (TLR7). It is selective for TLR7 over other human TLRs in a cell-based reporter assay at 1 mM.. Loxoribine induces proliferation, increases the antibody response to sheep red blood cells, and activates natural killer cell activity against Yac-1 lymphoma cells in murine splenocyte cultures (EC50s = 10-50, 3-20, and 13-22 μM, respectively). Loxoribine (250 μM) increases production of IL-12, IL-23, IL-27, and IL-10 by human monocyte-derived dendritic cells (MoDCs). Loxoribine-treated MoDCs induce higher levels of IL-17 and IFN-γ secretion by co-cultured allogeneic CD4+ T cells compared to control MoDCs. Loxoribine (120 mg/kg) reduces the number of pulmonary metastases in the B16 mouse model of melanoma, an effect enhanced by co-administration of IL-2, and exhibits adjuvant activity in mice immunized with a B16 tumor vaccine.
• Uses: 7-Allyl-7,8-dihydro-8-oxoguanosine (Loxoribine) is a small-molecule immunostimulant. Loxoribine is a toll-like receptor 7 (TLR7) agonist; induces immune cell activation and increases cytokine product ion. Loxoribine displays antitumor and antiviral activity in various animal models. Loxoribine is a selective toll-like receptor 7 (TLR7) agonist that activates immune cells and increases cytokine production. Small-molecule immunostimulants

Technology Process of 7-ALLYL-7 8-DIHYDRO-8-OXOGUANOSINE 95

There total 4 articles about 7-ALLYL-7 8-DIHYDRO-8-OXOGUANOSINE 95 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: 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: 40.0%

→ loxoribine (121288-39-9)

Guidance literature:

Reference yield:

8-bromoguanosine (4016-63-1) → loxoribine (121288-39-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / allyl alcohol / dimethylsulfoxide

2: H₂O; ethanol / Heating

With allyl alcohol; In ethanol; water; dimethyl sulfoxide;

DOI:10.1021/jm00047a014

upstream raw materials:

8-(allyloxy)-2-amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-1H-purin-6(9H)-one

1-amino-8-hydroxyguanosine

allyl bromide

8-bromoguanosine

Downstream raw materials:

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

2-amino-7-(2-propenyl)-9-<2'--3',5'-(tetraisopropyldisiloxanediyl)-β-D-ribofuranosyl>purine-6,8(1H)-dione

Refernces

• 1、 -. "IMMUNOMODULATORY CONJUGATES". Page/Page column 108. . Retrieved 2013/05/23.
• 2、 -. "Immunostimulating guanine derivatives, compositions and methods". . . Retrieved 2008/06/13.