Pent-2-enofuranoside, adenine-9 2,3-dideoxy-

Base Information

• Chemical Name: Pent-2-enofuranoside, adenine-9 2,3-dideoxy-
• CAS No.: 7057-48-9
• Molecular Formula: C10H11N5O2
• Molecular Weight: 233.23
• NSC Number: 108602
• Mol file: 7057-48-9.mol

Synonyms:NSC108602;NSC-108602;Pent-2-enofuranoside, adenine-9 2,3-dideoxy-;TimTec1_003698;Oprea1_278264;Adenine, 9-(2,3-dideoxy-.beta.-D-glycero-pent-2-enofuranosyl)-;Pent-2-enofuranoside,3-dideoxy-;JFUOUIPRAAGUGF-UHFFFAOYSA-N;HMS1544I02;MFCD00040965;PB17076;Adenosine,3'-didehydro-2',3'-dideoxy-;FT-0609590;Adenine,3-dideoxy-.beta.-D-glycero-pent-2-enofuranosyl)-;[5-(6-Amino-9H-purin-9-yl)-2,5-dihydro-2-furanyl]methanol #

Chemical Property of Pent-2-enofuranoside, adenine-9 2,3-dideoxy-

Chemical Property:

• Melting Point: 187-189oC
• Boiling Point: 553.9°Cat760mmHg
• PKA: 14.28±0.10(Predicted)
• Flash Point: 288.8°C
• PSA: 99.08000
• Density: 1.74g/cm³
• LogP: 0.43560
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 233.09127461
• Heavy Atom Count: 17
• Complexity: 313

Purity/Quality:

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

2’,3’-Dideoxy-2,3-didehydroadenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(OC1CO)N2C=NC3=C(N=CN=C32)N
• Uses: 2’,3’-Dideoxy-2,3-didehydroadenosine (Didanosine EP Impurity I) is an impurity of Didanosine (D440950), which is a purine analog (1) which used as an antiviral agent. Classed as an anti-retroviral drug used in the treatment of HIV in ART therapy, it also may increase acetaminophen related hepatotoxicity by enhancing mitochrondrial dysfunction (2).

Technology Process of Pent-2-enofuranoside, adenine-9 2,3-dideoxy-

There total 1 articles about Pent-2-enofuranoside, adenine-9 2,3-dideoxy- 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:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6) → 2',3'-didehydro-2',3'-dideoxyadenosine (7057-48-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 98 percent / imidazole / dimethylformamide / 1 h / Ambient temperature

2: 1) lithium hexamethyldisilazide / 1) THF, -78 deg C, 1h, 2) room temperature, 30 min

3: tetrahydrofuran / -78 °C

4: DIBAL-H / toluene / 2 h / -78 °C

5: 96 percent / pyridine, DMAP / CH₂Cl₂ / 2 h / 0 °C

6: 1) hexamethyldisilazane (HMDS), ammonium sulfate, 2) trimethylsilyl triflate (TMSOTf) / 1) reflux, 1 h, 2) 1,2-dichloroethane, a) -22 deg C, 15 min, b) room temperature, 0.5 h

7: 59 percent / ammonia / methanol / 16 h / 80 °C

8: 66.8 percent / 30percent aq. H₂O₂, pyridine / CH₂Cl₂ / Ambient temperature

9: 97.8 percent / TBAF / tetrahydrofuran / Ambient temperature

With pyridine; 1H-imidazole; dmap; ammonium sulfate; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; ammonia; dihydrogen peroxide; diisobutylaluminium hydride; 1,1,1,3,3,3-hexamethyl-disilazane; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo00040a031

Reference yield: 89.0%

2',3'-didehydro-2',3'-dideoxyadenosine (7057-48-9) → 2',3'-Dideoxyadenosine (4097-22-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol;

DOI:10.1016/S0040-4039(00)99885-X

Reference yield: 63.0%

2',3'-didehydro-2',3'-dideoxyadenosine (7057-48-9) + (phenylmethoxy)alaninyl phosphorochloridate → 2-{[(2S,5R)-5-(6-Amino-purin-9-yl)-2,5-dihydro-furan-2-ylmethoxy]-phenoxy-phosphorylamino}-propionic acid methyl ester

Guidance literature:

With tert-butylmagnesium chloride; In tetrahydrofuran; at 20 ℃; for 5h;

DOI:10.1016/0960-894X(96)00433-7

upstream raw materials:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

Downstream raw materials:

2',3'-Dideoxyadenosine

Refernces