N6-Benzyl-2’,3’-isopropylideneadenosine

Base Information

• Chemical Name: N6-Benzyl-2’,3’-isopropylideneadenosine
• CAS No.: 78188-38-2
• Molecular Formula: C20H23 N5 O4
• Molecular Weight: 397.434
• Mol file: 78188-38-2.mol

Synonyms:Furo[3,4-d]-1,3-dioxole,adenosine deriv.

Chemical Property of N6-Benzyl-2’,3’-isopropylideneadenosine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.719
• Boiling Point: 627.035°C at 760 mmHg
• Flash Point: 333.019°C
• PSA: 103.55000
• Density: 1.518g/cm³
• LogP: 1.92120
• Storage Temp.: Refrigerator
• Solubility.: Acetone (Slightly), Chloroform (Slightly), Dichloromethane (Slightly), DMSO (Sli

Purity/Quality:

98%Min ^*data from raw suppliers

2'',3''-O-(1-Methylethylidene)-N-(phenylmethyl)adenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2'',3''-O-(1-Methylethylidene)-N-(phenylmethyl)adenosine (cas# 78188-38-2) is a compound useful in organic synthesis.

Technology Process of N6-Benzyl-2’,3’-isopropylideneadenosine

There total 6 articles about N6-Benzyl-2’,3’-isopropylideneadenosine 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: 75.0%

N6-Benzyladenosine (4294-16-0) + 2,2-dimethoxy-propane (77-76-9) → {(1R,2R,4R,5R)-4-[6-(benzylamino)purin-9-yl]-7,7-dimethyl-3,6,8-trioxabicyclo[3.3.0]oct-2-yl}methan-1-ol (78188-38-2)

Guidance literature:

With toluene-4-sulfonic acid; In acetone; at 25 ℃; for 24h;

Reference yield: 13.5%

N6,N6-dibenzyl-2',3'-O-isopropylideneadenosine (109680-72-0) → 2',3'-isopropylidene adenosine (362-75-4) + {(1R,2R,4R,5R)-4-[6-(benzylamino)purin-9-yl]-7,7-dimethyl-3,6,8-trioxabicyclo[3.3.0]oct-2-yl}methan-1-ol (78188-38-2)

Guidance literature:

With potassium permanganate; In water; acetic acid; for 0.67h; Yields of byproduct given; Ambient temperature;

DOI:10.1248/cpb.34.3635

Reference yield:

6-chloro-9-(2,3-O-isopropylidene-β-D-ribofuranosyl)-9H-purine (39824-26-5) + benzylamine (100-46-9) → {(1R,2R,4R,5R)-4-[6-(benzylamino)purin-9-yl]-7,7-dimethyl-3,6,8-trioxabicyclo[3.3.0]oct-2-yl}methan-1-ol (78188-38-2)

Guidance literature:

In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1016/j.bmcl.2015.02.017

upstream raw materials:

N⁶,N⁶-dibenzyl-2',3'-O-isopropylideneadenosine

N₆-Benzyladenosine

2,2-dimethoxy-propane

6-chloro-9-(2,3-O-isopropylidene-β-D-ribofuranosyl)-9H-purine

Downstream raw materials:

N₆-benzyl-2',3'-O-isopropylidene-5'-O-(sulfamoyl)adenosine

(S)-2-amino-4-((((2S,3S,4R,5S)-5-(6-(benzylamino)-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)thio)butanoic acid

N^δ-[5'-(N⁶-benzyladenosyl)]-N^δ-(2-iodoethyl)-(S)-2,5-diaminopentanoic acid hydrochloride

C₄₁H₆₁N₇O₁₀

Refernces

• 1、 -. "NUCLEOSIDE AND NUCLEOTIDE ANALOGUES AS CD73 INHIBITORS AND THERAPEUTIC USES THEREOF". Page/Page column 29. . Retrieved 2018/12/02.
• 2、 Neres, Jo?o,Labello, Nicholas P.,Somu, Ravindranadh V.,Boshoff, Helena I.,Wilson, Daniel J.,Vannada, Jagadeshwar,Chen, Liqiang,Barry III, Clifton E.,Bennett, Eric M.,Aldrich, Courtney C.. "Inhibition of siderophore biosynthesis in Mycobacterium tuberculosis with nucleoside bisubstrate analogues: Structure-activity relationships of the nucleobase domain of 5′-O-[N-(salicyl)sulfamoyl]adenosine". experimental part. p. 5349 - 5370. Retrieved 2009/07/01.