Adenosine, N,N-bis[(1,1-diMethylethoxy)carbonyl]-2',3'-O-(1-Methylethylidene)-

Base Information

• Chemical Name: Adenosine, N,N-bis[(1,1-diMethylethoxy)carbonyl]-2',3'-O-(1-Methylethylidene)-
• CAS No.: 1152172-19-4
• Molecular Formula: C23H33N5O8
• Molecular Weight: 507.53682
• Mol file: 1152172-19-4.mol

Synonyms:Adenosine, N,N-bis[(1,1-diMethylethoxy)carbonyl]-2',3'-O-(1-Methylethylidene)-;tert-butyl N-{9-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]-9H-purin-6-yl}-N-[(tert-butoxy)carbonyl]carbamate;N,N-Bis[(1,1-dimethylethoxy)carbonyl]-2',3'-O-(1-methylethylidene)adenosine

Chemical Property of Adenosine, N,N-bis[(1,1-diMethylethoxy)carbonyl]-2',3'-O-(1-Methylethylidene)-

Chemical Property:

• Boiling Point: 626.3±65.0 °C(Predicted)
• PKA: 14.14±0.10(Predicted)
• PSA: 147.36000
• Density: 1.41±0.1 g/cm3(Predicted)
• LogP: 2.91270

Purity/Quality:

97% ^*data from raw suppliers

N,N-Bis[(1,1-dimethylethoxy)carbonyl]-2'',3''-o-(1-methylethylidene)adenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N,N-Bis[(1,1-dimethylethoxy)carbonyl]-2'',3''-o-(1-methylethylidene)adenosine is used as a reactant in the synthesis of siderophore biosynthesis inhibitors for M. tuberculosis.

Technology Process of Adenosine, N,N-bis[(1,1-diMethylethoxy)carbonyl]-2',3'-O-(1-Methylethylidene)-

There total 6 articles about Adenosine, N,N-bis[(1,1-diMethylethoxy)carbonyl]-2',3'-O-(1-Methylethylidene)- 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%

N6,N6-bis(tert-butoxycarbonyl)-2',3'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl)adenosine → N6,N6-bis(tert-butoxycarbonyl)-2',3'-O-isopropylideneadenosine (1152172-19-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.bmc.2009.07.071

Reference yield: 89.0%

di-tert-butyl dicarbonate (24424-99-5) + 9-((3aR,4R,6R,6aR)-6-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-amine (139301-93-2) → N6,N6-bis(tert-butoxycarbonyl)-2',3'-O-isopropylideneadenosine (1152172-19-4)

Guidance literature:

With dmap; In tetrahydrofuran; for 4h;

Reference yield:

2',3'-isopropylidene adenosine (362-75-4) → N6,N6-bis(tert-butoxycarbonyl)-2',3'-O-isopropylideneadenosine (1152172-19-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 0 - 20 °C / Inert atmosphere

2: dmap; triethylamine / N,N-dimethyl-formamide / 16 h / 0 - 20 °C / Inert atmosphere

3: tetrabutyl ammonium fluoride / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere

With 1H-imidazole; dmap; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1002/anie.201103203

upstream raw materials:

2',3'-isopropylidene adenosine

9-((3aR,4R,6R,6aR)-6-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-amine

adenosine

di-tert-butyl dicarbonate

Downstream raw materials:

N⁶,N⁶-bis(tert-Butoxycarbonyl)-5′-amino-5′-N-(tert-butoxycarbonyl)-5′-N-[(1-benzylquinol-4-on-3-yl)sulfonyl]-5′-deoxy-2′,3′-Oisopropylideneadenosine

C₅₁H₆₁N₉O₁₅

Refernces

• 1、 -. "NOVEL SPIROBICYCLIC INTERMEDIATES". . . Retrieved 2020/12/30.
• 2、 Smit, Cornelis,Bluemer, Julia,Eerland, Martijn F.,Albers, Michael F.,Mueller, Matthias P.,Goody, Roger S.,Itzen, Aymelt,Hedberg, Christian. "Efficient synthesis and applications of peptides containing adenylylated tyrosine residues". supporting information; experimental part. p. 9200 - 9204. Retrieved 2011/11/04.