6'-O-benzoyl-2'-deoxy-2'-(adenine-9-yl)-5'-deoxy-1',4'-anhydro-D-altritol

Base Information

Chemical Name:6'-O-benzoyl-2'-deoxy-2'-(adenine-9-yl)-5'-deoxy-1',4'-anhydro-D-altritol
CAS No.:289665-53-8
Molecular Formula:C₁₈H₁₉N₅O₄
Molecular Weight:369.38
Hs Code.:

Synonyms:6'-O-benzoyl-2'-deoxy-2'-(adenine-9-yl)-5'-deoxy-1',4'-anhydro-D-altritol

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Chemical Property of 6'-O-benzoyl-2'-deoxy-2'-(adenine-9-yl)-5'-deoxy-1',4'-anhydro-D-altritol

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Technology Process of 6'-O-benzoyl-2'-deoxy-2'-(adenine-9-yl)-5'-deoxy-1',4'-anhydro-D-altritol

There total 7 articles about 6'-O-benzoyl-2'-deoxy-2'-(adenine-9-yl)-5'-deoxy-1',4'-anhydro-D-altritol 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: 51.0%

: 73-24-5,71660-29-2,71660-30-5
7H-purin-6-ylamine

: 289665-51-6
6-O-benzoyl-5-deoxy-1,4:2,3-dianhydro-D-allitol

: 289665-53-8
6'-O-benzoyl-2'-deoxy-2'-(adenine-9-yl)-5'-deoxy-1',4'-anhydro-D-altritol

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 85 ℃; for 48h;
DOI:10.1016/S0957-4166(00)00136-1

Reference yield:

: 62102-11-8
5-deoxy-1,2-O-isopropylidene-3-O-p-tolylsulfonyl-α-D-xylo-hexofuranose

: 289665-53-8
6'-O-benzoyl-2'-deoxy-2'-(adenine-9-yl)-5'-deoxy-1',4'-anhydro-D-altritol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 98 percent / pyridine / 18 h / 20 °C

2.1: TMSOTf / CH₂Cl₂ / 0.5 h / 20 °C

2.2: 53 percent / Et₃SiH / CH₂Cl₂ / 48 h / 0 °C

3.1: 95 percent / t-BuOK / tetrahydrofuran / 0.5 h / -10 °C

4.1: 51 percent / DBU / dimethylformamide / 48 h / 85 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; potassium tert-butylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1.1: Esterification / 2.1: Ring cleavage / 2.2: Reduction / 3.1: Cyclization / 4.1: Addition;
DOI:10.1016/S0957-4166(00)00136-1

Reference yield:

: 43138-33-6
5β-vinyl-4β-tosyl-2α,3α-O-isopropylidene tetrahydrofuran

: 289665-53-8
6'-O-benzoyl-2'-deoxy-2'-(adenine-9-yl)-5'-deoxy-1',4'-anhydro-D-altritol

Guidance literature:: Multi-step reaction with 5 steps

1.1: BH₃*SMe₂ / tetrahydrofuran / 2 h / 20 °C

1.2: 53.5 percent / NaOH; aq. H₂O₂ / methanol; tetrahydrofuran / 2 h / 20 °C

2.1: 98 percent / pyridine / 18 h / 20 °C

3.1: TMSOTf / CH₂Cl₂ / 0.5 h / 20 °C

3.2: 53 percent / Et₃SiH / CH₂Cl₂ / 48 h / 0 °C

4.1: 95 percent / t-BuOK / tetrahydrofuran / 0.5 h / -10 °C

5.1: 51 percent / DBU / dimethylformamide / 48 h / 85 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; dimethylsulfide borane complex; potassium tert-butylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1.1: Reduction / 1.2: Hydrolysis / 2.1: Esterification / 3.1: Ring cleavage / 3.2: Reduction / 4.1: Cyclization / 5.1: Addition;
DOI:10.1016/S0957-4166(00)00136-1