N-(Benzyloxycarbonyl)-5(R)-<(benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-(9-guaninylmethyl)pyrrolidine

Base Information

Chemical Name:N-(Benzyloxycarbonyl)-5(R)-<(benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-(9-guaninylmethyl)pyrrolidine
CAS No.:162895-77-4
Molecular Formula:C₄₀H₄₀N₆O₆
Molecular Weight:700.794
Hs Code.:

Synonyms:N-(Benzyloxycarbonyl)-5(R)-<(benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-(9-guaninylmethyl)pyrrolidine

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Chemical Property of N-(Benzyloxycarbonyl)-5(R)-<(benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-(9-guaninylmethyl)pyrrolidine

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Technology Process of N-(Benzyloxycarbonyl)-5(R)-<(benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-(9-guaninylmethyl)pyrrolidine

There total 8 articles about N-(Benzyloxycarbonyl)-5(R)-<(benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-(9-guaninylmethyl)pyrrolidine 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: 49.5%

: 162895-76-3
N-(Benzyloxycarbonyl)-5(R)-<(benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-<(2-amino-6-chloropurin-9-yl)methyl>pyrrolidine

: 162895-77-4
N-(Benzyloxycarbonyl)-5(R)-<(benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-(9-guaninylmethyl)pyrrolidine

Guidance literature:: With sodium methylate; 2-hydroxyethanethiol; In methanol; for 9h; Heating;
DOI:10.1021/jo00111a007

Reference yield:

: 132295-44-4
2,5-anhydro-2,5-imino-D-glucitol

: 162895-77-4
N-(Benzyloxycarbonyl)-5(R)-<(benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-(9-guaninylmethyl)pyrrolidine

Guidance literature:: Multi-step reaction with 7 steps

1: 92 percent / 10percent aq. NaHCO₃ / toluene / 1 h

2: 88 percent / NaH, KI / dimethylformamide / 12 h / Ambient temperature

3: 90 percent / aq. KOH / ethane-1,2-diol / 24 h / 100 °C

4: 88 percent / Et₃N / CH₂Cl₂ / 1 h / 5 °C

5: 87.8 percent / pyridine / 18 h / Ambient temperature

6: 50 percent / K₂CO₃ / dimethylformamide / 18 h / 80 °C

7: 49.5 percent / 2-mercaptoethanol, NaOMe / methanol / 9 h / Heating

With pyridine; potassium hydroxide; sodium methylate; sodium hydride; sodium hydrogencarbonate; potassium carbonate; triethylamine; 2-hydroxyethanethiol; potassium iodide; In methanol; dichloromethane; ethylene glycol; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00111a007

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 162895-77-4
N-(Benzyloxycarbonyl)-5(R)-<(benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-(9-guaninylmethyl)pyrrolidine

Guidance literature:: Multi-step reaction with 4 steps

1: 88 percent / Et₃N / CH₂Cl₂ / 1 h / 5 °C

2: 87.8 percent / pyridine / 18 h / Ambient temperature

3: 50 percent / K₂CO₃ / dimethylformamide / 18 h / 80 °C

4: 49.5 percent / 2-mercaptoethanol, NaOMe / methanol / 9 h / Heating

With pyridine; sodium methylate; potassium carbonate; triethylamine; 2-hydroxyethanethiol; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00111a007