(2S,3S,4S,5R)-tert-butyl 2-(5-((benzyloxy)methyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-4-hydroxy-3-((4-methoxybenzyl)oxy)-5-((trityloxy)methyl)pyrrolidine-1-carboxylate

Base Information

Chemical Name:(2S,3S,4S,5R)-tert-butyl 2-(5-((benzyloxy)methyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-4-hydroxy-3-((4-methoxybenzyl)oxy)-5-((trityloxy)methyl)pyrrolidine-1-carboxylate
CAS No.:1163713-17-4
Molecular Formula:C₅₂H₅₄N₄O₈
Molecular Weight:863.023
Hs Code.:

(2S,3S,4S,5R)-tert-butyl 2-(5-((benzyloxy)methyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-4-hydroxy-3-((4-methoxybenzyl)oxy)-5-((trityloxy)methyl)pyrrolidine-1-carboxylate

Synonyms:(2S,3S,4S,5R)-tert-butyl 2-(5-((benzyloxy)methyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-4-hydroxy-3-((4-methoxybenzyl)oxy)-5-((trityloxy)methyl)pyrrolidine-1-carboxylate

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Chemical Property of (2S,3S,4S,5R)-tert-butyl 2-(5-((benzyloxy)methyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-4-hydroxy-3-((4-methoxybenzyl)oxy)-5-((trityloxy)methyl)pyrrolidine-1-carboxylate

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Technology Process of (2S,3S,4S,5R)-tert-butyl 2-(5-((benzyloxy)methyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-4-hydroxy-3-((4-methoxybenzyl)oxy)-5-((trityloxy)methyl)pyrrolidine-1-carboxylate

There total 23 articles about (2S,3S,4S,5R)-tert-butyl 2-(5-((benzyloxy)methyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-4-hydroxy-3-((4-methoxybenzyl)oxy)-5-((trityloxy)methyl)pyrrolidine-1-carboxylate 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:

: C₅₂H₅₂N₄O₈

: 1163713-17-4
(2S,3S,4S,5R)-tert-butyl 2-(5-((benzyloxy)methyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-4-hydroxy-3-((4-methoxybenzyl)oxy)-5-((trityloxy)methyl)pyrrolidine-1-carboxylate

Guidance literature:: With sodium tetrahydroborate; In methanol; at 20 ℃; for 0.5h;
DOI:10.1016/j.bmcl.2009.04.018

Reference yield:

: 152006-17-2
2,3-O-isopropylidene-L-lyxono-1,4-lactone

: 1163713-17-4
(2S,3S,4S,5R)-tert-butyl 2-(5-((benzyloxy)methyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-4-hydroxy-3-((4-methoxybenzyl)oxy)-5-((trityloxy)methyl)pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 13 steps

1.1: 1H-imidazole; dmap / N,N-dimethyl-formamide / 16 h / 0 - 20 °C / Inert atmosphere; Large scale

2.1: sodium tetrahydroborate; methanol / tetrahydrofuran / 22 h / -5 - 20 °C

3.1: pyridine; dmap / 4 h / 0 - 20 °C / Inert atmosphere

4.1: 48 h / 70 °C

5.1: hydrogen; palladium on activated charcoal / ethanol / 5 h / 4137.29 Torr

6.1: N-chloro-succinimide / toluene / 17 - 23 °C

6.2: 17 h / -5 - 5 °C

7.1: n-butyllithium / diethyl ether; hexane / 1.2 h / -70 - -50 °C / Inert atmosphere

7.2: 0.25 h / -50 - -2 °C

8.1: dichloromethane / 0.5 h / 5 - 10 °C

9.1: water; hydrogenchloride / methanol / 25 h / 20 - 35 °C

10.1: dmap; triethylamine / dichloromethane / 22 h / 20 °C

11.1: di(n-butyl)tin oxide / benzene / 1 h / Dean-Stark

11.2: 18 h / Heating

12.1: dimethyl sulfoxide; trifluoroacetic anhydride; triethylamine / dichloromethane / 0.25 h / -70 °C

13.1: sodium tetrahydroborate; methanol / 0.5 h / 0 °C

With pyridine; 1H-imidazole; hydrogenchloride; methanol; dmap; sodium tetrahydroborate; N-chloro-succinimide; n-butyllithium; palladium on activated charcoal; water; hydrogen; di(n-butyl)tin oxide; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; benzene; 12.1: |Swern Oxidation;

Reference yield:

: 2-(tert-butyldimethylsilanoxy)-1-(5-hydroxymethyl-2,2-dimethyl[1,3]dioxolano-4-yl)ethanol

: 1163713-17-4
(2S,3S,4S,5R)-tert-butyl 2-(5-((benzyloxy)methyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-4-hydroxy-3-((4-methoxybenzyl)oxy)-5-((trityloxy)methyl)pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 11 steps

1.1: pyridine; dmap / 4 h / 0 - 20 °C / Inert atmosphere

2.1: 48 h / 70 °C

3.1: hydrogen; palladium on activated charcoal / ethanol / 5 h / 4137.29 Torr

4.1: N-chloro-succinimide / toluene / 17 - 23 °C

4.2: 17 h / -5 - 5 °C

5.1: n-butyllithium / diethyl ether; hexane / 1.2 h / -70 - -50 °C / Inert atmosphere

5.2: 0.25 h / -50 - -2 °C

6.1: dichloromethane / 0.5 h / 5 - 10 °C

7.1: water; hydrogenchloride / methanol / 25 h / 20 - 35 °C

8.1: dmap; triethylamine / dichloromethane / 22 h / 20 °C

9.1: di(n-butyl)tin oxide / benzene / 1 h / Dean-Stark

9.2: 18 h / Heating

10.1: dimethyl sulfoxide; trifluoroacetic anhydride; triethylamine / dichloromethane / 0.25 h / -70 °C

11.1: sodium tetrahydroborate; methanol / 0.5 h / 0 °C

With pyridine; hydrogenchloride; methanol; dmap; sodium tetrahydroborate; N-chloro-succinimide; n-butyllithium; palladium on activated charcoal; water; hydrogen; di(n-butyl)tin oxide; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In methanol; diethyl ether; ethanol; hexane; dichloromethane; toluene; benzene; 10.1: |Swern Oxidation;