(2S,3S,3aR,6S,7R,7aR)-7-azido-2-(2',4'-dimethoxypyrimidin-5'-yl)-6-methoxy-3-(p-methoxybenzyloxy)-hexahydro-2H-furo[3,2-b]pyran

Base Information

Chemical Name:(2S,3S,3aR,6S,7R,7aR)-7-azido-2-(2',4'-dimethoxypyrimidin-5'-yl)-6-methoxy-3-(p-methoxybenzyloxy)-hexahydro-2H-furo[3,2-b]pyran
CAS No.:630104-54-0
Molecular Formula:C₂₂H₂₇N₅O₇
Molecular Weight:473.486
Hs Code.:

Synonyms:(2S,3S,3aR,6S,7R,7aR)-7-azido-2-(2',4'-dimethoxypyrimidin-5'-yl)-6-methoxy-3-(p-methoxybenzyloxy)-hexahydro-2H-furo[3,2-b]pyran

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Chemical Property of (2S,3S,3aR,6S,7R,7aR)-7-azido-2-(2',4'-dimethoxypyrimidin-5'-yl)-6-methoxy-3-(p-methoxybenzyloxy)-hexahydro-2H-furo[3,2-b]pyran

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Technology Process of (2S,3S,3aR,6S,7R,7aR)-7-azido-2-(2',4'-dimethoxypyrimidin-5'-yl)-6-methoxy-3-(p-methoxybenzyloxy)-hexahydro-2H-furo[3,2-b]pyran

There total 21 articles about (2S,3S,3aR,6S,7R,7aR)-7-azido-2-(2',4'-dimethoxypyrimidin-5'-yl)-6-methoxy-3-(p-methoxybenzyloxy)-hexahydro-2H-furo[3,2-b]pyran 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:

: (2S,3S,3aR,6S,7R,7aR)-7-Azido-2-(2,4-dimethoxy-pyrimidin-5-yl)-3-(4-methoxy-benzyloxy)-hexahydro-furo[3,2-b]pyran-6-ol

: 74-88-4
methyl iodide

: 630104-54-0
(2S,3S,3aR,6S,7R,7aR)-7-azido-2-(2',4'-dimethoxypyrimidin-5'-yl)-6-methoxy-3-(p-methoxybenzyloxy)-hexahydro-2H-furo[3,2-b]pyran

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 2h;
DOI:10.1021/ol030095k

Reference yield:

: 630104-50-6
(2S,3S,4R,5R)-5-(2',4'-dimethoxypyrimidin-5'-yl)-4-(4'-methoxybenzyloxy)-2-vinyltetrahydrofuran-3-ol

: 630104-54-0
(2S,3S,3aR,6S,7R,7aR)-7-azido-2-(2',4'-dimethoxypyrimidin-5'-yl)-6-methoxy-3-(p-methoxybenzyloxy)-hexahydro-2H-furo[3,2-b]pyran

Guidance literature:: Multi-step reaction with 8 steps

1: 91 percent / sodium hydride / dimethylformamide / 0 °C

2: 94 percent / first generation Grubbs catalyst / CH₂Cl₂ / 5 h / Heating

3: NBS / tetrahydrofuran; H₂O / 1.5 h / 20 °C

4: NaOH / tetrahydrofuran; H₂O / 1 h / Heating

5: 500 mg / sodium azide / 2-methoxy-ethanol / 1 h / Heating

6: Dess-Martin periodinane / CH₂Cl₂ / 4 h / 20 °C

7: NaBH₄ / methanol / 1 h

8: 800 mg / NaH / dimethylformamide / 0 °C

With sodium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; sodium azide; sodium hydride; Dess-Martin periodane; Grubbs catalyst first generation; In tetrahydrofuran; methanol; dichloromethane; 2-methoxy-ethanol; water; N,N-dimethyl-formamide; 2: Grubbs metathesis / 6: Dess-Martin reaction;
DOI:10.1016/j.tet.2005.12.066

Reference yield:

: 630104-51-7
(2S,3S,4R,5R)-4-allyloxy-2-(2',4'-dimethoxypyrimidin-5'-yl)-3-(p-methoxybenzyloxy)-5-vinyltetrahydrofuran

: 630104-54-0
(2S,3S,3aR,6S,7R,7aR)-7-azido-2-(2',4'-dimethoxypyrimidin-5'-yl)-6-methoxy-3-(p-methoxybenzyloxy)-hexahydro-2H-furo[3,2-b]pyran

Guidance literature:: Multi-step reaction with 7 steps

1: 94 percent / first generation Grubbs catalyst / CH₂Cl₂ / 5 h / Heating

2: NBS / tetrahydrofuran; H₂O / 1.5 h / 20 °C

3: NaOH / tetrahydrofuran; H₂O / 1 h / Heating

4: 500 mg / sodium azide / 2-methoxy-ethanol / 1 h / Heating

5: Dess-Martin periodinane / CH₂Cl₂ / 4 h / 20 °C

6: NaBH₄ / methanol / 1 h

7: 800 mg / NaH / dimethylformamide / 0 °C

With sodium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; sodium azide; sodium hydride; Dess-Martin periodane; Grubbs catalyst first generation; In tetrahydrofuran; methanol; dichloromethane; 2-methoxy-ethanol; water; N,N-dimethyl-formamide; 1: Grubbs metathesis / 5: Dess-Martin reaction;
DOI:10.1016/j.tet.2005.12.066