(6aR,8S,9R,9aR)-tert-butyl 8-(5-(benzyloxymethyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-9-hydroxy-2,2,4,4-tetraisopropyltetrahydro[1,3,5,2,4]trioxadisilocino[7,6-d]pyrrole-7(8H)-carboxylate

Base Information

• Chemical Name: (6aR,8S,9R,9aR)-tert-butyl 8-(5-(benzyloxymethyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-9-hydroxy-2,2,4,4-tetraisopropyltetrahydro[1,3,5,2,4]trioxadisilocino[7,6-d]pyrrole-7(8H)-carboxylate
• CAS No.: 1163713-16-3
• Molecular Formula: C₃₇H₅₈N₄O₈Si₂
• Molecular Weight: 743.061
• Mol file: 1163713-16-3.mol

Synonyms:(6aR,8S,9R,9aR)-tert-butyl 8-(5-(benzyloxymethyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-9-hydroxy-2,2,4,4-tetraisopropyltetrahydro[1,3,5,2,4]trioxadisilocino[7,6-d]pyrrole-7(8H)-carboxylate

Chemical Property of (6aR,8S,9R,9aR)-tert-butyl 8-(5-(benzyloxymethyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-9-hydroxy-2,2,4,4-tetraisopropyltetrahydro[1,3,5,2,4]trioxadisilocino[7,6-d]pyrrole-7(8H)-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6aR,8S,9R,9aR)-tert-butyl 8-(5-(benzyloxymethyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-9-hydroxy-2,2,4,4-tetraisopropyltetrahydro[1,3,5,2,4]trioxadisilocino[7,6-d]pyrrole-7(8H)-carboxylate

There total 23 articles about (6aR,8S,9R,9aR)-tert-butyl 8-(5-(benzyloxymethyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-9-hydroxy-2,2,4,4-tetraisopropyltetrahydro[1,3,5,2,4]trioxadisilocino[7,6-d]pyrrole-7(8H)-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:

C37H56N4O8Si2 → (6aR,8S,9R,9aR)-tert-butyl 8-(5-(benzyloxymethyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-9-hydroxy-2,2,4,4-tetraisopropyltetrahydro[1,3,5,2,4]trioxadisilocino[7,6-d]pyrrole-7(8H)-carboxylate (1163713-16-3)

Guidance literature:

With methanol; sodium tetrahydroborate; at 0 ℃; for 0.5h;

Reference yield:

2,3-O-isopropylidene-L-lyxono-1,4-lactone (152006-17-2) → (6aR,8S,9R,9aR)-tert-butyl 8-(5-(benzyloxymethyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-9-hydroxy-2,2,4,4-tetraisopropyltetrahydro[1,3,5,2,4]trioxadisilocino[7,6-d]pyrrole-7(8H)-carboxylate (1163713-16-3)

Guidance literature:

Multi-step reaction with 12 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: 1H-imidazole / N,N-dimethyl-formamide / 0 - 20 °C

11.1: dimethyl sulfoxide; trifluoroacetic anhydride; triethylamine / dichloromethane / 0.25 h / -70 - 20 °C

12.1: 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; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 11.1: |Swern Oxidation;

Reference yield:

5-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-L-lyxonic acid-1,4-lactone (1044813-00-4) → (6aR,8S,9R,9aR)-tert-butyl 8-(5-(benzyloxymethyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-9-hydroxy-2,2,4,4-tetraisopropyltetrahydro[1,3,5,2,4]trioxadisilocino[7,6-d]pyrrole-7(8H)-carboxylate (1163713-16-3)

Guidance literature:

Multi-step reaction with 11 steps

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

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

3.1: 48 h / 70 °C

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

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

5.2: 17 h / -5 - 5 °C

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

6.2: 0.25 h / -50 - -2 °C

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

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

9.1: 1H-imidazole / N,N-dimethyl-formamide / 0 - 20 °C

10.1: dimethyl sulfoxide; trifluoroacetic anhydride; triethylamine / dichloromethane / 0.25 h / -70 - 20 °C

11.1: 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; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 10.1: |Swern Oxidation;

upstream raw materials:

2,3-O-isopropylidene-L-lyxono-1,4-lactone

5-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-L-lyxonic acid-1,4-lactone

1-amino-1,4-anhydro-N-benzyl-5-O-tertbutyldimethylsilyl-1-deoxy-2,3-O-isopropylidene-D-ribitol

(3aR,4R,6aS)-4-({[(tert-butyl)(dimethyl)silyl]oxy}methyl)tetrahydro-2,2-dimethyl-3aH-[1,3]dioxolo[4,5-c]pyrrole