(3R,4aS,7R,8S)-8-(4-Bromo-benzyloxymethyl)-3-[(S)-(tert-butyl-dimethyl-silanyloxy)-(2,6-dimethoxy-pyrimidin-4-yl)-methyl]-7-methyl-hexahydro-pyrido[1,2-c]pyrimidine-1,6-dione

Base Information

• Chemical Name: (3R,4aS,7R,8S)-8-(4-Bromo-benzyloxymethyl)-3-[(S)-(tert-butyl-dimethyl-silanyloxy)-(2,6-dimethoxy-pyrimidin-4-yl)-methyl]-7-methyl-hexahydro-pyrido[1,2-c]pyrimidine-1,6-dione
• CAS No.: 434309-02-1
• Molecular Formula: C₃₀H₄₃BrN₄O₆Si
• Molecular Weight: 663.684

Synonyms:(3R,4aS,7R,8S)-8-(4-Bromo-benzyloxymethyl)-3-[(S)-(tert-butyl-dimethyl-silanyloxy)-(2,6-dimethoxy-pyrimidin-4-yl)-methyl]-7-methyl-hexahydro-pyrido[1,2-c]pyrimidine-1,6-dione

Chemical Property of (3R,4aS,7R,8S)-8-(4-Bromo-benzyloxymethyl)-3-[(S)-(tert-butyl-dimethyl-silanyloxy)-(2,6-dimethoxy-pyrimidin-4-yl)-methyl]-7-methyl-hexahydro-pyrido[1,2-c]pyrimidine-1,6-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of (3R,4aS,7R,8S)-8-(4-Bromo-benzyloxymethyl)-3-[(S)-(tert-butyl-dimethyl-silanyloxy)-(2,6-dimethoxy-pyrimidin-4-yl)-methyl]-7-methyl-hexahydro-pyrido[1,2-c]pyrimidine-1,6-dione

There total 23 articles about (3R,4aS,7R,8S)-8-(4-Bromo-benzyloxymethyl)-3-[(S)-(tert-butyl-dimethyl-silanyloxy)-(2,6-dimethoxy-pyrimidin-4-yl)-methyl]-7-methyl-hexahydro-pyrido[1,2-c]pyrimidine-1,6-dione 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:

(3R,4aS,7R,8S)-8-(4-Bromo-benzyloxymethyl)-3-[(S)-(tert-butyl-dimethyl-silanyloxy)-(2,6-dimethoxy-pyrimidin-4-yl)-methyl]-6-hydroxy-7-methyl-octahydro-pyrido[1,2-c]pyrimidin-1-one → (3R,4aS,7R,8S)-8-(4-Bromo-benzyloxymethyl)-3-[(S)-(tert-butyl-dimethyl-silanyloxy)-(2,6-dimethoxy-pyrimidin-4-yl)-methyl]-7-methyl-hexahydro-pyrido[1,2-c]pyrimidine-1,6-dione (434309-02-1)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 24 ℃; for 1.5h;

DOI:10.1021/jo0486387

Reference yield:

2-(4-bromobenzyloxy)ethanol (400837-92-5) → (3R,4aS,7R,8S)-8-(4-Bromo-benzyloxymethyl)-3-[(S)-(tert-butyl-dimethyl-silanyloxy)-(2,6-dimethoxy-pyrimidin-4-yl)-methyl]-7-methyl-hexahydro-pyrido[1,2-c]pyrimidine-1,6-dione (434309-02-1)

Guidance literature:

Multi-step reaction with 13 steps

1.1: Dess-Martin periodinane / CH₂Cl₂ / 2 h / 24 °C

2.1: n-BuLi; t-BuOK; (+)-(Ipc)2BOMe / BF₃*OEt₂ / tetrahydrofuran; hexane; diethyl ether / 5 h / -78 °C

2.2: 45 percent / aq. NaOH; H₂O₂ / tetrahydrofuran; hexane; diethyl ether / 1 h / Heating

3.1: pyridine; DMAP / CH₂Cl₂ / 16 h / 24 °C

4.1: NaN₃ / dimethylformamide / 16 h / 85 °C

5.1: 7.0 mg / PPh₃ / tetrahydrofuran; H₂O / 4 h / 55 °C

6.1: Na₂CO₃ / methanol / 17 h / 24 - 60 °C

7.1: m-CPBA / CH₂Cl₂ / 2 h / 24 °C

8.1: 25.6 mg / NH₂OH*HCl / methanol / 2 h / 0 °C

9.1: 60 percent / methanol / 5 h / Heating

10.1: toluene / 72 h / 96 °C

10.2: NH₄Cl; Zn / tetrahydrofuran; H₂O / 8 h / 65 °C

11.1: 301 mg / HCl / methanol

12.1: carbonyldiimidazole / CH₂Cl₂ / 7 h / 40 °C

12.2: K₂CO₃ / methanol / 1 h / 60 °C

13.1: Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 24 °C

With pyridine; hydrogenchloride; dmap; n-butyllithium; sodium azide; hydroxylamine hydrochloride; potassium tert-butylate; sodium carbonate; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; (+)-B-methoxydiisocamphenylborane; 1,1'-carbonyldiimidazole; boron trifluoride diethyl etherate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 1.1: Dess-Martin oxidation / 13.1: Dess-Martin oxidation;

DOI:10.1021/jo0486387

Reference yield:

1-bromomethyl-4-bromobenzene (589-15-1) → (3R,4aS,7R,8S)-8-(4-Bromo-benzyloxymethyl)-3-[(S)-(tert-butyl-dimethyl-silanyloxy)-(2,6-dimethoxy-pyrimidin-4-yl)-methyl]-7-methyl-hexahydro-pyrido[1,2-c]pyrimidine-1,6-dione (434309-02-1)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 65 percent / NaH / tetrahydrofuran / 12 h / Heating

2.1: Dess-Martin periodinane / CH₂Cl₂ / 2 h / 24 °C

3.1: n-BuLi; t-BuOK; (+)-(Ipc)2BOMe / BF₃*OEt₂ / tetrahydrofuran; hexane; diethyl ether / 5 h / -78 °C

3.2: 45 percent / aq. NaOH; H₂O₂ / tetrahydrofuran; hexane; diethyl ether / 1 h / Heating

4.1: pyridine; DMAP / CH₂Cl₂ / 16 h / 24 °C

5.1: NaN₃ / dimethylformamide / 16 h / 85 °C

6.1: 7.0 mg / PPh₃ / tetrahydrofuran; H₂O / 4 h / 55 °C

7.1: Na₂CO₃ / methanol / 17 h / 24 - 60 °C

8.1: m-CPBA / CH₂Cl₂ / 2 h / 24 °C

9.1: 25.6 mg / NH₂OH*HCl / methanol / 2 h / 0 °C

10.1: 60 percent / methanol / 5 h / Heating

11.1: toluene / 72 h / 96 °C

11.2: NH₄Cl; Zn / tetrahydrofuran; H₂O / 8 h / 65 °C

12.1: 301 mg / HCl / methanol

13.1: carbonyldiimidazole / CH₂Cl₂ / 7 h / 40 °C

13.2: K₂CO₃ / methanol / 1 h / 60 °C

14.1: Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 24 °C

With pyridine; hydrogenchloride; dmap; n-butyllithium; sodium azide; hydroxylamine hydrochloride; potassium tert-butylate; sodium hydride; sodium carbonate; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; (+)-B-methoxydiisocamphenylborane; 1,1'-carbonyldiimidazole; boron trifluoride diethyl etherate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 2.1: Dess-Martin oxidation / 14.1: Dess-Martin oxidation;

DOI:10.1021/jo0486387

upstream raw materials:

2-(4-bromobenzyloxy)ethanol

1-bromomethyl-4-bromobenzene

4-bromo-2,6-dimethoxy-pyrimidine

2-((4-bromobenzyl)oxy)acetaldehyde

Downstream raw materials:

cylindrospermopsin

(3R,4aS,6S,7R,8S)-8-(4-Bromo-benzyloxymethyl)-3-[(S)-(tert-butyl-dimethyl-silanyloxy)-(2,6-dimethoxy-pyrimidin-4-yl)-methyl]-6-hydroxy-7-methyl-octahydro-pyrido[1,2-c]pyrimidin-1-one

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