{(6S,8R)-8-Azido-8-methyl-4-oxo-6-[(R)-1-((1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]dec-4-yl)-propylcarbamoyl]-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-3-yl}-(3-trifluoromethyl-benzyl)-carbamic acid benzyl ester

Base Information

• Chemical Name: {(6S,8R)-8-Azido-8-methyl-4-oxo-6-[(R)-1-((1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]dec-4-yl)-propylcarbamoyl]-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-3-yl}-(3-trifluoromethyl-benzyl)-carbamic acid benzyl ester
• CAS No.: 437761-09-6
• Molecular Formula: C₃₈H₄₃BF₃N₇O₆
• Molecular Weight: 761.609

Synonyms:{(6S,8R)-8-Azido-8-methyl-4-oxo-6-[(R)-1-((1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]dec-4-yl)-propylcarbamoyl]-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-3-yl}-(3-trifluoromethyl-benzyl)-carbamic acid benzyl ester

Chemical Property of {(6S,8R)-8-Azido-8-methyl-4-oxo-6-[(R)-1-((1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]dec-4-yl)-propylcarbamoyl]-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-3-yl}-(3-trifluoromethyl-benzyl)-carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

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Technology Process of {(6S,8R)-8-Azido-8-methyl-4-oxo-6-[(R)-1-((1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]dec-4-yl)-propylcarbamoyl]-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-3-yl}-(3-trifluoromethyl-benzyl)-carbamic acid benzyl ester

There total 8 articles about {(6S,8R)-8-Azido-8-methyl-4-oxo-6-[(R)-1-((1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]dec-4-yl)-propylcarbamoyl]-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-3-yl}-(3-trifluoromethyl-benzyl)-carbamic acid benzyl ester 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:

1-bromomethyl-3-trifluoromethylbenzene (402-23-3) → {(6S,8R)-8-Azido-8-methyl-4-oxo-6-[(R)-1-((1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)-propylcarbamoyl]-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-3-yl}-(3-trifluoromethyl-benzyl)-carbamic acid benzyl ester (437761-09-6)

Guidance literature:

Multi-step reaction with 7 steps

1: NaH; TBAI

2: EDCI; HOAt; NaHCO₃

3: LiHMDS

4: LiHMDS; trisyl azide

5: 100 percent / DMAP / acetonitrile

6: 100 percent / aq. H₂O₂; LiOH

7: EDCI; HOAt

With dmap; lithium hydroxide; 1-hydroxy-7-aza-benzotriazole; 2,4,6-Triisopropylbenzenesulfonyl azide; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium hexamethyldisilazane; In acetonitrile;

DOI:10.1016/S0960-894X(03)00022-2

Reference yield:

(6S)-3-{[(Benzyloxy)carbonyl]amino}-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6-carboxylic acid (227616-77-5) → {(6S,8R)-8-Azido-8-methyl-4-oxo-6-[(R)-1-((1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)-propylcarbamoyl]-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-3-yl}-(3-trifluoromethyl-benzyl)-carbamic acid benzyl ester (437761-09-6)

Guidance literature:

Multi-step reaction with 7 steps

1: NaH; TBAI

2: EDCI; HOAt; NaHCO₃

3: LiHMDS

4: LiHMDS; trisyl azide

5: 100 percent / DMAP / acetonitrile

6: 100 percent / aq. H₂O₂; LiOH

7: EDCI; HOAt

With dmap; lithium hydroxide; 1-hydroxy-7-aza-benzotriazole; 2,4,6-Triisopropylbenzenesulfonyl azide; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium hexamethyldisilazane; In acetonitrile;

DOI:10.1016/S0960-894X(03)00022-2

Reference yield:

(6S)-3-{[(Benzyloxy)carbonyl][3-(trifluoromethyl)benzyl]amino}-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6-carboxylic acid (437761-03-0) → {(6S,8R)-8-Azido-8-methyl-4-oxo-6-[(R)-1-((1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)-propylcarbamoyl]-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-3-yl}-(3-trifluoromethyl-benzyl)-carbamic acid benzyl ester (437761-09-6)

Guidance literature:

Multi-step reaction with 6 steps

1: EDCI; HOAt; NaHCO₃

2: LiHMDS

3: LiHMDS; trisyl azide

4: 100 percent / DMAP / acetonitrile

5: 100 percent / aq. H₂O₂; LiOH

6: EDCI; HOAt

With dmap; lithium hydroxide; 1-hydroxy-7-aza-benzotriazole; 2,4,6-Triisopropylbenzenesulfonyl azide; dihydrogen peroxide; sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium hexamethyldisilazane; In acetonitrile;

DOI:10.1016/S0960-894X(03)00022-2

upstream raw materials:

(1R)-1-aminopropyl boronic acid pinanediol ester

(6S,8R)-8-Azido-3-{[(benzyloxy)carbonyl][3-(trifluoromethyl)benzyl]amino}-8-methyl-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6-carboxylic acid

1-bromomethyl-3-trifluoromethylbenzene

(6S)-3-{[(Benzyloxy)carbonyl]amino}-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6-carboxylic acid

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