(1R,9S,10R,11R,12R)-12-Azido-6-bromo-3,4-dimethoxy-5-methyl-13-(toluene-4-sulfonyl)-13-aza-tricyclo[7.3.1.0^2,7]trideca-2⁽⁷⁾,3,5-triene-10,11-diol

Base Information

• Chemical Name: (1R,9S,10R,11R,12R)-12-Azido-6-bromo-3,4-dimethoxy-5-methyl-13-(toluene-4-sulfonyl)-13-aza-tricyclo[7.3.1.0^2,7]trideca-2⁽⁷⁾,3,5-triene-10,11-diol
• CAS No.: 244126-35-0
• Molecular Formula: C₂₂H₂₅BrN₄O₆S
• Molecular Weight: 553.434
• Mol file: 244126-35-0.mol

Synonyms:(1R,9S,10R,11R,12R)-12-Azido-6-bromo-3,4-dimethoxy-5-methyl-13-(toluene-4-sulfonyl)-13-aza-tricyclo[7.3.1.0^2,7]trideca-2⁽⁷⁾,3,5-triene-10,11-diol

Chemical Property of (1R,9S,10R,11R,12R)-12-Azido-6-bromo-3,4-dimethoxy-5-methyl-13-(toluene-4-sulfonyl)-13-aza-tricyclo[7.3.1.0^2,7]trideca-2⁽⁷⁾,3,5-triene-10,11-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,9S,10R,11R,12R)-12-Azido-6-bromo-3,4-dimethoxy-5-methyl-13-(toluene-4-sulfonyl)-13-aza-tricyclo[7.3.1.0^2,7]trideca-2⁽⁷⁾,3,5-triene-10,11-diol

There total 23 articles about (1R,9S,10R,11R,12R)-12-Azido-6-bromo-3,4-dimethoxy-5-methyl-13-(toluene-4-sulfonyl)-13-aza-tricyclo[7.3.1.0^2,7]trideca-2⁽⁷⁾,3,5-triene-10,11-diol 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: 87.0%

(1R,9S,10R,11R,12R)-12-Azido-11-benzyloxy-6-bromo-3,4-dimethoxy-5-methyl-13-(toluene-4-sulfonyl)-13-aza-tricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-10-ol (244126-34-9) → (1R,9S,10R,11R,12R)-12-Azido-6-bromo-3,4-dimethoxy-5-methyl-13-(toluene-4-sulfonyl)-13-aza-tricyclo[7.3.1.02,7]trideca-2(7),3,5-triene-10,11-diol (244126-35-0)

Guidance literature:

With boron trichloride; In dichloromethane; at -78 - 0 ℃;

DOI:10.1055/s-1999-3161

Reference yield:

toluene-4-sulfonamide (70-55-3) → (1R,9S,10R,11R,12R)-12-Azido-6-bromo-3,4-dimethoxy-5-methyl-13-(toluene-4-sulfonyl)-13-aza-tricyclo[7.3.1.02,7]trideca-2(7),3,5-triene-10,11-diol (244126-35-0)

Guidance literature:

Multi-step reaction with 16 steps

1.1: Cs₂CO₃ / dimethylformamide / 80 °C

2.1: Et₃N / CH₂Cl₂ / 0 °C

3.1: HCl; H₂O / Heating

3.2: 88 percent / SnCl₄ / CH₂Cl₂ / 20 °C

4.1: 91 percent / NaOH / methanol / 20 °C

5.1: 98 percent / imidazole / dimethylformamide / 20 °C

6.1: Mg / tetrahydrofuran / 20 °C

6.2: 91 percent / CuI / tetrahydrofuran / 0 - 20 °C

7.1: 96 percent / DMAP / acetonitrile / 20 °C

8.1: 98 percent / TBAF / tetrahydrofuran / 20 °C

9.1: pyridine / CH₂Cl₂ / 0 °C

10.1: LiN₃ / dimethylformamide / 80 °C

11.1: TMSBr / CH₂Cl₂ / 20 °C

12.1: TFA / CH₂Cl₂ / 20 °C

13.1: 89 percent / PyHBr₃ / CH₂Cl₂ / 20 °C

14.1: 88 percent / TFA; H₂O / 70 °C

15.1: 89 percent / K₂CO₃ / acetone / Heating

16.1: 87 percent / BCl₃ / CH₂Cl₂ / -78 - 0 °C

With pyridine; 1H-imidazole; hydrogenchloride; dmap; sodium hydroxide; lithium azide; trimethylsilyl bromide; tetrabutyl ammonium fluoride; water; boron trichloride; potassium carbonate; caesium carbonate; magnesium; pyridinium hydrobromide perbromide; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile; 1.1: Ring cleavage / 2.1: Substitution / 3.1: Substitution / 3.2: Isomerization / 4.1: Cyclization / 5.1: Substitution / 6.1: Metallation / 6.2: Substitution / 7.1: Substitution / 8.1: Substitution / 9.1: Substitution / 10.1: Substitution / 11.1: Substitution / 12.1: Substitution / 13.1: Bromination / 14.1: Cyclization / 15.1: Methylation / 16.1: Substitution;

DOI:10.1055/s-1999-3161

Reference yield:

3-methylbenzene-1,2-diol (488-17-5) → (1R,9S,10R,11R,12R)-12-Azido-6-bromo-3,4-dimethoxy-5-methyl-13-(toluene-4-sulfonyl)-13-aza-tricyclo[7.3.1.02,7]trideca-2(7),3,5-triene-10,11-diol (244126-35-0)

Guidance literature:

Multi-step reaction with 16 steps

1.1: 83 percent / TEA / CH₂Cl₂ / 0 °C

2.1: 97 percent / Br₂; AcOH / CH₂Cl₂ / 20 °C

3.1: 96 percent / K₂CO₃ / acetone / Heating

4.1: 97 percent / H₂O; NaOH / ethanol / Heating

5.1: 97 percent / (i-Pr)2NEt / CH₂Cl₂ / 20 °C

6.1: Mg / tetrahydrofuran / 20 °C

6.2: 91 percent / CuI / tetrahydrofuran / 0 - 20 °C

7.1: 96 percent / DMAP / acetonitrile / 20 °C

8.1: 98 percent / TBAF / tetrahydrofuran / 20 °C

9.1: pyridine / CH₂Cl₂ / 0 °C

10.1: LiN₃ / dimethylformamide / 80 °C

11.1: TMSBr / CH₂Cl₂ / 20 °C

12.1: TFA / CH₂Cl₂ / 20 °C

13.1: 89 percent / PyHBr₃ / CH₂Cl₂ / 20 °C

14.1: 88 percent / TFA; H₂O / 70 °C

15.1: 89 percent / K₂CO₃ / acetone / Heating

16.1: 87 percent / BCl₃ / CH₂Cl₂ / -78 - 0 °C

With pyridine; dmap; sodium hydroxide; lithium azide; trimethylsilyl bromide; TEA; tetrabutyl ammonium fluoride; water; bromine; boron trichloride; potassium carbonate; magnesium; acetic acid; pyridinium hydrobromide perbromide; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile; 1.1: Tosylation / 2.1: Bromination / 3.1: Methylation / 4.1: Hydrolysis / 5.1: Etherification / 6.1: Metallation / 6.2: Substitution / 7.1: Substitution / 8.1: Substitution / 9.1: Substitution / 10.1: Substitution / 11.1: Substitution / 12.1: Substitution / 13.1: Bromination / 14.1: Cyclization / 15.1: Methylation / 16.1: Substitution;

DOI:10.1055/s-1999-3161

upstream raw materials:

(1R,9S,10R,11R,12R)-12-Azido-11-benzyloxy-6-bromo-3,4-dimethoxy-5-methyl-13-(toluene-4-sulfonyl)-13-aza-tricyclo[7.3.1.0^2,7]trideca-2⁽⁷⁾,3,5-trien-10-ol

toluene-4-sulfonamide

3-methylbenzene-1,2-diol

5-bromo-2-methoxy-3-methyl-phenol

Downstream raw materials:

(1R,9S,10R,11R,12R)-12-Amino-6-bromo-3,4-dimethoxy-5-methyl-13-(toluene-4-sulfonyl)-13-aza-tricyclo[7.3.1.0^2,7]trideca-2⁽⁷⁾,3,5-triene-10,11-diol

C₂₄H₂₅BrN₂O₇S