(1S,5R,6R)-4-{2-Bromo-5-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-benzyl}-6-hydroxymethyl-2-oxo-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid benzyl ester

Base Information

• Chemical Name: (1S,5R,6R)-4-{2-Bromo-5-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-benzyl}-6-hydroxymethyl-2-oxo-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid benzyl ester
• CAS No.: 115288-78-3
• Molecular Formula: C₃₀H₄₁BrN₂O₅Si
• Molecular Weight: 617.655

Synonyms:(1S,5R,6R)-4-{2-Bromo-5-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-benzyl}-6-hydroxymethyl-2-oxo-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid benzyl ester

Chemical Property of (1S,5R,6R)-4-{2-Bromo-5-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-benzyl}-6-hydroxymethyl-2-oxo-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,5R,6R)-4-{2-Bromo-5-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-benzyl}-6-hydroxymethyl-2-oxo-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid benzyl ester

There total 13 articles about (1S,5R,6R)-4-{2-Bromo-5-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-benzyl}-6-hydroxymethyl-2-oxo-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic 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: 78.0%

(1S,5R,6R)-4-{3-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-benzyl}-6-hydroxymethyl-2-oxo-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid benzyl ester (115288-77-2) → (1S,5R,6R)-4-{2-Bromo-5-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-benzyl}-6-hydroxymethyl-2-oxo-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid benzyl ester (115288-78-3)

Guidance literature:

With bromine; In dichloromethane; Ambient temperature;

DOI:10.1021/ja00223a052

Reference yield:

chlorodimethyl(1,1,2-trimethylpropyl)silane (67373-56-2) → (1S,5R,6R)-4-{2-Bromo-5-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-benzyl}-6-hydroxymethyl-2-oxo-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid benzyl ester (115288-78-3)

Guidance literature:

Multi-step reaction with 10 steps

1: i-Pr₂NEt / 1,2-dichloro-ethane / 70 °C

2: t-BuOK / 2-methyl-propan-2-ol; tetrahydrofuran / -78 °C

3: NH₃ / methanol / Ambient temperature

4: 82 percent / Et₃N, DMAP / CH₂Cl₂ / 24 h / -20 °C

5: NaBH₄ / methanol; CH₂Cl₂ / -20 °C

6: HgCl₂, CSA / acetonitrile; H₂O / 0.33 h / 40 °C

7: 59 percent / NaBH₄ / methanol; CH₂Cl₂ / 0 °C

8: H₂ / Ra-Ni (W₂) / ethanol / 1.5 h / 100 °C / 103430 Torr

9: NaHCO₃ / ethanol / Ambient temperature

10: 78 percent / Br₂ / CH₂Cl₂ / Ambient temperature

With dmap; sodium tetrahydroborate; camphor-10-sulfonic acid; potassium tert-butylate; ammonia; hydrogen; bromine; sodium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; mercury dichloride; Ra-Ni (W₂); In tetrahydrofuran; methanol; ethanol; dichloromethane; water; 1,2-dichloro-ethane; acetonitrile; tert-butyl alcohol;

DOI:10.1021/ja00223a052

Reference yield:

meta-hydroxybenzaldehyde (100-83-4) → (1S,5R,6R)-4-{2-Bromo-5-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-benzyl}-6-hydroxymethyl-2-oxo-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid benzyl ester (115288-78-3)

Guidance literature:

Multi-step reaction with 10 steps

1: i-Pr₂NEt / 1,2-dichloro-ethane / 70 °C

2: t-BuOK / 2-methyl-propan-2-ol; tetrahydrofuran / -78 °C

3: NH₃ / methanol / Ambient temperature

4: 82 percent / Et₃N, DMAP / CH₂Cl₂ / 24 h / -20 °C

5: NaBH₄ / methanol; CH₂Cl₂ / -20 °C

6: HgCl₂, CSA / acetonitrile; H₂O / 0.33 h / 40 °C

7: 59 percent / NaBH₄ / methanol; CH₂Cl₂ / 0 °C

8: H₂ / Ra-Ni (W₂) / ethanol / 1.5 h / 100 °C / 103430 Torr

9: NaHCO₃ / ethanol / Ambient temperature

10: 78 percent / Br₂ / CH₂Cl₂ / Ambient temperature

With dmap; sodium tetrahydroborate; camphor-10-sulfonic acid; potassium tert-butylate; ammonia; hydrogen; bromine; sodium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; mercury dichloride; Ra-Ni (W₂); In tetrahydrofuran; methanol; ethanol; dichloromethane; water; 1,2-dichloro-ethane; acetonitrile; tert-butyl alcohol;

DOI:10.1021/ja00223a052

upstream raw materials:

(1S,5R,6R)-4-{3-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-benzyl}-6-hydroxymethyl-2-oxo-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid benzyl ester

chlorodimethyl(1,1,2-trimethylpropyl)silane

meta-hydroxybenzaldehyde

3-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-benzaldehyde

Downstream raw materials:

quinocarcin

C₁₉H₂₃N₃O₄

(2R,3R,5S)-3-Acetoxymethyl-2-[(S)-2-(2-bromo-5-hydroxy-phenyl)-1-tert-butoxycarbonylamino-ethyl]-5-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester

C₂₈H₂₉N₃O₇

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