(-)-(1R,2S,6R,7R,8R)-5-(3-bromo-2-oxopropyl)-8-tert-butyl(diphenyl)silanyloxy-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one

Base Information

• Chemical Name: (-)-(1R,2S,6R,7R,8R)-5-(3-bromo-2-oxopropyl)-8-tert-butyl(diphenyl)silanyloxy-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one
• CAS No.: 913076-65-0
• Molecular Formula: C₂₇H₃₂BrNO₄Si
• Molecular Weight: 542.545

Synonyms:(-)-(1R,2S,6R,7R,8R)-5-(3-bromo-2-oxopropyl)-8-tert-butyl(diphenyl)silanyloxy-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one

Chemical Property of (-)-(1R,2S,6R,7R,8R)-5-(3-bromo-2-oxopropyl)-8-tert-butyl(diphenyl)silanyloxy-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one

Chemical Property:

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Technology Process of (-)-(1R,2S,6R,7R,8R)-5-(3-bromo-2-oxopropyl)-8-tert-butyl(diphenyl)silanyloxy-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one

There total 5 articles about (-)-(1R,2S,6R,7R,8R)-5-(3-bromo-2-oxopropyl)-8-tert-butyl(diphenyl)silanyloxy-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one 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: 85.0%

(-)-(1R,2S,6R,7R,8R)-8-tert-butyl(diphenyl)silanyloxy-5-(3-diazo-2-oxopropyl)-3-oxa-5-azatricyclo[5.2.1.02,6]decan-4-one (913076-52-5) → (-)-(1R,2S,6R,7R,8R)-5-(3-bromo-2-oxopropyl)-8-tert-butyl(diphenyl)silanyloxy-3-oxa-5-azatricyclo[5.2.1.02,6]decan-4-one (913076-65-0)

Guidance literature:

With hydrogen bromide; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1002/ejoc.200600226

Reference yield:

(1R,2S,6R,7R,8R)-8-(tert-Butyl-diphenyl-silanyloxy)-3-oxa-5-aza-tricyclo[5.2.1.02,6]decan-4-one → (-)-(1R,2S,6R,7R,8R)-5-(3-bromo-2-oxopropyl)-8-tert-butyl(diphenyl)silanyloxy-3-oxa-5-azatricyclo[5.2.1.02,6]decan-4-one (913076-65-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C

1.2: 79 percent / tetrahydrofuran / 12 h / 20 °C

2.1: 95 percent / sodium hydroxide / tetrahydrofuran; H₂O / 12 h / 20 °C

3.1: oxalyl chloride / tetrahydrofuran / 1 h / Heating

4.1: 333 mg / tetrahydrofuran; diethyl ether / 0 - 20 °C

5.1: 85 percent / aq. HBr / CH₂Cl₂ / 1 h / 0 °C

With sodium hydroxide; oxalyl dichloride; hydrogen bromide; sodium hydride; In tetrahydrofuran; diethyl ether; dichloromethane; water;

DOI:10.1002/ejoc.200600226

Reference yield:

(-)-(1R,2S,6R,7R,8R)-2-{8-tert-butyl(diphenyl)silanyloxy-4-oxo-3-oxa-5-azatricyclo[5.2.1.02,6]dec-5-yl}acetyl chloride (913076-47-8) → (-)-(1R,2S,6R,7R,8R)-5-(3-bromo-2-oxopropyl)-8-tert-butyl(diphenyl)silanyloxy-3-oxa-5-azatricyclo[5.2.1.02,6]decan-4-one (913076-65-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 333 mg / tetrahydrofuran; diethyl ether / 0 - 20 °C

2: 85 percent / aq. HBr / CH₂Cl₂ / 1 h / 0 °C

With hydrogen bromide; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1002/ejoc.200600226

upstream raw materials:

(-)-(1R,2S,6R,7R,8R)-8-tert-butyl(diphenyl)silanyloxy-5-(3-diazo-2-oxopropyl)-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one

(-)-(1R,2S,6R,7R,8R)-2-{8-tert-butyl(diphenyl)silanyloxy-4-oxo-3-oxa-5-azatricyclo[5.2.1.0^2,6]dec-5-yl}acetyl chloride

(-)-(1R,2S,6R,7R,8R)-2-{8-tert-butyl(diphenyl)silanyloxy-4-oxo-3-oxa-5-azatricyclo[5.2.1.0^2,6]dec-5-yl}acetic acid

(-)-methyl (1R,2S,6R,7R,8R)-2-{8-tert-butyl(diphenyl)silanyloxy-4-oxo-3-oxa-5-azatricyclo[5.2.1.0^2,6]dec-5-yl}acetate

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