(-)-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

Base Information

• Chemical Name: (-)-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
• CAS No.: 913076-43-4
• Molecular Formula: C₂₇H₃₃NO₅Si
• Molecular Weight: 479.648

Synonyms:(-)-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

Chemical Property of (-)-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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Technology Process of (-)-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

There total 1 articles about (-)-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 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: 79.0%

(1R,2S,6R,7R,8R)-8-(tert-Butyl-diphenyl-silanyloxy)-3-oxa-5-aza-tricyclo[5.2.1.02,6]decan-4-one + bromoacetic acid methyl ester (96-32-2) → (-)-methyl (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}acetate (913076-43-4)

Guidance literature:

(1R,2S,6R,7R,8R)-8-(tert-Butyl-diphenyl-silanyloxy)-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]decan-4-one; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 1h;

bromoacetic acid methyl ester; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1002/ejoc.200600226

Reference yield: 95.0%

(-)-methyl (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}acetate (913076-43-4) → (-)-(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}acetic acid (913076-45-6)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 12h;

DOI:10.1002/ejoc.200600226

Reference yield:

(-)-methyl (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}acetate (913076-43-4) → (-)-(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 4 steps

1: 95 percent / sodium hydroxide / tetrahydrofuran; H₂O / 12 h / 20 °C

2: oxalyl chloride / tetrahydrofuran / 1 h / Heating

3: 333 mg / tetrahydrofuran; diethyl ether / 0 - 20 °C

4: 85 percent / aq. HBr / CH₂Cl₂ / 1 h / 0 °C

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

DOI:10.1002/ejoc.200600226

upstream raw materials:

bromoacetic acid methyl ester

Downstream raw materials:

(-)-(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

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

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