(-)-(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

Base Information

• Chemical Name: (-)-(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
• CAS No.: 913076-45-6
• Molecular Formula: C₂₆H₃₁NO₅Si
• Molecular Weight: 465.621

Synonyms:(-)-(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

Chemical Property of (-)-(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

Chemical Property:

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Technology Process of (-)-(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

There total 2 articles about (-)-(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 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: 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:

(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)-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:

Multi-step reaction with 2 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

With sodium hydroxide; sodium hydride; In tetrahydrofuran; 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}acetic acid (913076-45-6) → (-)-(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)

Guidance literature:

With oxalyl dichloride; In tetrahydrofuran; for 1h; Heating;

DOI:10.1002/ejoc.200600226

upstream raw materials:

(-)-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

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}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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