(1S,2R,6S,7S,8S)-8-(tert-Butyl-diphenyl-silanyloxy)-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]decan-4-one

Base Information

• Chemical Name: (1S,2R,6S,7S,8S)-8-(tert-Butyl-diphenyl-silanyloxy)-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]decan-4-one
• CAS No.: 188123-40-2
• Molecular Formula: C₂₄H₂₉NO₃Si
• Molecular Weight: 407.585

Synonyms:(1S,2R,6S,7S,8S)-8-(tert-Butyl-diphenyl-silanyloxy)-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]decan-4-one

Chemical Property of (1S,2R,6S,7S,8S)-8-(tert-Butyl-diphenyl-silanyloxy)-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]decan-4-one

Chemical Property:

Purity/Quality:

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Technology Process of (1S,2R,6S,7S,8S)-8-(tert-Butyl-diphenyl-silanyloxy)-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]decan-4-one

There total 8 articles about (1S,2R,6S,7S,8S)-8-(tert-Butyl-diphenyl-silanyloxy)-3-oxa-5-aza-tricyclo[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: 99.0%

tert-butylchlorodiphenylsilane (58479-61-1) + (1S,3S,7S,8S,10R)-10-Hydroxy-4-oxa-6-aza-tricyclo[5.2.1.03,8]decan-5-one (188123-38-8) → (1S,2R,6S,7S,8S)-8-(tert-Butyl-diphenyl-silanyloxy)-3-oxa-5-aza-tricyclo[5.2.1.02,6]decan-4-one (188123-40-2)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; for 1.5h; Ambient temperature;

DOI:10.1016/S0040-4039(96)02402-1

Reference yield: 85.0%

tert-butylchlorodiphenylsilane (58479-61-1) + (1S,2R,6S,7S,8S)-8-Hydroxy-3-oxa-5-aza-tricyclo[5.2.1.02,6]decan-4-one (188123-39-9) → (1S,2R,6S,7S,8S)-8-(tert-Butyl-diphenyl-silanyloxy)-3-oxa-5-aza-tricyclo[5.2.1.02,6]decan-4-one (188123-40-2)

Guidance literature:

With n-butyllithium; for 3h; -78 deg C up to RT;

DOI:10.1016/S0040-4039(96)02402-1

Reference yield:

(+)-(1S,2R,6S,7R)-3-oxa-5-azatricyclo[5.2.1.02,6]dec-8-en-4-one (139240-75-8) → (1S,2R,6S,7S,8S)-8-(tert-Butyl-diphenyl-silanyloxy)-3-oxa-5-aza-tricyclo[5.2.1.02,6]decan-4-one (188123-40-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 100 percent / Et₃N, DMAP / tetrahydrofuran / 1 h / Ambient temperature

2: 95 percent / tetrahydrofuran / 0.17 h / -78 °C

3: 63 percent / I₂ / CH₂Cl₂ / 7 h / Ambient temperature

4: 81 percent / AIBN, Bu₃SnH / benzene / 7 h / Heating

5: 100 percent / Cs₂CO₃ / methanol / 1.5 h / Ambient temperature

6: 99 percent / NaH / dimethylformamide / 1.5 h / Ambient temperature

With dmap; 2,2'-azobis(isobutyronitrile); iodine; tri-n-butyl-tin hydride; sodium hydride; caesium carbonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4039(96)02402-1

upstream raw materials:

tert-butylchlorodiphenylsilane

(1S,3S,7S,8S,10R)-10-Hydroxy-4-oxa-6-aza-tricyclo[5.2.1.0^3,8]decan-5-one

(1S,2R,6S,7S,8S)-8-Hydroxy-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]decan-4-one

(+)-(1S,2R,6S,7R)-3-oxa-5-azatricyclo[5.2.1.0^2,6]dec-8-en-4-one

Downstream raw materials:

(1S,2R,6S,7S,8S)-8-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-2-methyl-butyryl)-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]decan-4-one

(1S,2R,6S,7S,8S)-8-(tert-Butyl-diphenyl-silanyloxy)-5-((R)-2-methyl-pent-4-enoyl)-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]decan-4-one

(1S,2R,6S,7S,8S)-8-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-3-methyl-hexanoyl)-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]decan-4-one

(1S,2R,6S,7S,8S)-8-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-3-methyl-heptanoyl)-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]decan-4-one

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