(1S,3R,5S,6S,7R)-6-(tert-Butyl-dimethyl-silanyloxy)-8-(4-methoxy-benzyl)-4-oxa-8-aza-tricyclo[5.1.0.0^3,5]octan-2-one

Base Information

• Chemical Name: (1S,3R,5S,6S,7R)-6-(tert-Butyl-dimethyl-silanyloxy)-8-(4-methoxy-benzyl)-4-oxa-8-aza-tricyclo[5.1.0.0^3,5]octan-2-one
• CAS No.: 627873-29-4
• Molecular Formula: C₂₀H₂₉NO₄Si
• Molecular Weight: 375.54

Synonyms:(1S,3R,5S,6S,7R)-6-(tert-Butyl-dimethyl-silanyloxy)-8-(4-methoxy-benzyl)-4-oxa-8-aza-tricyclo[5.1.0.0^3,5]octan-2-one

Chemical Property of (1S,3R,5S,6S,7R)-6-(tert-Butyl-dimethyl-silanyloxy)-8-(4-methoxy-benzyl)-4-oxa-8-aza-tricyclo[5.1.0.0^3,5]octan-2-one

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Technology Process of (1S,3R,5S,6S,7R)-6-(tert-Butyl-dimethyl-silanyloxy)-8-(4-methoxy-benzyl)-4-oxa-8-aza-tricyclo[5.1.0.0^3,5]octan-2-one

There total 4 articles about (1S,3R,5S,6S,7R)-6-(tert-Butyl-dimethyl-silanyloxy)-8-(4-methoxy-benzyl)-4-oxa-8-aza-tricyclo[5.1.0.0^3,5]octan-2-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: 90.0%

(1S,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyl)-7-aza-bicyclo[4.1.0]hept-3-en-2-one (627873-27-2) → (1S,3R,5S,6S,7R)-6-(tert-Butyl-dimethyl-silanyloxy)-8-(4-methoxy-benzyl)-4-oxa-8-aza-tricyclo[5.1.0.03,5]octan-2-one (627873-29-4)

Guidance literature:

With dihydrogen peroxide; N-benzyl-trimethylammonium hydroxide; In tetrahydrofuran; at 0 ℃;

DOI:10.1021/ol035576i

Reference yield:

(4S,5R)-4,5-O-isopropylidenedioxycyclohex-2-en-1-one (121651-99-8) → (1S,3R,5S,6S,7R)-6-(tert-Butyl-dimethyl-silanyloxy)-8-(4-methoxy-benzyl)-4-oxa-8-aza-tricyclo[5.1.0.03,5]octan-2-one (627873-29-4)

Guidance literature:

Multi-step reaction with 4 steps

1: dmap; iodine / pyridine; diethyl ether / 20 °C

2: 1,10-Phenanthroline; caesium carbonate / toluene / 95 °C

3: N-ethyl-N,N-diisopropylamine; dmap / dichloromethane / 20 °C

4: dihydrogen peroxide; N-benzyl-trimethylammonium hydroxide / tetrahydrofuran / 0 °C

With dmap; 1,10-Phenanthroline; dihydrogen peroxide; iodine; N-benzyl-trimethylammonium hydroxide; caesium carbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; pyridine; diethyl ether; dichloromethane; toluene;

DOI:10.1021/jo402535j

Reference yield:

(3aR,7aS)-6-iodo-2,2-dimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxol-5-one (355401-57-9) → (1S,3R,5S,6S,7R)-6-(tert-Butyl-dimethyl-silanyloxy)-8-(4-methoxy-benzyl)-4-oxa-8-aza-tricyclo[5.1.0.03,5]octan-2-one (627873-29-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 1,10-Phenanthroline; caesium carbonate / toluene / 95 °C

2: N-ethyl-N,N-diisopropylamine; dmap / dichloromethane / 20 °C

3: dihydrogen peroxide; N-benzyl-trimethylammonium hydroxide / tetrahydrofuran / 0 °C

With dmap; 1,10-Phenanthroline; dihydrogen peroxide; N-benzyl-trimethylammonium hydroxide; caesium carbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1021/jo402535j

upstream raw materials:

(1S,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyl)-7-aza-bicyclo[4.1.0]hept-3-en-2-one

(4S,5R)-4,5-O-isopropylidenedioxycyclohex-2-en-1-one

(3aR,7aS)-6-iodo-2,2-dimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxol-5-one

(1aS,3aR,6aS,6bR)-1-(4-Methoxy-benzyl)-5,5-dimethyl-hexahydro-4,6-dioxa-1-aza-cyclopropa[e]inden-2-one

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