(R)-2-[(1S,2R,5S,6R)-2,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-oxa-bicyclo[4.1.0]hept-2-yl]-3-[[3-((1S,2S,4aR,6S,8aS)-2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-3-oxo-propionyl]-(4-methoxy-benzyloxy)-amino]-propionic acid

Base Information

Chemical Name:(R)-2-[(1S,2R,5S,6R)-2,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-oxa-bicyclo[4.1.0]hept-2-yl]-3-[[3-((1S,2S,4aR,6S,8aS)-2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-3-oxo-propionyl]-(4-methoxy-benzyloxy)-amino]-propionic acid
CAS No.:872472-48-5
Molecular Formula:C₄₄H₇₁NO₉Si₂
Molecular Weight:814.22
Hs Code.:

(R)-2-[(1S,2R,5S,6R)-2,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-oxa-bicyclo[4.1.0]hept-2-yl]-3-[[3-((1S,2S,4aR,6S,8aS)-2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-3-oxo-propionyl]-(4-methoxy-benzyloxy)-amino]-propionic acid

Synonyms:(R)-2-[(1S,2R,5S,6R)-2,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-oxa-bicyclo[4.1.0]hept-2-yl]-3-[[3-((1S,2S,4aR,6S,8aS)-2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-3-oxo-propionyl]-(4-methoxy-benzyloxy)-amino]-propionic acid

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Chemical Property of (R)-2-[(1S,2R,5S,6R)-2,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-oxa-bicyclo[4.1.0]hept-2-yl]-3-[[3-((1S,2S,4aR,6S,8aS)-2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-3-oxo-propionyl]-(4-methoxy-benzyloxy)-amino]-propionic acid

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Technology Process of (R)-2-[(1S,2R,5S,6R)-2,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-oxa-bicyclo[4.1.0]hept-2-yl]-3-[[3-((1S,2S,4aR,6S,8aS)-2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-3-oxo-propionyl]-(4-methoxy-benzyloxy)-amino]-propionic acid

There total 18 articles about (R)-2-[(1S,2R,5S,6R)-2,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-oxa-bicyclo[4.1.0]hept-2-yl]-3-[[3-((1S,2S,4aR,6S,8aS)-2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-3-oxo-propionyl]-(4-methoxy-benzyloxy)-amino]-propionic 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: 85.0%

: 872472-47-4
(R)-2-[(1S,2R,5S,6R)-2,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-oxa-bicyclo[4.1.0]hept-2-yl]-3-[[3-((1S,2S,4aR,6S,8aS)-2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-3-oxo-propionyl]-(4-methoxy-benzyloxy)-amino]-propionic acid allyl ester

: 872472-48-5
(R)-2-[(1S,2R,5S,6R)-2,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-oxa-bicyclo[4.1.0]hept-2-yl]-3-[[3-((1S,2S,4aR,6S,8aS)-2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-3-oxo-propionyl]-(4-methoxy-benzyloxy)-amino]-propionic acid

Guidance literature:: With pyrrolidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In dichloromethane;
DOI:10.1002/anie.200502015

Reference yield:

: 872472-49-6
(S)-4-Methyl-hept-6-ynal

: 872472-48-5
(R)-2-[(1S,2R,5S,6R)-2,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-oxa-bicyclo[4.1.0]hept-2-yl]-3-[[3-((1S,2S,4aR,6S,8aS)-2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-3-oxo-propionyl]-(4-methoxy-benzyloxy)-amino]-propionic acid

Guidance literature:: Multi-step reaction with 9 steps

1.1: potassium carbonate

2.1: [Cp₂Zr(H)Cl] / CH₂Cl₂ / 20 °C

2.2: 77 percent / iodine / CH₂Cl₂

3.1: 74 percent / tetrakis(triphenylphosphine)palladium⁽⁰⁾ / tetrahydrofuran; diethyl ether; pentane / -30 - 20 °C

4.1: 90 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂

5.1: EtAlCl₂ / toluene / -78 - 22 °C

6.1: lithium hexamethyldisilazide / tetrahydrofuran / -78 - 0 °C

6.2: 62 percent / tetrahydrofuran; hexamethylphosphoric acid triamide

7.1: 81 percent / potassium hydroxide / methanol; H₂O / 0 °C

8.1: 99 percent / BOP; triethylamine / acetonitrile / 20 °C

9.1: 85 percent / pyrrolidine / tetrakis(triphenylphosphine)palladium⁽⁰⁾ / CH₂Cl₂

With pyrrolidine; pyridine; potassium hydroxide; Schwartz's reagent; ethylaluminum dichloride; potassium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; Dess-Martin periodane; triethylamine; lithium hexamethyldisilazane; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene; acetonitrile; pentane; 3.1: Negishi coupling / 5.1: Diels-Alder reaction;
DOI:10.1002/anie.200502015

Reference yield:

: (E)-(S)-7-Methyl-dec-3-en-9-yn-2-one

: 872472-48-5
(R)-2-[(1S,2R,5S,6R)-2,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-oxa-bicyclo[4.1.0]hept-2-yl]-3-[[3-((1S,2S,4aR,6S,8aS)-2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-3-oxo-propionyl]-(4-methoxy-benzyloxy)-amino]-propionic acid

Guidance literature:: Multi-step reaction with 8 steps

1.1: [Cp₂Zr(H)Cl] / CH₂Cl₂ / 20 °C

1.2: 77 percent / iodine / CH₂Cl₂

2.1: 74 percent / tetrakis(triphenylphosphine)palladium⁽⁰⁾ / tetrahydrofuran; diethyl ether; pentane / -30 - 20 °C

3.1: 90 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂

4.1: EtAlCl₂ / toluene / -78 - 22 °C

5.1: lithium hexamethyldisilazide / tetrahydrofuran / -78 - 0 °C

5.2: 62 percent / tetrahydrofuran; hexamethylphosphoric acid triamide

6.1: 81 percent / potassium hydroxide / methanol; H₂O / 0 °C

7.1: 99 percent / BOP; triethylamine / acetonitrile / 20 °C

8.1: 85 percent / pyrrolidine / tetrakis(triphenylphosphine)palladium⁽⁰⁾ / CH₂Cl₂

With pyrrolidine; pyridine; potassium hydroxide; Schwartz's reagent; ethylaluminum dichloride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; Dess-Martin periodane; triethylamine; lithium hexamethyldisilazane; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene; acetonitrile; pentane; 2.1: Negishi coupling / 4.1: Diels-Alder reaction;
DOI:10.1002/anie.200502015