(S)-(2S,3S,4R,5S,8R,9S,Z)-4-(tert-butyldimethylsilyloxy)-8-(methoxymethoxy)-3,5,7,9-tetramethylundeca-6,10-dien-2-yl 2-(tert-butoxycarbonyl(methyl)amino)-3-phenylpropanoate

Base Information

Chemical Name:(S)-(2S,3S,4R,5S,8R,9S,Z)-4-(tert-butyldimethylsilyloxy)-8-(methoxymethoxy)-3,5,7,9-tetramethylundeca-6,10-dien-2-yl 2-(tert-butoxycarbonyl(methyl)amino)-3-phenylpropanoate
CAS No.:1459205-37-8
Molecular Formula:C₃₈H₆₅NO₇Si
Molecular Weight:676.022
Hs Code.:

(S)-(2S,3S,4R,5S,8R,9S,Z)-4-(tert-butyldimethylsilyloxy)-8-(methoxymethoxy)-3,5,7,9-tetramethylundeca-6,10-dien-2-yl 2-(tert-butoxycarbonyl(methyl)amino)-3-phenylpropanoate

Synonyms:(S)-(2S,3S,4R,5S,8R,9S,Z)-4-(tert-butyldimethylsilyloxy)-8-(methoxymethoxy)-3,5,7,9-tetramethylundeca-6,10-dien-2-yl 2-(tert-butoxycarbonyl(methyl)amino)-3-phenylpropanoate

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Chemical Property of (S)-(2S,3S,4R,5S,8R,9S,Z)-4-(tert-butyldimethylsilyloxy)-8-(methoxymethoxy)-3,5,7,9-tetramethylundeca-6,10-dien-2-yl 2-(tert-butoxycarbonyl(methyl)amino)-3-phenylpropanoate

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Technology Process of (S)-(2S,3S,4R,5S,8R,9S,Z)-4-(tert-butyldimethylsilyloxy)-8-(methoxymethoxy)-3,5,7,9-tetramethylundeca-6,10-dien-2-yl 2-(tert-butoxycarbonyl(methyl)amino)-3-phenylpropanoate

There total 15 articles about (S)-(2S,3S,4R,5S,8R,9S,Z)-4-(tert-butyldimethylsilyloxy)-8-(methoxymethoxy)-3,5,7,9-tetramethylundeca-6,10-dien-2-yl 2-(tert-butoxycarbonyl(methyl)amino)-3-phenylpropanoate 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: 88.0%

: 37553-65-4
Boc-N-Me-Phe-OH

: 1459205-35-6
(2S,3S,4R,5S,8R,9S,Z)-4-(tert-butyldimethylsilyloxy)-8-(methoxymethoxy)-3,5,7,9-tetramethylundeca-6,10-dien-2-ol

: 1459205-37-8
(S)-(2S,3S,4R,5S,8R,9S,Z)-4-(tert-butyldimethylsilyloxy)-8-(methoxymethoxy)-3,5,7,9-tetramethylundeca-6,10-dien-2-yl 2-(tert-butoxycarbonyl(methyl)amino)-3-phenylpropanoate

Guidance literature:: Boc-N-Me-Phe-OH; With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 ℃; for 0.166667h;

(2S,3S,4R,5S,8R,9S,Z)-4-(tert-butyldimethylsilyloxy)-8-(methoxymethoxy)-3,5,7,9-tetramethylundeca-6,10-dien-2-ol; In dichloromethane; at 0 - 20 ℃; for 3h;
DOI:10.1039/c3ra42127a

Reference yield:

: 1459205-22-1
(2S,3S,4R,5S)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexane-2,4-diol

: 1459205-37-8
(S)-(2S,3S,4R,5S,8R,9S,Z)-4-(tert-butyldimethylsilyloxy)-8-(methoxymethoxy)-3,5,7,9-tetramethylundeca-6,10-dien-2-yl 2-(tert-butoxycarbonyl(methyl)amino)-3-phenylpropanoate

Guidance literature:: Multi-step reaction with 14 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.33 h / 0 °C / Inert atmosphere

1.2: 6 h / 0 °C / Inert atmosphere

2.1: 2,6-dimethylpyridine / dichloromethane / 0.08 h / -78 °C / Inert atmosphere

2.2: 1 h / -78 - -20 °C / Inert atmosphere

3.1: ammonium fluoride; methanol / 48 h / 20 °C

4.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; dimethyl sulfoxide / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

5.1: potassium carbonate; 18-crown-6 ether / toluene / 3 h / 0 °C / Inert atmosphere

6.1: diisobutylaluminium hydride / dichloromethane / 1.5 h / -78 - 0 °C / Inert atmosphere

7.1: manganese(IV) oxide / dichloromethane / 28 h / 20 °C / Inert atmosphere

8.1: titanium tetrachloride / dichloromethane / 0.25 h / 0 °C

8.2: 0.5 h / 0 °C

8.3: 2 h / -78 °C

9.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.25 h / 0 °C

9.2: 12 h / 0 - 20 °C / Inert atmosphere

10.1: lithium borohydride / diethyl ether; methanol / 2 h / 0 - 20 °C

11.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; dimethyl sulfoxide / tetrahydrofuran / 0.75 h / 20 °C / Inert atmosphere

12.1: potassium tert-butylate / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

12.2: 0.25 h / 0 °C / Inert atmosphere

13.1: lithium; naphthalene / tetrahydrofuran / 0.25 h / -20 °C

14.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 0.17 h / 0 °C

14.2: 3 h / 0 - 20 °C

With 2,6-dimethylpyridine; methanol; dmap; manganese(IV) oxide; ammonium fluoride; lithium borohydride; naphthalene; 18-crown-6 ether; potassium tert-butylate; titanium tetrachloride; lithium; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; mineral oil; 5.1: |Horner-Wadsworth-Emmons Olefination / 8.3: |Aldol Addition / 12.2: |Wittig Olefination;
DOI:10.1039/c3ra42127a

Reference yield:

: 1459205-23-2
(2S,3R,4R,5S)-5-benzyloxy-1-(tert-butyldiphenylsilyloxy)-2,4-dimethylhexan-3-ol

: 1459205-37-8
(S)-(2S,3S,4R,5S,8R,9S,Z)-4-(tert-butyldimethylsilyloxy)-8-(methoxymethoxy)-3,5,7,9-tetramethylundeca-6,10-dien-2-yl 2-(tert-butoxycarbonyl(methyl)amino)-3-phenylpropanoate

Guidance literature:: Multi-step reaction with 13 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 0.08 h / -78 °C / Inert atmosphere

1.2: 1 h / -78 - -20 °C / Inert atmosphere

2.1: ammonium fluoride; methanol / 48 h / 20 °C

3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; dimethyl sulfoxide / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

4.1: potassium carbonate; 18-crown-6 ether / toluene / 3 h / 0 °C / Inert atmosphere

5.1: diisobutylaluminium hydride / dichloromethane / 1.5 h / -78 - 0 °C / Inert atmosphere

6.1: manganese(IV) oxide / dichloromethane / 28 h / 20 °C / Inert atmosphere

7.1: titanium tetrachloride / dichloromethane / 0.25 h / 0 °C

7.2: 0.5 h / 0 °C

7.3: 2 h / -78 °C

8.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.25 h / 0 °C

8.2: 12 h / 0 - 20 °C / Inert atmosphere

9.1: lithium borohydride / diethyl ether; methanol / 2 h / 0 - 20 °C

10.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; dimethyl sulfoxide / tetrahydrofuran / 0.75 h / 20 °C / Inert atmosphere

11.1: potassium tert-butylate / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

11.2: 0.25 h / 0 °C / Inert atmosphere

12.1: lithium; naphthalene / tetrahydrofuran / 0.25 h / -20 °C

13.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 0.17 h / 0 °C

13.2: 3 h / 0 - 20 °C

With 2,6-dimethylpyridine; methanol; dmap; manganese(IV) oxide; ammonium fluoride; lithium borohydride; naphthalene; 18-crown-6 ether; potassium tert-butylate; titanium tetrachloride; lithium; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; 4.1: |Horner-Wadsworth-Emmons Olefination / 7.3: |Aldol Addition / 11.2: |Wittig Olefination;
DOI:10.1039/c3ra42127a