prop-2-en-1-yl (5R,6R,7R,8R,11S,14S,17S)-14-[1-(benzyloxy)ethyl]-17-[(benzyloxy)methyl]-7-hydroxy-2,2,3,3,6,8-hexamethyl-9,12,15-trioxo-11-(propan-2-yl)-5-tridecyl-4-oxa-10,13,16-triaza-3-silaoctadecan-18-oate

Base Information

• Chemical Name: prop-2-en-1-yl (5R,6R,7R,8R,11S,14S,17S)-14-[1-(benzyloxy)ethyl]-17-[(benzyloxy)methyl]-7-hydroxy-2,2,3,3,6,8-hexamethyl-9,12,15-trioxo-11-(propan-2-yl)-5-tridecyl-4-oxa-10,13,16-triaza-3-silaoctadecan-18-oate
• CAS No.: 452956-88-6
• Molecular Formula: C₅₅H₉₁N₃O₉Si
• Molecular Weight: 966.428

Synonyms:prop-2-en-1-yl (5R,6R,7R,8R,11S,14S,17S)-14-[1-(benzyloxy)ethyl]-17-[(benzyloxy)methyl]-7-hydroxy-2,2,3,3,6,8-hexamethyl-9,12,15-trioxo-11-(propan-2-yl)-5-tridecyl-4-oxa-10,13,16-triaza-3-silaoctadecan-18-oate

Chemical Property of prop-2-en-1-yl (5R,6R,7R,8R,11S,14S,17S)-14-[1-(benzyloxy)ethyl]-17-[(benzyloxy)methyl]-7-hydroxy-2,2,3,3,6,8-hexamethyl-9,12,15-trioxo-11-(propan-2-yl)-5-tridecyl-4-oxa-10,13,16-triaza-3-silaoctadecan-18-oate

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Technology Process of prop-2-en-1-yl (5R,6R,7R,8R,11S,14S,17S)-14-[1-(benzyloxy)ethyl]-17-[(benzyloxy)methyl]-7-hydroxy-2,2,3,3,6,8-hexamethyl-9,12,15-trioxo-11-(propan-2-yl)-5-tridecyl-4-oxa-10,13,16-triaza-3-silaoctadecan-18-oate

There total 16 articles about prop-2-en-1-yl (5R,6R,7R,8R,11S,14S,17S)-14-[1-(benzyloxy)ethyl]-17-[(benzyloxy)methyl]-7-hydroxy-2,2,3,3,6,8-hexamethyl-9,12,15-trioxo-11-(propan-2-yl)-5-tridecyl-4-oxa-10,13,16-triaza-3-silaoctadecan-18-oate 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%

prop-2-en-1-yl (6S)-9-[ (1R)-1-(benzyloxy)ethyl]-12-[(benzyloxy)methyl]-2,2-dimethyl-4,7,10-trioxo-6-(propan-2-yl)-3-oxa-5,8,11-triazatridecan-13-oate (452956-86-4) + (2R,3R,4R,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-2,4-dimethyloctadecanoic acid (452956-83-1) → prop-2-en-1-yl (5R,6R,7R,8R,11S,14S,17S)-14-[1-(benzyloxy)ethyl]-17-[(benzyloxy)methyl]-7-hydroxy-2,2,3,3,6,8-hexamethyl-9,12,15-trioxo-11-(propan-2-yl)-5-tridecyl-4-oxa-10,13,16-triaza-3-silaoctadecan-18-oate (452956-88-6)

Guidance literature:

prop-2-en-1-yl (6S)-9-[ (1R)-1-(benzyloxy)ethyl]-12-[(benzyloxy)methyl]-2,2-dimethyl-4,7,10-trioxo-6-(propan-2-yl)-3-oxa-5,8,11-triazatridecan-13-oate; With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 3h; Inert atmosphere;

(2R,3R,4R,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-2,4-dimethyloctadecanoic acid; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20 ℃; for 4h; Inert atmosphere;

DOI:10.1002/hlca.201300255

Reference yield:

ethyl (2E,4R,5R)-5-{[(tert-butyl)(dimethyl)silyl]oxy}-2,4-dimethyloctadec-2-enoate (1613724-87-0) → prop-2-en-1-yl (5R,6R,7R,8R,11S,14S,17S)-14-[1-(benzyloxy)ethyl]-17-[(benzyloxy)methyl]-7-hydroxy-2,2,3,3,6,8-hexamethyl-9,12,15-trioxo-11-(propan-2-yl)-5-tridecyl-4-oxa-10,13,16-triaza-3-silaoctadecan-18-oate (452956-88-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -10 °C / Inert atmosphere

2.1: dimethylsulfide borane complex / tetrahydrofuran / 4.25 h / 0 - 20 °C / Inert atmosphere

3.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 2 h / 0 °C / Inert atmosphere

4.1: 2-methyl-but-2-ene; sodium dihydrogenphosphate dihydrate; sodium chlorite / water; acetonitrile / 0.33 h / 20 °C / Inert atmosphere

5.1: trifluoroacetic acid / dichloromethane / 3 h / 0 °C / Inert atmosphere

5.2: 4 h / 0 - 20 °C / Inert atmosphere

With sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; dimethylsulfide borane complex; diisobutylaluminium hydride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; toluene; acetonitrile;

DOI:10.1002/hlca.201300255

Reference yield:

1-Tetradecanol (112-72-1) → prop-2-en-1-yl (5R,6R,7R,8R,11S,14S,17S)-14-[1-(benzyloxy)ethyl]-17-[(benzyloxy)methyl]-7-hydroxy-2,2,3,3,6,8-hexamethyl-9,12,15-trioxo-11-(propan-2-yl)-5-tridecyl-4-oxa-10,13,16-triaza-3-silaoctadecan-18-oate (452956-88-6)

Guidance literature:

Multi-step reaction with 13 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C / Inert atmosphere

1.2: -78 - -50 °C / Inert atmosphere

2.1: benzene / Reflux; Inert atmosphere

3.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -10 °C / Inert atmosphere

4.1: titanium(IV) isopropylate; diethyl (2S,3S)-tartrate; tert.-butylhydroperoxide / dichloromethane; toluene / 2.83 h / -25 °C / Molecular sieve; Inert atmosphere

5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / -45 °C / Molecular sieve; Inert atmosphere

6.1: hydrogenchloride / water; tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere

7.1: benzene / 12 h / Reflux; Inert atmosphere

8.1: 2,6-dimethylpyridine / dichloromethane / 2 h / 20 °C / Inert atmosphere

9.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -10 °C / Inert atmosphere

10.1: dimethylsulfide borane complex / tetrahydrofuran / 4.25 h / 0 - 20 °C / Inert atmosphere

11.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 2 h / 0 °C / Inert atmosphere

12.1: 2-methyl-but-2-ene; sodium dihydrogenphosphate dihydrate; sodium chlorite / water; acetonitrile / 0.33 h / 20 °C / Inert atmosphere

13.1: trifluoroacetic acid / dichloromethane / 3 h / 0 °C / Inert atmosphere

13.2: 4 h / 0 - 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene; oxalyl dichloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; diethyl (2S,3S)-tartrate; [bis(acetoxy)iodo]benzene; dimethylsulfide borane complex; diisobutylaluminium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; toluene; acetonitrile; benzene; 1.1: |Swern Oxidation / 1.2: |Swern Oxidation / 2.1: |Wittig Olefination / 4.1: |Sharpless Asymmetric Epoxidation / 7.1: |Wittig Olefination;

DOI:10.1002/hlca.201300255

upstream raw materials:

1-Tetradecanol

ethyl (2E,4R,5R)-5-{[(tert-butyl)(dimethyl)silyl]oxy}-2,4-dimethyloctadec-2-enoate

(2E,4R,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-2,4-dimethyloctadec-2-en-1-ol

(2S,3S,4R,5R)-5-{[(tert-butyl)(dimethyl)silyl]oxy}-2,4-dimethyloctadecane-1,3-diol

Downstream raw materials:

(2S)-3-(benzyloxy)-2-{[(2S)-3-(benzyloxy)-2-{[(2S)-2-{[(2R,3R,4S,5R)-3,5-dihydroxy-2,4-dimethyloctadecanoyl]amino}-3-methylbutanoyl]amino}butanoyl]amino}propanoic acid

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