(5R,6R,7R,8R,11S,14S,17S)-14-[1-(benzyloxy)ethyl]-17-[(benzyloxy)methyl]-7-hydroxy-6,8-dimethyl-9,12,15-trioxo-11-(propan-2-yl)-5-tridecyl-2,4-dioxa-10,13,16-triazaoctadecan-18-oic acid

Base Information

• Chemical Name: (5R,6R,7R,8R,11S,14S,17S)-14-[1-(benzyloxy)ethyl]-17-[(benzyloxy)methyl]-7-hydroxy-6,8-dimethyl-9,12,15-trioxo-11-(propan-2-yl)-5-tridecyl-2,4-dioxa-10,13,16-triazaoctadecan-18-oic acid
• CAS No.: 1613724-69-8
• Molecular Formula: C₄₈H₇₇N₃O₁₀
• Molecular Weight: 856.153

Synonyms:(5R,6R,7R,8R,11S,14S,17S)-14-[1-(benzyloxy)ethyl]-17-[(benzyloxy)methyl]-7-hydroxy-6,8-dimethyl-9,12,15-trioxo-11-(propan-2-yl)-5-tridecyl-2,4-dioxa-10,13,16-triazaoctadecan-18-oic acid

Chemical Property of (5R,6R,7R,8R,11S,14S,17S)-14-[1-(benzyloxy)ethyl]-17-[(benzyloxy)methyl]-7-hydroxy-6,8-dimethyl-9,12,15-trioxo-11-(propan-2-yl)-5-tridecyl-2,4-dioxa-10,13,16-triazaoctadecan-18-oic acid

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (5R,6R,7R,8R,11S,14S,17S)-14-[1-(benzyloxy)ethyl]-17-[(benzyloxy)methyl]-7-hydroxy-6,8-dimethyl-9,12,15-trioxo-11-(propan-2-yl)-5-tridecyl-2,4-dioxa-10,13,16-triazaoctadecan-18-oic acid

There total 18 articles about (5R,6R,7R,8R,11S,14S,17S)-14-[1-(benzyloxy)ethyl]-17-[(benzyloxy)methyl]-7-hydroxy-6,8-dimethyl-9,12,15-trioxo-11-(propan-2-yl)-5-tridecyl-2,4-dioxa-10,13,16-triazaoctadecan-18-oic 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: 74.0%

prop-2-en-1-yl (5R,6R,7R,8R,11S,14S,17S)-14-[1-(benzyloxy)ethyl]-17-[(benzyloxy)methyl]-7-hydroxy-6,8-dimethyl-9,12,15-trioxo-11-(propan-2-yl)-5-tridecyl-2,4-dioxa-10,13,16-triazaoctadecan-18-oate (1613724-71-2) → (5R,6R,7R,8R,11S,14S,17S)-14-[1-(benzyloxy)ethyl]-17-[(benzyloxy)methyl]-7-hydroxy-6,8-dimethyl-9,12,15-trioxo-11-(propan-2-yl)-5-tridecyl-2,4-dioxa-10,13,16-triazaoctadecan-18-oic acid (1613724-69-8)

Guidance literature:

With morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 25 ℃; for 3h; Inert atmosphere;

DOI:10.1002/hlca.201300255

Reference yield:

ethyl (2E,4R,5R)-5-(methoxymethoxy)-2,4-dimethyloctadec-2-enoate (1613724-86-9) → (5R,6R,7R,8R,11S,14S,17S)-14-[1-(benzyloxy)ethyl]-17-[(benzyloxy)methyl]-7-hydroxy-6,8-dimethyl-9,12,15-trioxo-11-(propan-2-yl)-5-tridecyl-2,4-dioxa-10,13,16-triazaoctadecan-18-oic acid (1613724-69-8)

Guidance literature:

Multi-step reaction with 6 steps

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

2.1: dimethylsulfide borane complex / tetrahydrofuran / 4.25 h / -10 - 0 °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 / 1 h / 0 °C / Inert atmosphere

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

6.1: morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 3 h / 25 °C / Inert atmosphere

With morpholine; sodium chlorite; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 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) → (5R,6R,7R,8R,11S,14S,17S)-14-[1-(benzyloxy)ethyl]-17-[(benzyloxy)methyl]-7-hydroxy-6,8-dimethyl-9,12,15-trioxo-11-(propan-2-yl)-5-tridecyl-2,4-dioxa-10,13,16-triazaoctadecan-18-oic acid (1613724-69-8)

Guidance literature:

Multi-step reaction with 14 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: N-ethyl-N,N-diisopropylamine; dmap / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

8.2: 12 h / Inert atmosphere

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

10.1: dimethylsulfide borane complex / tetrahydrofuran / 4.25 h / -10 - 0 °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 / 1 h / 0 °C / Inert atmosphere

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

14.1: morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 3 h / 25 °C / Inert atmosphere

With morpholine; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; dmap; sodium chlorite; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 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:

ethyl (2E,4R,5R)-5-(methoxymethoxy)-2,4-dimethyloctadec-2-enoate

1-Tetradecanol

(2E,4R,5R)-5-(methoxymethoxy)-2,4-dimethyloctadec-2-en-1-ol

(2S,3S,4R,5R)-5-(methoxymethoxy)-2,4-dimethyloctadecane-1,3-diol

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