(3S,6S,9S)-6-[1-(benzyloxy)ethyl]-3-[(benzyloxy)methyl]-13-hydroxy-12,14-dimethyl-9-(propan-2-yl)-15-tridecyl-1-oxa-4,7,10-triazacyclopentadecane-2,5,8,11-tetrone

Base Information

• Chemical Name: (3S,6S,9S)-6-[1-(benzyloxy)ethyl]-3-[(benzyloxy)methyl]-13-hydroxy-12,14-dimethyl-9-(propan-2-yl)-15-tridecyl-1-oxa-4,7,10-triazacyclopentadecane-2,5,8,11-tetrone
• CAS No.: 1613724-85-8
• Molecular Formula: C₄₆H₇₁N₃O₈
• Molecular Weight: 794.085

Synonyms:

Chemical Property of (3S,6S,9S)-6-[1-(benzyloxy)ethyl]-3-[(benzyloxy)methyl]-13-hydroxy-12,14-dimethyl-9-(propan-2-yl)-15-tridecyl-1-oxa-4,7,10-triazacyclopentadecane-2,5,8,11-tetrone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,6S,9S)-6-[1-(benzyloxy)ethyl]-3-[(benzyloxy)methyl]-13-hydroxy-12,14-dimethyl-9-(propan-2-yl)-15-tridecyl-1-oxa-4,7,10-triazacyclopentadecane-2,5,8,11-tetrone

There total 21 articles about (3S,6S,9S)-6-[1-(benzyloxy)ethyl]-3-[(benzyloxy)methyl]-13-hydroxy-12,14-dimethyl-9-(propan-2-yl)-15-tridecyl-1-oxa-4,7,10-triazacyclopentadecane-2,5,8,11-tetrone 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:

(αR,βS,4S,5S)-β,2,2,5-tetramethyl-α-tridecyl-1,3-dioxan-4-ethanol → (3S,6S,9S)-6-[1-(benzyloxy)ethyl]-3-[(benzyloxy)methyl]-13-hydroxy-12,14-dimethyl-9-(propan-2-yl)-15-tridecyl-1-oxa-4,7,10-triazacyclopentadecane-2,5,8,11-tetrone (1613724-85-8)

Guidance literature:

Multi-step reaction with 8 steps

1.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

1.2: 2.5 h / 0 °C / Inert atmosphere

2.1: acetic acid / water / 10 h / 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 / 1 h / 0 °C / Inert atmosphere

5.2: 4.15 h / 0 - 20 °C / Inert atmosphere

6.1: morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 0.5 h / 25 °C / Inert atmosphere

7.1: trifluoroacetic acid / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

8.1: diisobutylaluminium hydride; diethyl cyanophosphonate / N,N-dimethyl-formamide / 48.5 h / 25 °C / Inert atmosphere

With morpholine; dmap; sodium chlorite; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; diethyl cyanophosphonate; [bis(acetoxy)iodo]benzene; diisobutylaluminium hydride; acetic acid; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/hlca.201300255

Reference yield:

(2S,3S,4R,5R)-1,3-dihydroxy-2,4-dimethyloctadecan-5-yl (2S)-3-(benzyloxy)-2-{[(tert-butoxy)carbonyl]amino}propanoate (1613724-80-3) → (3S,6S,9S)-6-[1-(benzyloxy)ethyl]-3-[(benzyloxy)methyl]-13-hydroxy-12,14-dimethyl-9-(propan-2-yl)-15-tridecyl-1-oxa-4,7,10-triazacyclopentadecane-2,5,8,11-tetrone (1613724-85-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 2 h / 0 °C / Inert atmosphere

2.1: 2-methyl-but-2-ene; sodium dihydrogenphosphate dihydrate; sodium chlorite / water; acetonitrile / 0.33 h / 20 °C / Inert atmosphere

3.1: trifluoroacetic acid / dichloromethane / 1 h / 0 °C / Inert atmosphere

3.2: 4.15 h / 0 - 20 °C / Inert atmosphere

4.1: morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 0.5 h / 25 °C / Inert atmosphere

5.1: trifluoroacetic acid / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

6.1: diisobutylaluminium hydride; diethyl cyanophosphonate / N,N-dimethyl-formamide / 48.5 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; diethyl cyanophosphonate; [bis(acetoxy)iodo]benzene; diisobutylaluminium hydride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/hlca.201300255

Reference yield:

(2S,3R)-2-[(4S,5S)-2,2,5-trimethyl-1,3-dioxan-4-yl]hexadecan-3-yl (2S)-3-(benzyloxy)-2-{[(tert-butoxy)carbonyl]amino}propanoate (1613724-79-0) → (3S,6S,9S)-6-[1-(benzyloxy)ethyl]-3-[(benzyloxy)methyl]-13-hydroxy-12,14-dimethyl-9-(propan-2-yl)-15-tridecyl-1-oxa-4,7,10-triazacyclopentadecane-2,5,8,11-tetrone (1613724-85-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: acetic acid / water / 10 h / 20 °C / Inert atmosphere

2.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 2 h / 0 °C / Inert atmosphere

3.1: 2-methyl-but-2-ene; sodium dihydrogenphosphate dihydrate; sodium chlorite / water; acetonitrile / 0.33 h / 20 °C / Inert atmosphere

4.1: trifluoroacetic acid / dichloromethane / 1 h / 0 °C / Inert atmosphere

4.2: 4.15 h / 0 - 20 °C / Inert atmosphere

5.1: morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 0.5 h / 25 °C / Inert atmosphere

6.1: trifluoroacetic acid / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

7.1: diisobutylaluminium hydride; diethyl cyanophosphonate / N,N-dimethyl-formamide / 48.5 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; diethyl cyanophosphonate; [bis(acetoxy)iodo]benzene; diisobutylaluminium hydride; acetic acid; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/hlca.201300255

upstream raw materials:

BOC-O-benzyl-L-serine

(2S,3R)-2-[(4S,5S)-2,2,5-trimethyl-1,3-dioxan-4-yl]hexadecan-3-yl (2S)-3-(benzyloxy)-2-{[(tert-butoxy)carbonyl]amino}propanoate

(2S,3S,4R,5R)-1,3-dihydroxy-2,4-dimethyloctadecan-5-yl (2S)-3-(benzyloxy)-2-{[(tert-butoxy)carbonyl]amino}propanoate

(2R,3R,4R,5R)-5-[ ((2S)-3-(benzyloxy)-2-{[(tert-butoxy)carbonyl]amino}propanoyl)oxy]-3-hydroxy-2,4-dimethyloctadecanoic acid

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