(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

Base Information

• Chemical Name: (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
• CAS No.: 1613724-79-0
• Molecular Formula: C₃₈H₆₅NO₇
• Molecular Weight: 647.937

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (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

There total 10 articles about (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 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:

1-Tetradecanol (112-72-1) → (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)

Guidance literature:

Multi-step reaction with 11 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: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -10 °C / Inert atmosphere

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

10.1: (1S)-10-camphorsulfonic acid / dichloromethane / 0.08 h / 20 °C / Inert atmosphere

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

11.2: 2.5 h / 0 °C / Inert atmosphere

With titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; dmap; oxalyl dichloride; diethyl (2S,3S)-tartrate; dimethylsulfide borane complex; (1S)-10-camphorsulfonic acid; diisobutylaluminium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; water; toluene; 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

Reference yield:

ethyl (2E)-2-methylhexadec-2-enoate (478690-77-6) → (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)

Guidance literature:

Multi-step reaction with 9 steps

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

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

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

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

5.1: benzene / 12 h / Reflux; Inert atmosphere

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

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

8.1: (1S)-10-camphorsulfonic acid / dichloromethane / 0.08 h / 20 °C / Inert atmosphere

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

9.2: 2.5 h / 0 °C / Inert atmosphere

With titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; dmap; diethyl (2S,3S)-tartrate; dimethylsulfide borane complex; (1S)-10-camphorsulfonic acid; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; water; toluene; benzene; 2.1: |Sharpless Asymmetric Epoxidation / 5.1: |Wittig Olefination;

DOI:10.1002/hlca.201300255

Reference yield:

(E)-2-Methyl-hexadec-2-en-1-ol → (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)

Guidance literature:

Multi-step reaction with 8 steps

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

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

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

4.1: benzene / 12 h / Reflux; Inert atmosphere

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

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

7.1: (1S)-10-camphorsulfonic acid / dichloromethane / 0.08 h / 20 °C / Inert atmosphere

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

8.2: 2.5 h / 0 °C / Inert atmosphere

With titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; dmap; diethyl (2S,3S)-tartrate; dimethylsulfide borane complex; (1S)-10-camphorsulfonic acid; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; water; toluene; benzene; 1.1: |Sharpless Asymmetric Epoxidation / 4.1: |Wittig Olefination;

DOI:10.1002/hlca.201300255

upstream raw materials:

1-Tetradecanol

ethyl (2E)-2-methylhexadec-2-enoate

[(3R)-2-methyl-3-tridecyloxiran-2-yl]methanol

myristylaldehyde

Downstream raw materials:

(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

prop-2-en-1-yl (6S,12R)-18-[(1S)-1-(benzyloxy)ethyl]-6-[ (benzyloxy)methyl]-11-hydroxy-2,2,10,12-tetramethyl-4,7,13,16-tetraoxo-15-(propan-2-yl)-9-tridecyl-3,8-dioxa-5,14,17-triazanonadecan-19-oate

(6S,12R)-18-[(1S)-1-(benzyloxy)ethyl]-6-[(benzyloxy)methyl]-11-hydroxy-2,2,10,12-tetramethyl-4,7,13,16-tetraoxo-15-(propan-2-yl)-9-tridecyl-3,8-dioxa-5,14,17-triazanonadecan-19-oic acid

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