(2S,6S,10R,14R)-16-[(S)-2-Benzyloxy-1-((3R,7R,11S,15S)-3,7,11,15-tetramethyl-16-oxo-hexadecyloxymethyl)-ethoxy]-2,6,10,14-tetramethyl-hexadecanal

Base Information

• Chemical Name: (2S,6S,10R,14R)-16-[(S)-2-Benzyloxy-1-((3R,7R,11S,15S)-3,7,11,15-tetramethyl-16-oxo-hexadecyloxymethyl)-ethoxy]-2,6,10,14-tetramethyl-hexadecanal
• CAS No.: 156593-03-2
• Molecular Formula: C₅₀H₉₀O₅
• Molecular Weight: 771.262
• Mol file: 156593-03-2.mol

Synonyms:(2S,6S,10R,14R)-16-[(S)-2-Benzyloxy-1-((3R,7R,11S,15S)-3,7,11,15-tetramethyl-16-oxo-hexadecyloxymethyl)-ethoxy]-2,6,10,14-tetramethyl-hexadecanal

Chemical Property of (2S,6S,10R,14R)-16-[(S)-2-Benzyloxy-1-((3R,7R,11S,15S)-3,7,11,15-tetramethyl-16-oxo-hexadecyloxymethyl)-ethoxy]-2,6,10,14-tetramethyl-hexadecanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,6S,10R,14R)-16-[(S)-2-Benzyloxy-1-((3R,7R,11S,15S)-3,7,11,15-tetramethyl-16-oxo-hexadecyloxymethyl)-ethoxy]-2,6,10,14-tetramethyl-hexadecanal

There total 30 articles about (2S,6S,10R,14R)-16-[(S)-2-Benzyloxy-1-((3R,7R,11S,15S)-3,7,11,15-tetramethyl-16-oxo-hexadecyloxymethyl)-ethoxy]-2,6,10,14-tetramethyl-hexadecanal 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: 76.0%

1-O-benzyl-2,3-bis-O-<(3R,7R,11S,15S)-16-hydroxy-3,7,11,15-tetramethylhexadecanyl>-sn-glycerol (156593-02-1) → (2S,6S,10R,14R)-16-[(S)-2-Benzyloxy-1-((3R,7R,11S,15S)-3,7,11,15-tetramethyl-16-oxo-hexadecyloxymethyl)-ethoxy]-2,6,10,14-tetramethyl-hexadecanal (156593-03-2)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1039/c3ob27277j

Reference yield:

(S)-4-Hydroxy-3-methyl-butyric acid (77220-86-1,108772-87-8) → (2S,6S,10R,14R)-16-[(S)-2-Benzyloxy-1-((3R,7R,11S,15S)-3,7,11,15-tetramethyl-16-oxo-hexadecyloxymethyl)-ethoxy]-2,6,10,14-tetramethyl-hexadecanal (156593-03-2)

Guidance literature:

Multi-step reaction with 17 steps

1: imidazole / dimethylformamide

2: DIBAH

3: TfOH / diethyl ether

4: aq. HCl / tetrahydrofuran

5: pyridine

6: K₂CO₃ / dimethylformamide

7: m-CPBA / CH₂Cl₂

8: 1.) BuLi, HMPA / 1.) THF, -78 deg C, 2.) THF, from -25 deg C to RT

9: 86 percent / Na(Hg) / methanol

10: H₂ / 10percent Pd/C / ethyl acetate

11: I₂, Ph₃P, imidazole / benzene

12: 1.) BuLi, HMPA / 1.) THF, -78 deg C, 2.) THF, from -25 deg C to RT

13: Li, EtNH₂ / tetrahydrofuran / -78 °C

14: Et₃N / CH₂Cl₂

15: 1.) NaH / 1.) DMSO, 2.) DMSO

16: aq. HCl / tetrahydrofuran

17: PCC, AcONa, molecular sieves 4A / CH₂Cl₂

With pyridine; 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; sodium amalgam; trifluorormethanesulfonic acid; 4 A molecular sieve; hydrogen; iodine; sodium acetate; lithium; sodium hydride; diisobutylaluminium hydride; potassium carbonate; ethylamine; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; benzene;

DOI:10.1039/c39940000137

Reference yield:

(3S)-4-<(1-ethoxyethyl)oxy>-3-methylbutanenitrile (188692-77-5) → (2S,6S,10R,14R)-16-[(S)-2-Benzyloxy-1-((3R,7R,11S,15S)-3,7,11,15-tetramethyl-16-oxo-hexadecyloxymethyl)-ethoxy]-2,6,10,14-tetramethyl-hexadecanal (156593-03-2)

Guidance literature:

Multi-step reaction with 18 steps

1: aq. HCl / tetrahydrofuran

2: imidazole / dimethylformamide

3: DIBAH

4: TfOH / diethyl ether

5: aq. HCl / tetrahydrofuran

6: pyridine

7: K₂CO₃ / dimethylformamide

8: m-CPBA / CH₂Cl₂

9: 1.) BuLi, HMPA / 1.) THF, -78 deg C, 2.) THF, from -25 deg C to RT

10: 86 percent / Na(Hg) / methanol

11: H₂ / 10percent Pd/C / ethyl acetate

12: I₂, Ph₃P, imidazole / benzene

13: 1.) BuLi, HMPA / 1.) THF, -78 deg C, 2.) THF, from -25 deg C to RT

14: Li, EtNH₂ / tetrahydrofuran / -78 °C

15: Et₃N / CH₂Cl₂

16: 1.) NaH / 1.) DMSO, 2.) DMSO

17: aq. HCl / tetrahydrofuran

18: PCC, AcONa, molecular sieves 4A / CH₂Cl₂

With pyridine; 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; sodium amalgam; trifluorormethanesulfonic acid; 4 A molecular sieve; hydrogen; iodine; sodium acetate; lithium; sodium hydride; diisobutylaluminium hydride; potassium carbonate; ethylamine; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; benzene;

DOI:10.1039/c39940000137

upstream raw materials:

1-O-benzyl-2,3-bis-O-<(3R,7R,11S,15S)-16-hydroxy-3,7,11,15-tetramethylhexadecanyl>-sn-glycerol

(2S)-3-(benzyloxy)propane-1,2-diol

(3R,7S)-8-<(tert-butyldimethylsilyl)oxy>-3,7-dimethyl-1-iodooctane

(3R,7R,11S,15S)-16-(tert-Butyl-dimethyl-silanyloxy)-3,7,11,15-tetramethyl-hexadecan-1-ol

Downstream raw materials:

C₅₀H₉₂O₃

[(S)-2,3-Bis-((3R,7R,11S,15S)-3,7,11,15-tetramethyl-heptadec-16-enyloxy)-propoxymethyl]-benzene

(E)-(2S,7R,11R,15S,19S,22S,26S,30R,34R)-2-Benzyloxymethyl-7,11,15,19,22,26,30,34-octamethyl-1,4-dioxa-cyclohexatriacont-20-ene

Refernces

• 1、 Eguchi, Tadashi,Arakawa, Kenji,Terachi, Takumi,Kakinuma, Katsumi. "Total synthesis of archaeal 36-membered macrocyclic diether lipid". . p. 1924 - 1933. Retrieved 2007/10/03.