1-O-benzyl-2,3-di-O-phytyl-sn-glycerol

Base Information

• Chemical Name: 1-O-benzyl-2,3-di-O-phytyl-sn-glycerol
• CAS No.: 79974-51-9
• Molecular Formula: C₅₀H₉₀O₃
• Molecular Weight: 739.263
• Mol file: 79974-51-9.mol

Synonyms:

Chemical Property of 1-O-benzyl-2,3-di-O-phytyl-sn-glycerol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-O-benzyl-2,3-di-O-phytyl-sn-glycerol

There total 1 articles about 1-O-benzyl-2,3-di-O-phytyl-sn-glycerol 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:

(Z)-1-bromo-3,7,11,15-tetramethylhexadec-2-ene (4444-13-7,76524-59-9,76672-75-8) + (2S)-3-(benzyloxy)propane-1,2-diol (17325-85-8) → 1-O-benzyl-2,3-di-O-phytyl-sn-glycerol (79974-51-9,121521-37-7)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 20h;

DOI:10.1016/0008-6215(84)85200-3

Reference yield:

1-O-benzyl-2,3-di-O-phytyl-sn-glycerol (79974-51-9,121521-37-7) → 2-Formyl-benzoic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(S)-2,3-bis-(3,7,11,15-tetramethyl-hexadecyloxy)-propoxy]-tetrahydro-pyran-3-yl ester (95058-07-4)

Guidance literature:

Multi-step reaction with 8 steps

1: hydrogen / 10 percent Pd/C / acetic acid / 16 h / 2280 Torr

2: tetraethylammonium bromide, di-isopropylethylamine, molecular sieves 4 Angstroem / CH₂Cl₂; dimethylformamide / 96 h

3: 82 percent / hydrogen / 10 percent Pd/C / acetic acid / 24 h / 20 °C / 3040 Torr

4: 64 percent / pyridine / 3 h / -15 °C

5: 100 percent / pyridine / tetrahydrofuran / 1 h / 0 °C

6: 58 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 20 °C

7: pyridine / 18 h / Ambient temperature

8: silver triflate, 2,6-dimethylpyridine / acetone; H₂O / 2 h / 20 °C

With pyridine; 2,6-dimethylpyridine; 4 A molecular sieve; tetraethylammonium bromide; tetrabutyl ammonium fluoride; hydrogen; silver trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetone;

DOI:10.1016/0008-6215(84)85200-3

Reference yield:

1-O-benzyl-2,3-di-O-phytyl-sn-glycerol (79974-51-9,121521-37-7) → 2,3-O-phytanyl-1-O-<3,4,6-tri-O-acetyl-2-O-(2-dibromomethylbenzoyl)-α-D-glucopyranosyl>-sn-glycerol (79974-55-3,95188-85-5)

Guidance literature:

Multi-step reaction with 7 steps

1: hydrogen / 10 percent Pd/C / acetic acid / 16 h / 2280 Torr

2: tetraethylammonium bromide, di-isopropylethylamine, molecular sieves 4 Angstroem / CH₂Cl₂; dimethylformamide / 96 h

3: 82 percent / hydrogen / 10 percent Pd/C / acetic acid / 24 h / 20 °C / 3040 Torr

4: 64 percent / pyridine / 3 h / -15 °C

5: 100 percent / pyridine / tetrahydrofuran / 1 h / 0 °C

6: 58 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 20 °C

7: pyridine / 18 h / Ambient temperature

With pyridine; 4 A molecular sieve; tetraethylammonium bromide; tetrabutyl ammonium fluoride; hydrogen; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; acetic acid; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(84)85200-3

upstream raw materials:

(Z)-1-bromo-3,7,11,15-tetramethylhexadec-2-ene

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

Downstream raw materials:

2,3-di-O-phytanyl-sn-glycerol

1-O-(2-O-dibromomethylbenzoyl-α-D-glucopyranosyl)-2,3-di-O-phytanyl-sn-glycerol

2-Formyl-benzoic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(S)-2,3-bis-(3,7,11,15-tetramethyl-hexadecyloxy)-propoxy]-tetrahydro-pyran-3-yl ester

2,3-O-phytanyl-1-O-<3,4,6-tri-O-acetyl-2-O-(2-dibromomethylbenzoyl)-α-D-glucopyranosyl>-sn-glycerol

Refernces