1-O-Benzyl-2-O-[(3R,7R,11S,15S)-15-formyl-3,7,11,15-tetramethylpentadecanyl]-3-O-[(3R,7R,11R)-3,7,11,15-tetramethylhexadecanyl]-sn-glycerol

Base Information

Chemical Name:1-O-Benzyl-2-O-[(3R,7R,11S,15S)-15-formyl-3,7,11,15-tetramethylpentadecanyl]-3-O-[(3R,7R,11R)-3,7,11,15-tetramethylhexadecanyl]-sn-glycerol
CAS No.:307949-99-1
Molecular Formula:C₅₀H₉₂O₄
Molecular Weight:757.278
Hs Code.:

Synonyms:1-O-Benzyl-2-O-[(3R,7R,11S,15S)-15-formyl-3,7,11,15-tetramethylpentadecanyl]-3-O-[(3R,7R,11R)-3,7,11,15-tetramethylhexadecanyl]-sn-glycerol

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Chemical Property of 1-O-Benzyl-2-O-[(3R,7R,11S,15S)-15-formyl-3,7,11,15-tetramethylpentadecanyl]-3-O-[(3R,7R,11R)-3,7,11,15-tetramethylhexadecanyl]-sn-glycerol

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Technology Process of 1-O-Benzyl-2-O-[(3R,7R,11S,15S)-15-formyl-3,7,11,15-tetramethylpentadecanyl]-3-O-[(3R,7R,11R)-3,7,11,15-tetramethylhexadecanyl]-sn-glycerol

There total 5 articles about 1-O-Benzyl-2-O-[(3R,7R,11S,15S)-15-formyl-3,7,11,15-tetramethylpentadecanyl]-3-O-[(3R,7R,11R)-3,7,11,15-tetramethylhexadecanyl]-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: 80.0%

: 307949-98-0
1-O-Benzyl-2-O-[(3R,7R,11S,15S)-16-hydroxy-3,7,11,15-tetramethylhexadecanyl]-3-O-[(3R,7R,11R)-3,7,11,15-tetramethylhexadecanyl]-sn-glycerol

: 307949-99-1
1-O-Benzyl-2-O-[(3R,7R,11S,15S)-15-formyl-3,7,11,15-tetramethylpentadecanyl]-3-O-[(3R,7R,11R)-3,7,11,15-tetramethylhexadecanyl]-sn-glycerol

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - -25 ℃;
DOI:10.1002/1521-3765(20000915)6:18<3351::AID-CHEM3351>3.0.CO;2-4

Reference yield:

: 156593-00-9
Methanesulfonic acid (3R,7R,11S,15S)-16-(tert-butyl-dimethyl-silanyloxy)-3,7,11,15-tetramethyl-hexadecyl ester

: 307949-99-1
1-O-Benzyl-2-O-[(3R,7R,11S,15S)-15-formyl-3,7,11,15-tetramethylpentadecanyl]-3-O-[(3R,7R,11R)-3,7,11,15-tetramethylhexadecanyl]-sn-glycerol

Guidance literature:: Multi-step reaction with 3 steps

1.1: NaH / dimethylsulfoxide / 0.5 h / 20 °C

1.2: 61 percent / dimethylsulfoxide / 20 - 40 °C

2.1: 89 percent / TBAF / tetrahydrofuran / 8 h / 20 °C

3.1: 80 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - -25 °C

With oxalyl dichloride; tetrabutyl ammonium fluoride; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; 1.1: Metallation / 1.2: Etherification / 2.1: Substitution / 3.1: Oxidation;
DOI:10.1002/1521-3765(20000915)6:18<3351::AID-CHEM3351>3.0.CO;2-4

Reference yield:

: 4-Benzyloxymethyl-2-((2R,6R,10R)-2,6,10,14-tetramethyl-pentadecyl)-[1,3]dioxolane

: 307949-99-1
1-O-Benzyl-2-O-[(3R,7R,11S,15S)-15-formyl-3,7,11,15-tetramethylpentadecanyl]-3-O-[(3R,7R,11R)-3,7,11,15-tetramethylhexadecanyl]-sn-glycerol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 50 percent / DIBAL-H / toluene / 16.08 h / 0 - 20 °C

2.1: NaH / dimethylsulfoxide / 0.5 h / 20 °C

2.2: 61 percent / dimethylsulfoxide / 20 - 40 °C

3.1: 89 percent / TBAF / tetrahydrofuran / 8 h / 20 °C

4.1: 80 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - -25 °C

With oxalyl dichloride; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; toluene; 1.1: Ring cleavage / 2.1: Metallation / 2.2: Etherification / 3.1: Substitution / 4.1: Oxidation;
DOI:10.1002/1521-3765(20000915)6:18<3351::AID-CHEM3351>3.0.CO;2-4