Hexadecanoic acid (R)-2-benzyloxy-3-[(2-chloro-ethoxy)-hydroxy-phosphoryloxy]-propyl ester

Base Information

• Chemical Name: Hexadecanoic acid (R)-2-benzyloxy-3-[(2-chloro-ethoxy)-hydroxy-phosphoryloxy]-propyl ester
• CAS No.: 172794-56-8
• Molecular Formula: C₂₈H₄₈ClO₇P
• Molecular Weight: 563.112
• Mol file: 172794-56-8.mol

Synonyms:Hexadecanoic acid (R)-2-benzyloxy-3-[(2-chloro-ethoxy)-hydroxy-phosphoryloxy]-propyl ester

Chemical Property of Hexadecanoic acid (R)-2-benzyloxy-3-[(2-chloro-ethoxy)-hydroxy-phosphoryloxy]-propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Hexadecanoic acid (R)-2-benzyloxy-3-[(2-chloro-ethoxy)-hydroxy-phosphoryloxy]-propyl ester

There total 7 articles about Hexadecanoic acid (R)-2-benzyloxy-3-[(2-chloro-ethoxy)-hydroxy-phosphoryloxy]-propyl ester 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:

2-O-Benzyl-3-O-palmitoyl-D-glycerinaldehyd (17618-07-4) → Hexadecanoic acid (R)-2-benzyloxy-3-[(2-chloro-ethoxy)-hydroxy-phosphoryloxy]-propyl ester (172794-56-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / NaBH₄ / methanol / 4 h / Ambient temperature

2: 1.) Et₃N, 2.) H₂O / 1.) CH₂Cl₂, 0-5 deg C, 4 h, 2.) RT, 30 min

With sodium tetrahydroborate; water; triethylamine; In methanol;

DOI:10.1016/S0957-4166(97)00005-0

Reference yield:

1-hexadecylcarboxylic acid (57-10-3) → Hexadecanoic acid (R)-2-benzyloxy-3-[(2-chloro-ethoxy)-hydroxy-phosphoryloxy]-propyl ester (172794-56-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 84.6 percent / DMAP, DCC / CH₂Cl₂ / Ambient temperature

2: 70 percent / TFA, 70percent aq. HClo₄ / CH₂Cl₂ / 0.17 h / 0 - 5 °C

3: Pb(OAc)4 / ethyl acetate / 4 h / Ambient temperature

4: 83 percent / NaBH₄ / methanol / 4 h / Ambient temperature

5: 1.) Et₃N, 2.) H₂O / 1.) CH₂Cl₂, 0-5 deg C, 4 h, 2.) RT, 30 min

With lead(IV) acetate; dmap; sodium tetrahydroborate; perchloric acid; water; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In methanol; dichloromethane; ethyl acetate;

DOI:10.1016/S0957-4166(97)00005-0

Reference yield:

2,5,6-tribenzyl-3,4-isopropylidene-D-mannitol → Hexadecanoic acid (R)-2-benzyloxy-3-[(2-chloro-ethoxy)-hydroxy-phosphoryloxy]-propyl ester (172794-56-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 84.6 percent / DMAP, DCC / CH₂Cl₂ / Ambient temperature

2: 70 percent / TFA, 70percent aq. HClo₄ / CH₂Cl₂ / 0.17 h / 0 - 5 °C

3: Pb(OAc)4 / ethyl acetate / 4 h / Ambient temperature

4: 83 percent / NaBH₄ / methanol / 4 h / Ambient temperature

5: 1.) Et₃N, 2.) H₂O / 1.) CH₂Cl₂, 0-5 deg C, 4 h, 2.) RT, 30 min

With lead(IV) acetate; dmap; sodium tetrahydroborate; perchloric acid; water; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In methanol; dichloromethane; ethyl acetate;

DOI:10.1016/S0957-4166(97)00005-0

upstream raw materials:

2-chloroethyl phosphorodichloridate

(S)-3-O-palmitoyl-2-O-benzylglycerol

2-O-Benzyl-3-O-palmitoyl-D-glycerinaldehyd

1-hexadecylcarboxylic acid

Downstream raw materials:

1-palmitoyl-2-benzylglycerophosphocholine

1-palmitoyl-sn-glycero-3-phosphocholine