Phenacyl (3R)-3-phenylmethoxytetradecanoate

Base Information

• Chemical Name: Phenacyl (3R)-3-phenylmethoxytetradecanoate
• CAS No.: 87357-66-2
• Molecular Formula: C29H40O4
• Molecular Weight: 452.634
• DSSTox Substance ID: DTXSID30447489
• Wikidata: Q82266369
• Mol file: 87357-66-2.mol

Synonyms:Phenacyl (3R)-3-phenylmethoxytetradecanoate;87357-66-2;SCHEMBL2309972;DTXSID30447489

Chemical Property of Phenacyl (3R)-3-phenylmethoxytetradecanoate

Chemical Property:

• XLogP3: 8.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 19
• Exact Mass: 452.29265975
• Heavy Atom Count: 33
• Complexity: 506

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCC(CC(=O)OCC(=O)C1=CC=CC=C1)OCC2=CC=CC=C2
• Isomeric SMILES: CCCCCCCCCCC[C@H](CC(=O)OCC(=O)C1=CC=CC=C1)OCC2=CC=CC=C2

Technology Process of Phenacyl (3R)-3-phenylmethoxytetradecanoate

There total 8 articles about Phenacyl (3R)-3-phenylmethoxytetradecanoate 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: 99.0%

(3R)-3-hydroxytetradecanoic acid phenacyl ester (87357-65-1) + benzaldehyde (100-52-7) → phrnacyl (R)-3-(benzyloxy)tetradecanoate (87357-66-2)

Guidance literature:

With triethylsilane; Hexamethyldisiloxane; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran;

DOI:10.1016/S0040-4020(98)00133-1

Reference yield: 74.0%

O-benzyl 2,2,2-trichloroacetimidate (81927-55-1) + (3R)-3-hydroxytetradecanoic acid phenacyl ester (87357-65-1) → phrnacyl (R)-3-(benzyloxy)tetradecanoate (87357-66-2)

Guidance literature:

With trifluorormethanesulfonic acid; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1246/bcsj.60.2197

Reference yield:

(R)-3-hydroxytetradecanoic acid (28715-21-1,3422-31-9) → phrnacyl (R)-3-(benzyloxy)tetradecanoate (87357-66-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 36.0 g / triethylamine / ethyl acetate

2: 99 percent / hexamethyldisiloxane; TMSOTf; triethylsilane / tetrahydrofuran

With triethylsilane; Hexamethyldisiloxane; trimethylsilyl trifluoromethanesulfonate; triethylamine; In tetrahydrofuran; ethyl acetate; 1: Esterification / 2: Alkylation;

DOI:10.1016/S0040-4020(98)00133-1

upstream raw materials:

O-benzyl 2,2,2-trichloroacetimidate

(3R)-3-hydroxytetradecanoic acid phenacyl ester

benzyl bromide

benzaldehyde

Downstream raw materials:

Benzoic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-[(2R,3R,4R,5S,6R)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-3-((R)-3-benzyloxy-tetradecanoylamino)-tetrahydro-pyran-2-yloxymethyl]-6-allyloxy-5-((R)-3-benzyloxy-tetradecanoylamino)-tetrahydro-pyran-4-yl ester

(R)-3-Benzyloxy-tetradecanoic acid {(2R,3R,4R,5S,6R)-2-[(2R,3S,4R,5R,6R)-6-allyloxy-5-((R)-3-benzyloxy-tetradecanoylamino)-3,4-dihydroxy-tetrahydro-pyran-2-ylmethoxy]-4-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-amide

(R)-3-Benzyloxy-tetradecanoic acid {(4aR,6R,7R,8R,8aS)-6-[(2R,3S,4R,5R,6R)-6-allyloxy-5-((R)-3-benzyloxy-tetradecanoylamino)-3,4-dihydroxy-tetrahydro-pyran-2-ylmethoxy]-8-benzyloxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-amide

(R)-3-Benzyloxy-tetradecanoic acid (2R,3S,4R,5R,6R)-5-acetylamino-2-((2R,3R,4R,5S,6R)-3-acetylamino-4-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-6-allyloxy-4-((R)-3-benzyloxy-tetradecanoyloxy)-tetrahydro-pyran-3-yl ester