(2S,3S,4R)-1-(Trityloxy)-2-azidooctadecane-3,4-diol

Base Information

• Chemical Name: (2S,3S,4R)-1-(Trityloxy)-2-azidooctadecane-3,4-diol
• CAS No.: 160280-66-0
• Molecular Formula: C37H51N3O3
• Molecular Weight: 585.83
• DSSTox Substance ID: DTXSID801191733
• Nikkaji Number: J2.397.153D
• Mol file: 160280-66-0.mol

Synonyms:SCHEMBL19391304;DTXSID801191733;(2S,3S,4R)-1-(Trityloxy)-2-azidooctadecane-3,4-diol;(2S,3S,4R)-2-Azido-1-(triphenylmethoxy)-3,4-octadecanediol;160280-66-0

Chemical Property of (2S,3S,4R)-1-(Trityloxy)-2-azidooctadecane-3,4-diol

Chemical Property:

• XLogP3: 11.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 22
• Exact Mass: 585.39304250
• Heavy Atom Count: 43
• Complexity: 694

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCC(C(C(COC(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)N=[N+]=[N-])O)O
• Isomeric SMILES: CCCCCCCCCCCCCC[C@H]([C@H]([C@H](COC(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)N=[N+]=[N-])O)O

Technology Process of (2S,3S,4R)-1-(Trityloxy)-2-azidooctadecane-3,4-diol

There total 11 articles about (2S,3S,4R)-1-(Trityloxy)-2-azidooctadecane-3,4-diol 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: 92.0%

trityl chloride (76-83-5) + (2S,3S,4R)-2-azido-1,3,4-octadecanetriol (117168-59-9) → (2S,3S,4R)-2-azido-1-(trityloxy)octadecane-3,4-diol (160280-66-0)

Guidance literature:

With dmap; regioselective reaction;

DOI:10.1021/ol801663m

Reference yield:

(3aS,6R,6aS)-6-(hydroxymethyl)-2,2-dimethyl-tetrahydrofuro[3,4-d]-[1,3]dioxol-4-ol (4099-88-1,67814-68-0,70266-87-4,76249-50-8,76249-51-9,93451-15-1) → (2S,3S,4R)-2-azido-1-(trityloxy)octadecane-3,4-diol (160280-66-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: pyridine / 6 h / 80 °C

2.1: lithium hexamethyldisilazide / tetrahydrofuran / 1 h / 0 °C

2.2: 93 percent / lithium hexamethyldisilazide / tetrahydrofuran / 0 - 20 °C

3.1: 91 percent / hydrogen / palladium(II) hydroxide / ethyl acetate

4.1: 2,6-lutidine; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.5 h / -40 °C

5.1: 76 mg / tetramethylguanidinium azide / CH₂Cl₂ / -40 - 20 °C

6.1: 65 percent / acetic acid / methanol / 60 °C

7.1: pyridine

With pyridine; 2,6-dimethylpyridine; 4 A molecular sieve; hydrogen; acetic acid; tetramethylguanidinum azide; lithium hexamethyldisilazane; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; 2.2: Wittig reaction;

DOI:10.1016/j.tet.2004.12.027

Reference yield:

2,3-O-isopropylidene-5-O-triphenylmethyl-D-lyxofuranose → (2S,3S,4R)-2-azido-1-(trityloxy)octadecane-3,4-diol (160280-66-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: lithium hexamethyldisilazide / tetrahydrofuran / 1 h / 0 °C

1.2: 93 percent / lithium hexamethyldisilazide / tetrahydrofuran / 0 - 20 °C

2.1: 91 percent / hydrogen / palladium(II) hydroxide / ethyl acetate

3.1: 2,6-lutidine; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.5 h / -40 °C

4.1: 76 mg / tetramethylguanidinium azide / CH₂Cl₂ / -40 - 20 °C

5.1: 65 percent / acetic acid / methanol / 60 °C

6.1: pyridine

With pyridine; 2,6-dimethylpyridine; 4 A molecular sieve; hydrogen; acetic acid; tetramethylguanidinum azide; lithium hexamethyldisilazane; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; 1.2: Wittig reaction;

DOI:10.1016/j.tet.2004.12.027

upstream raw materials:

trityl chloride

(2S,3S,4R)-2-azido-1,3,4-octadecanetriol

(3aS,6R,6aS)-6-(hydroxymethyl)-2,2-dimethyl-tetrahydrofuro[3,4-d]-[1,3]dioxol-4-ol

3,4-O-isopropylidene-1-O-triphenylmethyl-D-arabino-octadec-5-en-1,2,3,4-tetraol

Downstream raw materials:

(2S,3S,4R)-2-azido-3,4-di-O-benzyl-1-O-trityl-1,3,4-octadecanetriol

(4S,5R)-4-((S)-1-Azido-2-trityloxy-ethyl)-5-tetradecyl-[1,3,2]dioxathiolane 2,2-dioxide

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

2-azido-sphingosine