Benzoic acid (E)-(R)-1-[(S)-1-azido-2-((2R,3R,4S,5R)-3,4,5-triacetoxy-tetrahydro-pyran-2-yloxy)-ethyl]-hexadec-2-enyl ester

Base Information

• Chemical Name: Benzoic acid (E)-(R)-1-[(S)-1-azido-2-((2R,3R,4S,5R)-3,4,5-triacetoxy-tetrahydro-pyran-2-yloxy)-ethyl]-hexadec-2-enyl ester
• CAS No.: 197144-03-9
• Molecular Formula: C₃₆H₅₃N₃O₁₀
• Molecular Weight: 687.831
• Mol file: 197144-03-9.mol

Synonyms:Benzoic acid (E)-(R)-1-[(S)-1-azido-2-((2R,3R,4S,5R)-3,4,5-triacetoxy-tetrahydro-pyran-2-yloxy)-ethyl]-hexadec-2-enyl ester

Chemical Property of Benzoic acid (E)-(R)-1-[(S)-1-azido-2-((2R,3R,4S,5R)-3,4,5-triacetoxy-tetrahydro-pyran-2-yloxy)-ethyl]-hexadec-2-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (E)-(R)-1-[(S)-1-azido-2-((2R,3R,4S,5R)-3,4,5-triacetoxy-tetrahydro-pyran-2-yloxy)-ethyl]-hexadec-2-enyl ester

There total 4 articles about Benzoic acid (E)-(R)-1-[(S)-1-azido-2-((2R,3R,4S,5R)-3,4,5-triacetoxy-tetrahydro-pyran-2-yloxy)-ethyl]-hexadec-2-enyl 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: 59.0%

(2S,3R,4E)-2-azido-3-benzoyloxy-4-octadecen-1-ol (103348-50-1) + 2,3,4-tri-O-acetyl-D-xylopyranosyl trichloroacetimidate (197144-02-8,869848-87-3) → Benzoic acid (E)-(R)-1-[(S)-1-azido-2-((2R,3R,4S,5R)-3,4,5-triacetoxy-tetrahydro-pyran-2-yloxy)-ethyl]-hexadec-2-enyl ester (197144-03-9)

Guidance literature:

With MS 300AW; boron trifluoride diethyl etherate; In dichloromethane; at -33 ℃; for 1.5h;

DOI:10.1021/jo970298k

Reference yield:

2,3,4-Tri-O-acetyl-D-xylopyranose (106820-14-8) → Benzoic acid (E)-(R)-1-[(S)-1-azido-2-((2R,3R,4S,5R)-3,4,5-triacetoxy-tetrahydro-pyran-2-yloxy)-ethyl]-hexadec-2-enyl ester (197144-03-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / DBU / CH₂Cl₂ / 1.25 h / 0 °C

2: 59 percent / BF₃*Et₂O, MS 300AW / CH₂Cl₂ / 1.5 h / -33 °C

With MS 300AW; boron trifluoride diethyl etherate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane;

DOI:10.1021/jo970298k

Reference yield:

Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yl ester (197143-93-4) → Benzoic acid (E)-(R)-1-[(S)-1-azido-2-((2R,3R,4S,5R)-3,4,5-triacetoxy-tetrahydro-pyran-2-yloxy)-ethyl]-hexadec-2-enyl ester (197144-03-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / CF₃COOH / CH₂Cl₂ / 1 h / Ambient temperature

2: 84 percent / DBU / CH₂Cl₂ / 1.25 h / 0 °C

3: 59 percent / BF₃*Et₂O, MS 300AW / CH₂Cl₂ / 1.5 h / -33 °C

With MS 300AW; boron trifluoride diethyl etherate; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/jo970298k

upstream raw materials:

(2S,3R,4E)-2-azido-3-benzoyloxy-4-octadecen-1-ol

2,3,4-tri-O-acetyl-D-xylopyranosyl trichloroacetimidate

2,3,4-Tri-O-acetyl-D-xylopyranose

Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yl ester

Downstream raw materials:

Benzoic acid (E)-(R)-1-[(S)-1-octadecanoylamino-2-((2R,3R,4S,5R)-3,4,5-triacetoxy-tetrahydro-pyran-2-yloxy)-ethyl]-hexadec-2-enyl ester