Benzoic acid (E)-(S)-1-{(S)-1-azido-2-[(2R,3R,4S,5R,6R)-3,4-diacetoxy-6-acetoxymethyl-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-ethyl}-hexadec-2-enyl ester

Base Information

• Chemical Name: Benzoic acid (E)-(S)-1-{(S)-1-azido-2-[(2R,3R,4S,5R,6R)-3,4-diacetoxy-6-acetoxymethyl-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-ethyl}-hexadec-2-enyl ester
• CAS No.: 928302-19-6
• Molecular Formula: C₅₁H₇₃N₃O₂₀
• Molecular Weight: 1048.15

Synonyms:

Chemical Property of Benzoic acid (E)-(S)-1-{(S)-1-azido-2-[(2R,3R,4S,5R,6R)-3,4-diacetoxy-6-acetoxymethyl-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-ethyl}-hexadec-2-enyl ester

Chemical Property:

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Technology Process of Benzoic acid (E)-(S)-1-{(S)-1-azido-2-[(2R,3R,4S,5R,6R)-3,4-diacetoxy-6-acetoxymethyl-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-ethyl}-hexadec-2-enyl ester

There total 5 articles about Benzoic acid (E)-(S)-1-{(S)-1-azido-2-[(2R,3R,4S,5R,6R)-3,4-diacetoxy-6-acetoxymethyl-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-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: 30.0%

(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl trichloroacetimidate (106256-89-7) + (2S,3R,4E)-2-Azido-3-O-benzoyl-4-octadecene-1,3-diol (928302-17-4) → Benzoic acid (E)-(S)-1-{(S)-1-azido-2-[(2R,3R,4S,5R,6R)-3,4-diacetoxy-6-acetoxymethyl-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-ethyl}-hexadec-2-enyl ester (928302-19-6)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane;

DOI:10.1016/j.chemphyslip.2006.03.001

Reference yield:

2-azido-1-(tert-butyldiphenylsilanyloxy)-L-threo-sphingosine (928302-15-2) → Benzoic acid (E)-(S)-1-{(S)-1-azido-2-[(2R,3R,4S,5R,6R)-3,4-diacetoxy-6-acetoxymethyl-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-ethyl}-hexadec-2-enyl ester (928302-19-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / 4-(dimethylamino)pyridine / CH₂Cl₂

2: 63 percent / imidazole; TBAF / tetrahydrofuran / 3 h / -23 °C

3: 30 percent / BF₃*Et₂O / CH₂Cl₂

With 1H-imidazole; dmap; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.chemphyslip.2006.03.001

Reference yield:

2-azido-3-benzoyl-1-(tert-butyldiphenylsilyloxy)-L-threo-sphingosine (928302-16-3) → Benzoic acid (E)-(S)-1-{(S)-1-azido-2-[(2R,3R,4S,5R,6R)-3,4-diacetoxy-6-acetoxymethyl-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-ethyl}-hexadec-2-enyl ester (928302-19-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 63 percent / imidazole; TBAF / tetrahydrofuran / 3 h / -23 °C

2: 30 percent / BF₃*Et₂O / CH₂Cl₂

With 1H-imidazole; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.chemphyslip.2006.03.001

upstream raw materials:

(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl trichloroacetimidate

(2S,3R,4E)-2-Azido-3-O-benzoyl-4-octadecene-1,3-diol

2-azido-1-(tert-butyldiphenylsilanyloxy)-L-threo-sphingosine

2-azido-3-benzoyl-1-(tert-butyldiphenylsilyloxy)-L-threo-sphingosine

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