ammonium allyl O-(β-D-manno-oct-2-ulopyranosylonic acid)-(1->6)-2-deoxy-2-<(3R)-3-hydroxytetradecanamido>-β-D-glucopyranoside 4-phosphate

Base Information

• Chemical Name: ammonium allyl O-(β-D-manno-oct-2-ulopyranosylonic acid)-(1->6)-2-deoxy-2-<(3R)-3-hydroxytetradecanamido>-β-D-glucopyranoside 4-phosphate
• CAS No.: 142236-33-7
• Molecular Formula: C₃₁H₅₆NO₁₇P*2H₃N
• Molecular Weight: 779.817
• Mol file: 142236-33-7.mol

Synonyms:

Chemical Property of ammonium allyl O-(β-D-manno-oct-2-ulopyranosylonic acid)-(1->6)-2-deoxy-2-<(3R)-3-hydroxytetradecanamido>-β-D-glucopyranoside 4-phosphate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ammonium allyl O-(β-D-manno-oct-2-ulopyranosylonic acid)-(1->6)-2-deoxy-2-<(3R)-3-hydroxytetradecanamido>-β-D-glucopyranoside 4-phosphate

There total 9 articles about ammonium allyl O-(β-D-manno-oct-2-ulopyranosylonic acid)-(1->6)-2-deoxy-2-<(3R)-3-hydroxytetradecanamido>-β-D-glucopyranoside 4-phosphate 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:

allyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside (63064-48-2,116288-58-5,117299-90-8,126778-02-7,28738-44-5) → ammonium allyl O-(β-D-manno-oct-2-ulopyranosylonic acid)-(1->6)-2-deoxy-2-<(3R)-3-hydroxytetradecanamido>-β-D-glucopyranoside 4-phosphate (142235-84-5,142236-33-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 100 percent / Ba(OH)2*8H₂O / H₂O / 110 °C

2: 87 percent / methanol / 48 h / Ambient temperature

3: 81 percent / 4-toluenesulphonic acid / tetrahydrofuran; acetonitrile / 1 h / Ambient temperature

4: 80 percent / 4-dimethylaminopyridine / pyridine / 30 °C

5: 94 percent / 1.5 M trifluoroacetic acid, silica gel / CH₂Cl₂ / 4 h / Ambient temperature

6: 65 percent / Hg(CN)2, MS 4A / acetonitrile / 0.25 h

7: 31 percent / N-methylimidazole / tetrahydrofuran / 60 °C

8: activated Zn, Ag₂CO₃ / pyridine; acetic acid / 18 h / Ambient temperature

9: 1) NaOMe, 2) 0.5 M NaOH / 1) 24 h, r.t., 2) H₂O, 2 h

With 1-methyl-1H-imidazole; dmap; barium dihydroxide; sodium hydroxide; sodium methylate; mercury(II) cyanide; silica gel; toluene-4-sulfonic acid; silver carbonate; trifluoroacetic acid; zinc; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; acetic acid; acetonitrile;

DOI:10.1016/S0008-6215(00)90547-0

Reference yield:

allyl 2-amino-2-deoxy-β-D-glucopyranoside (114244-98-3) → ammonium allyl O-(β-D-manno-oct-2-ulopyranosylonic acid)-(1->6)-2-deoxy-2-<(3R)-3-hydroxytetradecanamido>-β-D-glucopyranoside 4-phosphate (142235-84-5,142236-33-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 87 percent / methanol / 48 h / Ambient temperature

2: 81 percent / 4-toluenesulphonic acid / tetrahydrofuran; acetonitrile / 1 h / Ambient temperature

3: 80 percent / 4-dimethylaminopyridine / pyridine / 30 °C

4: 94 percent / 1.5 M trifluoroacetic acid, silica gel / CH₂Cl₂ / 4 h / Ambient temperature

5: 65 percent / Hg(CN)2, MS 4A / acetonitrile / 0.25 h

6: 31 percent / N-methylimidazole / tetrahydrofuran / 60 °C

7: activated Zn, Ag₂CO₃ / pyridine; acetic acid / 18 h / Ambient temperature

8: 1) NaOMe, 2) 0.5 M NaOH / 1) 24 h, r.t., 2) H₂O, 2 h

With 1-methyl-1H-imidazole; dmap; sodium hydroxide; sodium methylate; mercury(II) cyanide; silica gel; toluene-4-sulfonic acid; silver carbonate; trifluoroacetic acid; zinc; In tetrahydrofuran; pyridine; methanol; dichloromethane; acetic acid; acetonitrile;

DOI:10.1016/S0008-6215(00)90547-0

Reference yield:

Acetic acid (R)-1-[((2R,3R,4R,5S,6R)-2-allyloxy-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-ylcarbamoyl)-methyl]-dodecyl ester (142140-97-4) → ammonium allyl O-(β-D-manno-oct-2-ulopyranosylonic acid)-(1->6)-2-deoxy-2-<(3R)-3-hydroxytetradecanamido>-β-D-glucopyranoside 4-phosphate (142235-84-5,142236-33-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 81 percent / 4-toluenesulphonic acid / tetrahydrofuran; acetonitrile / 1 h / Ambient temperature

2: 80 percent / 4-dimethylaminopyridine / pyridine / 30 °C

3: 94 percent / 1.5 M trifluoroacetic acid, silica gel / CH₂Cl₂ / 4 h / Ambient temperature

4: 65 percent / Hg(CN)2, MS 4A / acetonitrile / 0.25 h

5: 31 percent / N-methylimidazole / tetrahydrofuran / 60 °C

6: activated Zn, Ag₂CO₃ / pyridine; acetic acid / 18 h / Ambient temperature

7: 1) NaOMe, 2) 0.5 M NaOH / 1) 24 h, r.t., 2) H₂O, 2 h

With 1-methyl-1H-imidazole; dmap; sodium hydroxide; sodium methylate; mercury(II) cyanide; silica gel; toluene-4-sulfonic acid; silver carbonate; trifluoroacetic acid; zinc; In tetrahydrofuran; pyridine; dichloromethane; acetic acid; acetonitrile;

DOI:10.1016/S0008-6215(00)90547-0

upstream raw materials:

(2S,4R,5R,6R)-4,5-Diacetoxy-2-[(2R,3S,4R,5R,6R)-5-((R)-3-acetoxy-tetradecanoylamino)-6-allyloxy-4-benzoyloxy-3-phosphonooxy-tetrahydro-pyran-2-ylmethoxy]-6-((R)-1,2-diacetoxy-ethyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

allyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside

allyl 2-amino-2-deoxy-β-D-glucopyranoside

Acetic acid (R)-1-[((2R,3R,4R,5S,6R)-2-allyloxy-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-ylcarbamoyl)-methyl]-dodecyl ester