(2S,3S,4R)-2--3,4-di-O-benzoyl-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-1,3,4-undecanetriol

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Chemical Name:(2S,3S,4R)-2--3,4-di-O-benzoyl-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-1,3,4-undecanetriol
CAS No.:164989-20-2
Molecular Formula:C₈₅H₁₁₅NO₁₃
Molecular Weight:1358.85
Hs Code.:

(2S,3S,4R)-2-<N-((R)-2-acetoxyteracosanoyl)amino>-3,4-di-O-benzoyl-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-1,3,4-undecanetriol

Synonyms:(2S,3S,4R)-2--3,4-di-O-benzoyl-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-1,3,4-undecanetriol

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Chemical Property of (2S,3S,4R)-2--3,4-di-O-benzoyl-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-1,3,4-undecanetriol

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Technology Process of (2S,3S,4R)-2--3,4-di-O-benzoyl-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-1,3,4-undecanetriol

There total 14 articles about (2S,3S,4R)-2--3,4-di-O-benzoyl-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-1,3,4-undecanetriol 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:

: 111-25-1
1-bromo-hexane

: 164989-20-2
(2S,3S,4R)-2--3,4-di-O-benzoyl-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-1,3,4-undecanetriol

Guidance literature:: Multi-step reaction with 12 steps

1: 12 h / 150 °C

2: 1.) nBuLi / 1.) hexane, THF, -10 deg C, 30 min, 2.) hexane, THF, RT, 16 h

3: 88 percent / H₂ / 10percent Pd/C / tetrahydrofuran / 16 h

4: 92 percent / pyridine / 1.5 h / 20 °C

5: 79 percent / NaN₃ / dimethylformamide / 16 h / 100 °C

6: H₂ / 10percent Pd/C / tetrahydrofuran / 16 h / Ambient temperature

7: 2-chloro-1-methylpyridinium iodide, n-tributylamine / CH₂Cl₂ / 2 h / Heating

8: 88 percent / H₂ / Pd / tetrahydrofuran; propan-1-ol / 16 h / 40 °C

9: 85 percent / pyridine, 4-(dimethylamino)pyridine / 3 h / 40 °C

10: 90 percent / pyridine, 4-(dimethylamino)pyridine / 12 h / Ambient temperature

11: 88 percent / pTsOH*H₂O / CH₂Cl₂; methanol / 2 h / Ambient temperature

12: 1.) SnCl₂, AgClO₄, 4 Angstroem sieves / 1.) THF, RT, 30 min, 2.) THF, RT, 2 h

With pyridine; dmap; n-butyllithium; sodium azide; tributyl-amine; 4 A molecular sieve; 2-chloro-1-methyl-pyridinium iodide; hydrogen; silver perchlorate; toluene-4-sulfonic acid; tin(ll) chloride; palladium on activated charcoal; palladium; In tetrahydrofuran; methanol; propan-1-ol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm00012a018

Reference yield:

: 20672-66-6,40246-26-2,84926-76-1,114179-79-2,115184-49-1
3,4,5-tri-O-benzyl-D-galactopyranose

: 164989-20-2
(2S,3S,4R)-2--3,4-di-O-benzoyl-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-1,3,4-undecanetriol

Guidance literature:: Multi-step reaction with 12 steps

1: NaIO₄ / ethanol; H₂O / 16 h / -5 - 20 °C

2: 1.) nBuLi / 1.) hexane, THF, -10 deg C, 30 min, 2.) hexane, THF, RT, 16 h

3: 88 percent / H₂ / 10percent Pd/C / tetrahydrofuran / 16 h

4: 92 percent / pyridine / 1.5 h / 20 °C

5: 79 percent / NaN₃ / dimethylformamide / 16 h / 100 °C

6: H₂ / 10percent Pd/C / tetrahydrofuran / 16 h / Ambient temperature

7: 2-chloro-1-methylpyridinium iodide, n-tributylamine / CH₂Cl₂ / 2 h / Heating

8: 88 percent / H₂ / Pd / tetrahydrofuran; propan-1-ol / 16 h / 40 °C

9: 85 percent / pyridine, 4-(dimethylamino)pyridine / 3 h / 40 °C

10: 90 percent / pyridine, 4-(dimethylamino)pyridine / 12 h / Ambient temperature

11: 88 percent / pTsOH*H₂O / CH₂Cl₂; methanol / 2 h / Ambient temperature

12: 1.) SnCl₂, AgClO₄, 4 Angstroem sieves / 1.) THF, RT, 30 min, 2.) THF, RT, 2 h

With pyridine; dmap; sodium periodate; n-butyllithium; sodium azide; tributyl-amine; 4 A molecular sieve; 2-chloro-1-methyl-pyridinium iodide; hydrogen; silver perchlorate; toluene-4-sulfonic acid; tin(ll) chloride; palladium on activated charcoal; palladium; In tetrahydrofuran; methanol; propan-1-ol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jm00012a018

Reference yield:

: 4762-26-9
hexyltriphenylphosphonium bromide

: 164989-20-2
(2S,3S,4R)-2--3,4-di-O-benzoyl-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-1,3,4-undecanetriol

Guidance literature:: Multi-step reaction with 11 steps

1: 1.) nBuLi / 1.) hexane, THF, -10 deg C, 30 min, 2.) hexane, THF, RT, 16 h

2: 88 percent / H₂ / 10percent Pd/C / tetrahydrofuran / 16 h

3: 92 percent / pyridine / 1.5 h / 20 °C

4: 79 percent / NaN₃ / dimethylformamide / 16 h / 100 °C

5: H₂ / 10percent Pd/C / tetrahydrofuran / 16 h / Ambient temperature

6: 2-chloro-1-methylpyridinium iodide, n-tributylamine / CH₂Cl₂ / 2 h / Heating

7: 88 percent / H₂ / Pd / tetrahydrofuran; propan-1-ol / 16 h / 40 °C

8: 85 percent / pyridine, 4-(dimethylamino)pyridine / 3 h / 40 °C

9: 90 percent / pyridine, 4-(dimethylamino)pyridine / 12 h / Ambient temperature

10: 88 percent / pTsOH*H₂O / CH₂Cl₂; methanol / 2 h / Ambient temperature

11: 1.) SnCl₂, AgClO₄, 4 Angstroem sieves / 1.) THF, RT, 30 min, 2.) THF, RT, 2 h

With pyridine; dmap; n-butyllithium; sodium azide; tributyl-amine; 4 A molecular sieve; 2-chloro-1-methyl-pyridinium iodide; hydrogen; silver perchlorate; toluene-4-sulfonic acid; tin(ll) chloride; palladium on activated charcoal; palladium; In tetrahydrofuran; methanol; propan-1-ol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm00012a018