1-O-(4,6-O-benzylidene-2,3-di-O-dodecanoyl-β-D-mannopyranosyl)-3-O-tert-butyldimethylsilyl-2,4-O-ethylidene-D-erythritol

Base Information

Chemical Name:1-O-(4,6-O-benzylidene-2,3-di-O-dodecanoyl-β-D-mannopyranosyl)-3-O-tert-butyldimethylsilyl-2,4-O-ethylidene-D-erythritol
CAS No.:407616-90-4
Molecular Formula:C₄₉H₈₄O₁₁Si
Molecular Weight:877.285
Hs Code.:

Synonyms:1-O-(4,6-O-benzylidene-2,3-di-O-dodecanoyl-β-D-mannopyranosyl)-3-O-tert-butyldimethylsilyl-2,4-O-ethylidene-D-erythritol

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Chemical Property of 1-O-(4,6-O-benzylidene-2,3-di-O-dodecanoyl-β-D-mannopyranosyl)-3-O-tert-butyldimethylsilyl-2,4-O-ethylidene-D-erythritol

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Technology Process of 1-O-(4,6-O-benzylidene-2,3-di-O-dodecanoyl-β-D-mannopyranosyl)-3-O-tert-butyldimethylsilyl-2,4-O-ethylidene-D-erythritol

There total 15 articles about 1-O-(4,6-O-benzylidene-2,3-di-O-dodecanoyl-β-D-mannopyranosyl)-3-O-tert-butyldimethylsilyl-2,4-O-ethylidene-D-erythritol 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: 91.0%

: 112-16-3
n-dodecanoyl chloride

: 407616-89-1
1-O-(4,6-O-benzylidene-β-D-mannopyranosyl)-3-O-tert-butyldimethylsilyl-2,4-O-ethylidene-D-erythritol

: 407616-90-4
1-O-(4,6-O-benzylidene-2,3-di-O-dodecanoyl-β-D-mannopyranosyl)-3-O-tert-butyldimethylsilyl-2,4-O-ethylidene-D-erythritol

Guidance literature:: With pyridine; dmap; In dichloromethane; at 20 ℃; for 5h;
DOI:10.1016/S0040-4020(01)01087-0

Reference yield:

: 159407-19-9
phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside

: 407616-90-4
1-O-(4,6-O-benzylidene-2,3-di-O-dodecanoyl-β-D-mannopyranosyl)-3-O-tert-butyldimethylsilyl-2,4-O-ethylidene-D-erythritol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 98 percent / NaH / dimethylformamide / 3 h / 20 °C

2.1: 1-(benzenesulfinyl)piperidine; 2,4,6-tri-tert-butylpyrimidine; 3 Angstroem molecular sieves / triflic anhydride / CH₂Cl₂ / 0.08 h / -60 °C

2.2: 66 percent / CH₂Cl₂ / -60 - 20 °C

3.1: 96 percent / 3 Angstroem molecular sieves; H₂ / [(1,5-cyclooctadiene)Ir(PPh₂Me)2]PF₆ / tetrahydrofuran / 24 h / 20 °C

4.1: 92 percent / water; HgO; HgCl₂ / acetone / 2 h / 20 °C

5.1: 91 percent / DMAP; pyridine / CH₂Cl₂ / 5 h / 20 °C

With pyridine; dmap; 1-benzenesulfinyl piperidine; 3 A molecular sieve; water; hydrogen; sodium hydride; mercury dichloride; mercury(II) oxide; 2,4,6-tri-tert-butylpyrimidine; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; trifluoromethylsulfonic anhydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0040-4020(01)01087-0

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 407616-90-4
1-O-(4,6-O-benzylidene-2,3-di-O-dodecanoyl-β-D-mannopyranosyl)-3-O-tert-butyldimethylsilyl-2,4-O-ethylidene-D-erythritol

Guidance literature:: Multi-step reaction with 7 steps

1.1: 96 percent / imidazole / dimethylformamide / 3 h / 46 °C

2.1: 86 percent / NBS; water / acetonitrile / 0.5 h / -20 °C

3.1: 80 percent / sodium borohydride / CH₂Cl₂; ethanol / 2 h / 20 °C

4.1: 1-(benzenesulfinyl)piperidine; 2,4,6-tri-tert-butylpyrimidine; 3 Angstroem molecular sieves / triflic anhydride / CH₂Cl₂ / 0.08 h / -60 °C

4.2: 66 percent / CH₂Cl₂ / -60 - 20 °C

5.1: 96 percent / 3 Angstroem molecular sieves; H₂ / [(1,5-cyclooctadiene)Ir(PPh₂Me)2]PF₆ / tetrahydrofuran / 24 h / 20 °C

6.1: 92 percent / water; HgO; HgCl₂ / acetone / 2 h / 20 °C

7.1: 91 percent / DMAP; pyridine / CH₂Cl₂ / 5 h / 20 °C

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; N-Bromosuccinimide; 1-benzenesulfinyl piperidine; 3 A molecular sieve; water; hydrogen; mercury dichloride; mercury(II) oxide; 2,4,6-tri-tert-butylpyrimidine; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; trifluoromethylsulfonic anhydride; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile;
DOI:10.1016/S0040-4020(01)01087-0