dodecyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->2)-3,4-O-isopropylidene-β-D-galactopyranoside

Base Information

Chemical Name:dodecyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->2)-3,4-O-isopropylidene-β-D-galactopyranoside
CAS No.:263247-10-5
Molecular Formula:C₄₇H₆₀O₁₃
Molecular Weight:832.986
Hs Code.:

Synonyms:dodecyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->2)-3,4-O-isopropylidene-β-D-galactopyranoside

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Chemical Property of dodecyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->2)-3,4-O-isopropylidene-β-D-galactopyranoside

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Technology Process of dodecyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->2)-3,4-O-isopropylidene-β-D-galactopyranoside

There total 9 articles about dodecyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->2)-3,4-O-isopropylidene-β-D-galactopyranoside 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: 95.0%

: 263247-09-2
dodecyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->2)-6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-β-D-galactopyranoside

: 263247-10-5
dodecyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->2)-3,4-O-isopropylidene-β-D-galactopyranoside

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 5h;
DOI:10.1016/S0008-6215(99)00252-9

Reference yield:

: 66854-07-7,103129-55-1,117076-31-0
dodecyl 2,3,4,6-tetra-O-acetyl-α,β-D-glucopyranoside

: 263247-10-5
dodecyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->2)-3,4-O-isopropylidene-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 1.7 g / NaOMe / methanol / 6 h / 20 °C

2: 80 percent / p-toluenesulfonic acid monohydrate / acetone / 16 h / 20 °C

3: 91 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 16 h / 20 °C

4: 87 percent / Me₃SiOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / -15 °C

5: 95 percent / n-Bu₄NF trihydrate / tetrahydrofuran / 5 h / 20 °C

With dmap; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium methylate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; acetone; 1: Zemplen deacetylation / 2: Substitution / 3: Substitution / 4: glycosylation / 5: Elimination;
DOI:10.1016/S0008-6215(99)00252-9

Reference yield:

: 42868-96-2
2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl bromide

: 263247-10-5
dodecyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->2)-3,4-O-isopropylidene-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: silver carbonate / acetone; H₂O / 16 h / 20 °C

1.2: 79 percent / K₂CO₃ / CH₂Cl₂ / 8 h / 20 °C

2.1: 87 percent / Me₃SiOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / -15 °C

3.1: 95 percent / n-Bu₄NF trihydrate / tetrahydrofuran / 5 h / 20 °C

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetrabutyl ammonium fluoride; silver carbonate; In tetrahydrofuran; dichloromethane; water; acetone; 1.1: Dehalogenation / 1.2: Schmidt activation / 2.1: glycosylation / 3.1: Elimination;
DOI:10.1016/S0008-6215(99)00252-9