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
• Mol file: 263247-10-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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%

dodecyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->2)-6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-β-D-galactopyranoside (263247-09-2) → dodecyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->2)-3,4-O-isopropylidene-β-D-galactopyranoside (263247-10-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 5h;

DOI:10.1016/S0008-6215(99)00252-9

Reference yield:

dodecyl 2,3,4,6-tetra-O-acetyl-α,β-D-glucopyranoside (66854-07-7,103129-55-1,117076-31-0) → dodecyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->2)-3,4-O-isopropylidene-β-D-galactopyranoside (263247-10-5)

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:

2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl bromide (42868-96-2) → dodecyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->2)-3,4-O-isopropylidene-β-D-galactopyranoside (263247-10-5)

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

upstream raw materials:

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

dodecyl 2,3,4,6-tetra-O-acetyl-α,β-D-glucopyranoside

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

1-dodecyl alcohol

Downstream raw materials:

dodecyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-acetyl-β-D-galactopyranosyl-(1->6)-[2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->2)]-3,4-isopropylidene-β-D-galactopyranoside

Refernces