ethyl 2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl-(1->2)-[2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl-(1->3)]-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

Base Information

• Chemical Name: ethyl 2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl-(1->2)-[2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl-(1->3)]-4,6-O-benzylidene-1-thio-α-D-mannopyranoside
• CAS No.: 282088-50-0
• Molecular Formula: C₆₃H₇₆O₂₈S
• Molecular Weight: 1313.35
• Mol file: 282088-50-0.mol

Synonyms:ethyl 2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl-(1->2)-[2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl-(1->3)]-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

Chemical Property of ethyl 2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl-(1->2)-[2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl-(1->3)]-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl-(1->2)-[2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl-(1->3)]-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

There total 10 articles about ethyl 2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl-(1->2)-[2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl-(1->3)]-4,6-O-benzylidene-1-thio-α-D-mannopyranoside 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: 85.0%

phenyl 2,3,5,6-tetra-O-acetyl-β-D-selenogalactofuranoside (282088-49-7) + ethyl 2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl-(1->2)-4,6-O-benzylidene-1-thio-α-D-mannopyranoside (270917-79-8) → ethyl 2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl-(1->2)-[2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl-(1->3)]-4,6-O-benzylidene-1-thio-α-D-mannopyranoside (282088-50-0)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; In dichloromethane; at 0 ℃; for 0.666667h;

DOI:10.1016/S0008-6215(00)00007-0

Reference yield:

D-Mannose pentaacetate (83-87-4,604-68-2,604-69-3,2152-77-4,4026-35-1,4163-59-1,4163-60-4,4163-61-5,4163-65-9,4257-94-7,4257-96-9,16299-15-3,19186-39-1,19189-55-0,25878-60-8,25941-03-1,32445-48-0,32445-49-1,32445-53-7,32445-54-8,34685-58-0,34685-59-1,43168-42-9,43168-44-1,43169-22-8,43169-25-1,66966-07-2,70749-17-6,80184-01-6,93221-01-3,93221-02-4,99630-88-3,109215-53-4,115792-70-6,115792-73-9,139894-92-1,139973-25-4,144071-49-8,147648-81-5) → ethyl 2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl-(1->2)-[2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl-(1->3)]-4,6-O-benzylidene-1-thio-α-D-mannopyranoside (282088-50-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 50 percent H₃PO₂ / Heating

1.2: 49 percent / BF₃*OEt₂ / CH₂Cl₂

2.1: MeONa / methanol

3.1: p-TsOH / dimethylformamide / 1.5 h / 45 - 50 °C

4.1: 68 percent / (Bu₄)NHSO₄; 5 percent aq. NaOH / CH₂Cl₂ / 40 h / Heating

5.1: 86 percent / DMAP / pyridine / 20 °C

6.1: 60 percent / molecular sieves (4 Angstroem); N-iodosuccinimide; trifluoromethanesulfonic acid / CH₂Cl₂ / 1.5 h / 0 °C

7.1: 96 percent / MeONa / methanol / 20 °C

8.1: 85 percent / molecular sieves (4 Angstroem); N-iodosuccinimide; trifluoromethanesulfonic acid / CH₂Cl₂ / 0.67 h / 0 °C

With dmap; sodium hydroxide; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; sodium methylate; tetra(n-butyl)ammonium hydrogensulfate; hypophosphorous acid; toluene-4-sulfonic acid; In pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Reduction / 1.2: glycosylation / 2.1: Deacetylation / 3.1: trans-acetalization / 4.1: benzylation / 5.1: Acylation / 6.1: glycosylation / 7.1: debenzoylation / 8.1: glycosylation;

DOI:10.1016/S0008-6215(00)00007-0

Reference yield:

S-ethyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside (142924-31-0) → ethyl 2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl-(1->2)-[2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl-(1->3)]-4,6-O-benzylidene-1-thio-α-D-mannopyranoside (282088-50-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 69 percent / pyridine / 4 h / -25 °C

2: 60 percent / molecular sieves (4 Angstroem); N-iodosuccinimide; trifluoromethanesulfonic acid / CH₂Cl₂ / 1.5 h / 0 °C

3: 96 percent / MeONa / methanol / 20 °C

4: 85 percent / molecular sieves (4 Angstroem); N-iodosuccinimide; trifluoromethanesulfonic acid / CH₂Cl₂ / 0.67 h / 0 °C

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; sodium methylate; In pyridine; methanol; dichloromethane; 1: benzoylation / 2: glycosylation / 3: debenzoylation / 4: glycosylation;

DOI:10.1016/S0008-6215(00)00007-0

upstream raw materials:

phenyl 2,3,5,6-tetra-O-acetyl-β-D-selenogalactofuranoside

ethyl 2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl-(1->2)-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

D-Mannose pentaacetate

S-ethyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside