allyl 2-O-(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl)-3,4-di-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranoside

Base Information

• Chemical Name: allyl 2-O-(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl)-3,4-di-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranoside
• CAS No.: 316382-37-3
• Molecular Formula: C₅₃H₅₈O₂₄
• Molecular Weight: 1079.03
• Mol file: 316382-37-3.mol

Synonyms:allyl 2-O-(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl)-3,4-di-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranoside

Chemical Property of allyl 2-O-(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl)-3,4-di-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl 2-O-(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl)-3,4-di-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranoside

There total 10 articles about allyl 2-O-(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl)-3,4-di-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-β-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: 95.0%

acetic anhydride (108-24-7) + allyl 2-O-(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl)-4-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranoside (316382-36-2) → allyl 2-O-(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl)-3,4-di-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranoside (316382-37-3)

Guidance literature:

With pyridine; at 20 ℃;

DOI:10.1016/S0008-6215(00)00185-3

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) → allyl 2-O-(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl)-3,4-di-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranoside (316382-37-3)

Guidance literature:

Multi-step reaction with 9 steps

1: 85 percent / NH₂NH₂; AcOH / 15 h / 20 °C

2: 53 percent / Ag₂O / toluene / 96 h / 20 °C

3: 100 percent / NaOMe / methanol

4: 50 percent / Hg(CN)2; HgBr₂ / acetonitrile / 15 h / 20 °C

5: 70 percent / camphosulfonic acid / acetone / 2 h

6: pyridine / CH₂Cl₂ / 24 h / 20 °C

7: 96 percent / tetrafluoroboric acid / acetonitrile; H₂O / 0 °C

8: 20 mg / Hg(CN)2 / toluene / 0.33 h / 20 °C

9: 95 percent / pyridine / 20 °C

With pyridine; tetrafluoroboric acid; camphor-10-sulfonic acid; sodium methylate; mercury(II) cyanide; acetic acid; mercury dibromide; silver(l) oxide; hydrazine; In methanol; dichloromethane; water; acetone; toluene; acetonitrile; 3: Zemplen deacetylation;

DOI:10.1016/S0008-6215(00)00185-3

Reference yield:

2,3,4,6-tetra-O-acetyl-D-mannopyranose (3947-62-4,6207-76-7,10343-06-3,19235-21-3,22554-70-7,22860-22-6,47339-09-3,57884-82-9,62057-79-8,70191-05-8,109525-54-4,140147-37-1) → allyl 2-O-(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl)-3,4-di-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranoside (316382-37-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 53 percent / Ag₂O / toluene / 96 h / 20 °C

2: 100 percent / NaOMe / methanol

3: 50 percent / Hg(CN)2; HgBr₂ / acetonitrile / 15 h / 20 °C

4: 70 percent / camphosulfonic acid / acetone / 2 h

5: pyridine / CH₂Cl₂ / 24 h / 20 °C

6: 96 percent / tetrafluoroboric acid / acetonitrile; H₂O / 0 °C

7: 20 mg / Hg(CN)2 / toluene / 0.33 h / 20 °C

8: 95 percent / pyridine / 20 °C

With pyridine; tetrafluoroboric acid; camphor-10-sulfonic acid; sodium methylate; mercury(II) cyanide; mercury dibromide; silver(l) oxide; In methanol; dichloromethane; water; acetone; toluene; acetonitrile; 2: Zemplen deacetylation;

DOI:10.1016/S0008-6215(00)00185-3

upstream raw materials:

acetic anhydride

allyl 2-O-(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl)-4-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranoside

D-Mannose pentaacetate

2,3,4,6-tetra-O-acetyl-D-mannopyranose