(2,3,4-tri-O-acetyl-6-azido-α-D-mannopyranosyl)-(1->2)-allyl-3,4-di-O-benzoyl-6-azido-α-D-mannopyranose

Base Information

• Chemical Name: (2,3,4-tri-O-acetyl-6-azido-α-D-mannopyranosyl)-(1->2)-allyl-3,4-di-O-benzoyl-6-azido-α-D-mannopyranose
• CAS No.: 1333231-19-8
• Molecular Formula: C₃₅H₃₈N₆O₁₄
• Molecular Weight: 766.719
• Mol file: 1333231-19-8.mol

Synonyms:(2,3,4-tri-O-acetyl-6-azido-α-D-mannopyranosyl)-(1->2)-allyl-3,4-di-O-benzoyl-6-azido-α-D-mannopyranose

Chemical Property of (2,3,4-tri-O-acetyl-6-azido-α-D-mannopyranosyl)-(1->2)-allyl-3,4-di-O-benzoyl-6-azido-α-D-mannopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2,3,4-tri-O-acetyl-6-azido-α-D-mannopyranosyl)-(1->2)-allyl-3,4-di-O-benzoyl-6-azido-α-D-mannopyranose

There total 13 articles about (2,3,4-tri-O-acetyl-6-azido-α-D-mannopyranosyl)-(1->2)-allyl-3,4-di-O-benzoyl-6-azido-α-D-mannopyranose 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: 72.0%

2,3,4-tri-O-acetyl-6-azido-α-D-mannopyranosyl trichloroacetimidate (1333231-16-5) + allyl 3,4-di-O-benzoyl-6-azido-α-D-mannopyranoside (1333231-14-3) → (2,3,4-tri-O-acetyl-6-azido-α-D-mannopyranosyl)-(1->2)-allyl-3,4-di-O-benzoyl-6-azido-α-D-mannopyranose (1333231-19-8)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -30 - 20 ℃; Inert atmosphere;

DOI:10.1039/c1cc13213j

Reference yield:

3,4-di-O-acetyl-6-O-tosyl-1,2-O-ethylidene-β-D-mannopyranoside (1333231-07-4) → (2,3,4-tri-O-acetyl-6-azido-α-D-mannopyranosyl)-(1->2)-allyl-3,4-di-O-benzoyl-6-azido-α-D-mannopyranose (1333231-19-8)

Guidance literature:

Multi-step reaction with 8 steps

1: sodium azide / N,N-dimethyl-formamide / Inert atmosphere

2: sodium methylate / methanol / 4 h / 20 °C / Inert atmosphere

3: pyridine / Inert atmosphere

4: trifluoroacetic acid / water / Inert atmosphere

5: pyridine / Inert atmosphere

6: boron trifluoride diethyl etherate / dichloromethane / 0 - 20 °C / Inert atmosphere

7: methanol; acetyl chloride / dichloromethane / Inert atmosphere

8: trimethylsilyl trifluoromethanesulfonate / dichloromethane / -30 - 20 °C / Inert atmosphere

With pyridine; methanol; sodium azide; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; sodium methylate; acetyl chloride; trifluoroacetic acid; In methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1039/c1cc13213j

Reference yield:

3,4-di-O-acetyl-6-azido-1,2-O-ethylidene-β-D-mannopyranoside (1333231-08-5) → (2,3,4-tri-O-acetyl-6-azido-α-D-mannopyranosyl)-(1->2)-allyl-3,4-di-O-benzoyl-6-azido-α-D-mannopyranose (1333231-19-8)

Guidance literature:

Multi-step reaction with 7 steps

1: sodium methylate / methanol / 4 h / 20 °C / Inert atmosphere

2: pyridine / Inert atmosphere

3: trifluoroacetic acid / water / Inert atmosphere

4: pyridine / Inert atmosphere

5: boron trifluoride diethyl etherate / dichloromethane / 0 - 20 °C / Inert atmosphere

6: methanol; acetyl chloride / dichloromethane / Inert atmosphere

7: trimethylsilyl trifluoromethanesulfonate / dichloromethane / -30 - 20 °C / Inert atmosphere

With pyridine; methanol; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; sodium methylate; acetyl chloride; trifluoroacetic acid; In methanol; dichloromethane; water;

DOI:10.1039/c1cc13213j

upstream raw materials:

2,3,4-tri-O-acetyl-6-azido-6-deoxy-α-D-mannopyranose

3,4-di-O-acetyl-6-O-tosyl-1,2-O-ethylidene-β-D-mannopyranoside

3,4-di-O-acetyl-6-azido-1,2-O-ethylidene-β-D-mannopyranoside

6-azido-1,2-O-ethylidene-β-D-mannopyranoside

Downstream raw materials:

(2,3,4-tri-O-acetyl-6-azido-α-D-mannopyranosyl)-(1->2)-carboxymethyl-3,4-di-O-benzoyl-6-azido-α-D-mannopyranose