2-O-acetyl-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1-> 2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate

Base Information

• Chemical Name: 2-O-acetyl-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1-> 2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate
• CAS No.: 324041-20-5
• Molecular Formula: C₅₈H₄₈Cl₃NO₁₈
• Molecular Weight: 1153.37

Synonyms:2-O-acetyl-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1-> 2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate

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

Chemical Property:

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

There total 13 articles about 2-O-acetyl-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1-> 2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate 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: 86.0%

trichloroacetonitrile (545-06-2) + 2-O-acetyl-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-α-D-mannopyranose (684269-07-6) → 2-O-acetyl-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1-> 2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate (324041-20-5)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at -20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/ja204831z

Reference yield:

3,4,6-tri-O-benzoyl-α-D-mannopyranose 1,2-(allyl orthoacetate) (324041-18-1) → 2-O-acetyl-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1-> 2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate (324041-20-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 66 percent / TMSOTf / CH₂Cl₂ / 3 h / -42 °C

2: sodium acetate / PdCl₂ / acetic acid; H₂O / 12 h

3: 473 mg / DBU / CH₂Cl₂ / 2 h

With trimethylsilyl trifluoromethanesulfonate; sodium acetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium dichloride; In dichloromethane; water; acetic acid;

DOI:10.1081/SCC-120003613

Reference yield:

allyl (2-O-acetyl-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl)-(1->2)-3,4,6-tri-O-benzoyl-α-D-mannopyranoside (324041-19-2) → 2-O-acetyl-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1-> 2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate (324041-20-5)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium acetate / PdCl₂ / acetic acid; H₂O / 12 h

2: 473 mg / DBU / CH₂Cl₂ / 2 h

With sodium acetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium dichloride; In dichloromethane; water; acetic acid;

DOI:10.1081/SCC-120003613

upstream raw materials:

trichloroacetonitrile

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

1,2-O-(Allyloxyethyliden)-β-D-mannopyranose

3,4,6-tri-O-acetyl-1,2-O-(allyloxyethylidene)-β-D-mannopyranose

Downstream raw materials:

allyl 2-O-acetyl-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1->3)-4,6-O-benzylidene-α-D-mannopyranoside

2-O-acetyl-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1->3)-4,6-O-benzylidene-1,2-O-ethylidene-β-D-mannopyranose

allyl 2-O-acetyl-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1->3)-2-O-acetyl-4,6-O-benzylidene-α-D-mannopyranoside

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

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