O-(2-O-acetyl-3,4,6-tri-O-benzyl-α/β-D-mannopyranosyl)trichloroacetimidate

Base Information

• Chemical Name: O-(2-O-acetyl-3,4,6-tri-O-benzyl-α/β-D-mannopyranosyl)trichloroacetimidate
• CAS No.: 187226-47-7
• Molecular Formula: C₃₁H₃₂Cl₃NO₇
• Molecular Weight: 636.957
• Mol file: 187226-47-7.mol

Synonyms:O-(2-O-acetyl-3,4,6-tri-O-benzyl-α/β-D-mannopyranosyl)trichloroacetimidate

Chemical Property of O-(2-O-acetyl-3,4,6-tri-O-benzyl-α/β-D-mannopyranosyl)trichloroacetimidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O-(2-O-acetyl-3,4,6-tri-O-benzyl-α/β-D-mannopyranosyl)trichloroacetimidate

There total 7 articles about O-(2-O-acetyl-3,4,6-tri-O-benzyl-α/β-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: 90.2%

2-O-acetyl-3,4,6-tri-O-benzyl-D-mannopyranoside (129214-38-6) + trichloroacetonitrile (545-06-2) → O-(2-O-acetyl-3,4,6-tri-O-benzyl-α/β-D-mannopyranosyl)trichloroacetimidate (187226-47-7)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 - 4 ℃; for 1h;

DOI:10.1016/S0008-6215(99)00107-X

Reference yield:

3,4,6-tri-O-acetyl-1,2-O-<1-(R)-methoxyethylidene>-β-D-mannopyranose (80877-03-8) → O-(2-O-acetyl-3,4,6-tri-O-benzyl-α/β-D-mannopyranosyl)trichloroacetimidate (187226-47-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: NH₃ / methanol / 20 °C

2.1: sodium hydride / dimethylformamide / 30 h

2.2: dimethylformamide / 20 °C

3.1: 92.5 percent / AcOH / H₂O / 24 h / 20 °C

4.1: 90.2 percent / DBU / CH₂Cl₂ / 1 h / 0 - 4 °C

With ammonia; sodium hydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane; water; N,N-dimethyl-formamide; 1.1: Deacetylation / 2.1: Metallation / 2.2: Etherification / 3.1: Ring cleavage / 4.1: Esterification;

DOI:10.1016/S0008-6215(99)00107-X

Reference yield:

3,4,6-tri-O-benzyl-1,2-O-<1-(R)-methoxyethylidene>-β-D-mannopyranose (68681-00-5) → O-(2-O-acetyl-3,4,6-tri-O-benzyl-α/β-D-mannopyranosyl)trichloroacetimidate (187226-47-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 92.5 percent / AcOH / H₂O / 24 h / 20 °C

2: 90.2 percent / DBU / CH₂Cl₂ / 1 h / 0 - 4 °C

With acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; water; 1: Ring cleavage / 2: Esterification;

DOI:10.1016/S0008-6215(99)00107-X

upstream raw materials:

2-O-acetyl-3,4,6-tri-O-benzyl-D-mannopyranoside

trichloroacetonitrile

3,4,6-tri-O-acetyl-1,2-O-<1-(R)-methoxyethylidene>-β-D-mannopyranose

3,4,6-tri-O-benzyl-1,2-O-<1-(R)-methoxyethylidene>-β-D-mannopyranose

Downstream raw materials:

Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((R)-3-hexadecyloxy-2-methoxy-propoxy)-tetrahydro-pyran-3-yl ester

methyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-mannopyranoside

3-O-acetyl-6-O-allyl-4,5-di-O-benzyl-1-O-(1R)-menthyloxycarbonyl-2-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-D-myo-inositol

phenyl (2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-2-O-acetyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside