2-O-benzoyl-4,6-O-benzylidene-3-O-methyl-1-thio-α-D-mannopyranosyl-(1-6)-2-Obenzoyl-4-O-benzyl-3-O-methyl-1-thio-α-D-mannopyranosyl trichloroacetamidate

Base Information

• Chemical Name: 2-O-benzoyl-4,6-O-benzylidene-3-O-methyl-1-thio-α-D-mannopyranosyl-(1-6)-2-Obenzoyl-4-O-benzyl-3-O-methyl-1-thio-α-D-mannopyranosyl trichloroacetamidate
• CAS No.: 1599455-71-6
• Molecular Formula: C₄₄H₄₄Cl₃NO₁₃
• Molecular Weight: 901.191

Synonyms:2-O-benzoyl-4,6-O-benzylidene-3-O-methyl-1-thio-α-D-mannopyranosyl-(1-6)-2-Obenzoyl-4-O-benzyl-3-O-methyl-1-thio-α-D-mannopyranosyl trichloroacetamidate

Chemical Property of 2-O-benzoyl-4,6-O-benzylidene-3-O-methyl-1-thio-α-D-mannopyranosyl-(1-6)-2-Obenzoyl-4-O-benzyl-3-O-methyl-1-thio-α-D-mannopyranosyl trichloroacetamidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of 2-O-benzoyl-4,6-O-benzylidene-3-O-methyl-1-thio-α-D-mannopyranosyl-(1-6)-2-Obenzoyl-4-O-benzyl-3-O-methyl-1-thio-α-D-mannopyranosyl trichloroacetamidate

There total 6 articles about 2-O-benzoyl-4,6-O-benzylidene-3-O-methyl-1-thio-α-D-mannopyranosyl-(1-6)-2-Obenzoyl-4-O-benzyl-3-O-methyl-1-thio-α-D-mannopyranosyl trichloroacetamidate 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: 89.0%

phenyl-4,6-O-benzylidene-2-O-benzoyl-3-O-methyl-1-thio-α-D-mannopyranosyl-(1-6)-2-O-benzoyl-4-O-benzyl-3-O-methyl-1-thio-α-D-mannopyranoside (1599455-70-5) + trichloroacetonitrile (545-06-2) → 2-O-benzoyl-4,6-O-benzylidene-3-O-methyl-1-thio-α-D-mannopyranosyl-(1-6)-2-Obenzoyl-4-O-benzyl-3-O-methyl-1-thio-α-D-mannopyranosyl trichloroacetamidate (1599455-71-6)

Guidance literature:

phenyl-4,6-O-benzylidene-2-O-benzoyl-3-O-methyl-1-thio-α-D-mannopyranosyl-(1-6)-2-O-benzoyl-4-O-benzyl-3-O-methyl-1-thio-α-D-mannopyranoside; With N-Bromosuccinimide; In water; acetone; at 0 ℃; for 0.5h; Inert atmosphere;

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

DOI:10.1002/chem.201304950

Reference yield:

(2R,3S,4S,5S,6R)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol (2936-70-1,5624-48-6,13992-15-9,16758-34-2,28244-97-5,77481-63-1,105088-17-3,149495-84-1,77481-62-0) → 2-O-benzoyl-4,6-O-benzylidene-3-O-methyl-1-thio-α-D-mannopyranosyl-(1-6)-2-Obenzoyl-4-O-benzyl-3-O-methyl-1-thio-α-D-mannopyranosyl trichloroacetamidate (1599455-71-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: (1S)-10-camphorsulfonic acid / acetonitrile / 0.17 h / 20 °C / Inert atmosphere

2.1: di(n-butyl)tin oxide / toluene / 4 h / 110 °C / Reflux; Inert atmosphere

2.2: 50 °C

3.1: pyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

4.1: bromine / dichloromethane / 1 h / 20 °C / Inert atmosphere

4.2: 2 h / -35 °C / Inert atmosphere; Molecular sieve

5.1: N-Bromosuccinimide / water; acetone / 0.5 h / 0 °C / Inert atmosphere

5.2: 1 h / 20 °C / Inert atmosphere

With pyridine; N-Bromosuccinimide; (1S)-10-camphorsulfonic acid; bromine; di(n-butyl)tin oxide; In dichloromethane; water; acetone; toluene; acetonitrile;

DOI:10.1002/chem.201304950

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → 2-O-benzoyl-4,6-O-benzylidene-3-O-methyl-1-thio-α-D-mannopyranosyl-(1-6)-2-Obenzoyl-4-O-benzyl-3-O-methyl-1-thio-α-D-mannopyranosyl trichloroacetamidate (1599455-71-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: (1S)-10-camphorsulfonic acid / acetonitrile / 0.17 h / 20 °C / Inert atmosphere

2.1: di(n-butyl)tin oxide / toluene / 4 h / 110 °C / Reflux; Inert atmosphere

2.2: 50 °C

3.1: pyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

4.1: bromine / dichloromethane / 1 h / 20 °C / Inert atmosphere

4.2: 2 h / -35 °C / Inert atmosphere; Molecular sieve

5.1: N-Bromosuccinimide / water; acetone / 0.5 h / 0 °C / Inert atmosphere

5.2: 1 h / 20 °C / Inert atmosphere

With pyridine; N-Bromosuccinimide; (1S)-10-camphorsulfonic acid; bromine; di(n-butyl)tin oxide; In dichloromethane; water; acetone; toluene; acetonitrile;

DOI:10.1002/chem.201304950

upstream raw materials:

phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside

phenyl 4,6-O-benzylidene-3-O-methyl-1-thio-α-D-mannopyranoside

(2R,3S,4S,5S,6R)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol

benzaldehyde dimethyl acetal

Downstream raw materials:

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

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