phenyl 3,4-di-O-benzyl-2,6-di-O-levulinoyl-α-D-mannopyranosyl-(1→6)-2,3,4-tri-O-benzoyl-1-thio-α-D-mannopyranoside

Base Information

Chemical Name:phenyl 3,4-di-O-benzyl-2,6-di-O-levulinoyl-α-D-mannopyranosyl-(1→6)-2,3,4-tri-O-benzoyl-1-thio-α-D-mannopyranoside
CAS No.:1439439-53-8
Molecular Formula:C₆₃H₆₂O₁₇S
Molecular Weight:1123.24
Hs Code.:

Synonyms:phenyl 3,4-di-O-benzyl-2,6-di-O-levulinoyl-α-D-mannopyranosyl-(1→6)-2,3,4-tri-O-benzoyl-1-thio-α-D-mannopyranoside

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Chemical Property of phenyl 3,4-di-O-benzyl-2,6-di-O-levulinoyl-α-D-mannopyranosyl-(1→6)-2,3,4-tri-O-benzoyl-1-thio-α-D-mannopyranoside

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Technology Process of phenyl 3,4-di-O-benzyl-2,6-di-O-levulinoyl-α-D-mannopyranosyl-(1→6)-2,3,4-tri-O-benzoyl-1-thio-α-D-mannopyranoside

There total 6 articles about phenyl 3,4-di-O-benzyl-2,6-di-O-levulinoyl-α-D-mannopyranosyl-(1→6)-2,3,4-tri-O-benzoyl-1-thio-α-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: 89.0%

: 1439439-52-7
3,4-di-O-benzyl-2,6-di-O-levulinoyl-α-D-mannopyranosyltrichloroacetimidate

: 150935-65-2
phenyl 2,3,4-tri-O-benzoyl-1-thio-α-D-mannopyranoside

: 1439439-53-8
phenyl 3,4-di-O-benzyl-2,6-di-O-levulinoyl-α-D-mannopyranosyl-(1→6)-2,3,4-tri-O-benzoyl-1-thio-α-D-mannopyranoside

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -80 - 0 ℃; for 2.5h; regioselective reaction; Molecular sieve;
DOI:10.1039/c3ob40421h

Reference yield:

: 1439439-50-5
p-methoxyphenyl 2,6-di-O-acetyl-3,4-di-O-benzyl-α-D-mannopyranoside

: 1439439-53-8
phenyl 3,4-di-O-benzyl-2,6-di-O-levulinoyl-α-D-mannopyranosyl-(1→6)-2,3,4-tri-O-benzoyl-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: sodium methylate; methanol / methanol; dichloromethane / 1 h / 20 °C

2: dicyclohexyl-carbodiimide / dichloromethane / 4 h / 20 °C

3: water; ammonium cerium (IV) nitrate / acetonitrile / 0.67 h / 0 °C

4: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / 20 °C

5: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2.5 h / -80 - 0 °C / Molecular sieve

With methanol; ammonium cerium (IV) nitrate; trimethylsilyl trifluoromethanesulfonate; water; sodium methylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; dicyclohexyl-carbodiimide; In methanol; dichloromethane; acetonitrile;
DOI:10.1039/c3ob40421h

Reference yield:

: 1439439-51-6
p-methoxyphenyl 2,6-di-O-levulinoyl-3,4-di-O-benzyl-α-D-mannopyranoside

: 1439439-53-8
phenyl 3,4-di-O-benzyl-2,6-di-O-levulinoyl-α-D-mannopyranosyl-(1→6)-2,3,4-tri-O-benzoyl-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: water; ammonium cerium (IV) nitrate / acetonitrile / 0.67 h / 0 °C

2: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / 20 °C

3: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2.5 h / -80 - 0 °C / Molecular sieve

With ammonium cerium (IV) nitrate; trimethylsilyl trifluoromethanesulfonate; water; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; acetonitrile;
DOI:10.1039/c3ob40421h