phenyl 2,3,6-tri-O-benzyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzoyl-1-thio-β-D-xylopyranoside

Base Information

Chemical Name:phenyl 2,3,6-tri-O-benzyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzoyl-1-thio-β-D-xylopyranoside
CAS No.:1338548-70-1
Molecular Formula:C₅₂H₅₀O₁₁S
Molecular Weight:883.028
Hs Code.:

Synonyms:phenyl 2,3,6-tri-O-benzyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzoyl-1-thio-β-D-xylopyranoside

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Chemical Property of phenyl 2,3,6-tri-O-benzyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzoyl-1-thio-β-D-xylopyranoside

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Technology Process of phenyl 2,3,6-tri-O-benzyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzoyl-1-thio-β-D-xylopyranoside

There total 4 articles about phenyl 2,3,6-tri-O-benzyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzoyl-1-thio-β-D-xylopyranoside 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%

: 1338548-68-7
phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzoyl-1-thio-β-D-xylopyranoside

: 1338548-70-1
phenyl 2,3,6-tri-O-benzyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzoyl-1-thio-β-D-xylopyranoside

Guidance literature:: phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzoyl-1-thio-β-D-xylopyranoside; With sodium cyanoborohydride; In tetrahydrofuran; at 0 ℃; for 1h; Molecular sieve;

With hydrogenchloride; In tetrahydrofuran; diethyl ether;
DOI:10.1021/jo201780e

Reference yield:

: 159407-17-7
phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

: 1338548-70-1
phenyl 2,3,6-tri-O-benzyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzoyl-1-thio-β-D-xylopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 2,4,6-tri-tert-butylpyrimidine / dichloromethane / 0.5 h / -65 - -60 °C / Molecular sieve; Inert atmosphere

1.2: 0.08 h / -78 °C / Molecular sieve; Inert atmosphere

1.3: 2.5 h / -60 °C / Molecular sieve; Inert atmosphere

2.1: acetic acid / 3 h / 65 °C

2.2: 2 h / 0 °C

3.1: sodium cyanoborohydride / tetrahydrofuran / 1 h / 0 °C / Molecular sieve

With 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; sodium cyanoborohydride; acetic acid; 2,4,6-tri-tert-butylpyrimidine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo201780e

Reference yield:

: 521304-46-1
phenyl 2,3-O-isopropylidene-1-thio-β-D-xylopyranoside

: 1338548-70-1
phenyl 2,3,6-tri-O-benzyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzoyl-1-thio-β-D-xylopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 2,4,6-tri-tert-butylpyrimidine / dichloromethane / 0.5 h / -65 - -60 °C / Molecular sieve; Inert atmosphere

1.2: 0.08 h / -78 °C / Molecular sieve; Inert atmosphere

1.3: 2.5 h / -60 °C / Molecular sieve; Inert atmosphere

2.1: acetic acid / 3 h / 65 °C

2.2: 2 h / 0 °C

3.1: sodium cyanoborohydride / tetrahydrofuran / 1 h / 0 °C / Molecular sieve

With 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; sodium cyanoborohydride; acetic acid; 2,4,6-tri-tert-butylpyrimidine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo201780e