phenyl O-(2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-(1->4)-2-O-benzoyl-6-O-benzyl-1-thio-β-D-glucopyranoside 3,6'-malonate

Base Information

Chemical Name:phenyl O-(2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-(1->4)-2-O-benzoyl-6-O-benzyl-1-thio-β-D-glucopyranoside 3,6'-malonate
CAS No.:260780-00-5
Molecular Formula:C₅₆H₅₄O₁₃S
Molecular Weight:967.103
Hs Code.:

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

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

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

There total 6 articles about phenyl O-(2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-(1->4)-2-O-benzoyl-6-O-benzyl-1-thio-β-D-glucopyranoside 3,6'-malonate 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: 69.0%

: 260779-99-5
ethyl 2,3,4-tri-O-benzyl-6-O-[(2-O-benzoyl-6-O-benzyl-1-phenylthio-β-D-glucopyranos-3-yloxy)carbonylethanoyl]-1-thio-α-D-mannopyranoside

: 260780-00-5
phenyl O-(2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-(1->4)-2-O-benzoyl-6-O-benzyl-1-thio-β-D-glucopyranoside 3,6'-malonate

Guidance literature:: With 4 A molecular sieve; methyl trifluoromethanesulfonate; In acetonitrile; at 20 ℃; for 6h;
DOI:10.1002/(SICI)1099-0690(200001)2000:1<181::AID-EJOC181>3.0.CO;2-7

Reference yield:

: 39483-51-7,119645-03-3,126461-54-9,128850-50-0
ethyl 2,3,4-tri-O-benzyl-1-thio-α-D-mannopyranoside

: 260780-00-5
phenyl O-(2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-(1->4)-2-O-benzoyl-6-O-benzyl-1-thio-β-D-glucopyranoside 3,6'-malonate

Guidance literature:: Multi-step reaction with 5 steps

1: 64 percent / DCC; 1-hydroxy-1H-benzotriazole / CH₂Cl₂ / 24 h / 20 °C

2: 100 percent / trifluoroacetic acid / CH₂Cl₂ / 3 h / 20 °C

3: 81 percent / DCC; DMAP / CH₂Cl₂ / 24 h / 20 °C

4: 71 percent / HCl; NaCNBH₃; 3 Angstroem molecular sieves / tetrahydrofuran / 20 °C

5: 69 percent / methyl trifluoromethanesulfonate; 4 Angstroem molecular sieves / acetonitrile / 6 h / 20 °C

With hydrogenchloride; dmap; 3 A molecular sieve; 4 A molecular sieve; sodium cyanoborohydride; benzotriazol-1-ol; dicyclohexyl-carbodiimide; trifluoroacetic acid; methyl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; acetonitrile; 1: Condensation / 2: Elimination / 3: Condensation / 4: Hydrolysis / 5: Elimination;
DOI:10.1002/(SICI)1099-0690(200001)2000:1<181::AID-EJOC181>3.0.CO;2-7

Reference yield:

: 260779-95-1
phenyl 2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside

: 260780-00-5
phenyl O-(2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-(1->4)-2-O-benzoyl-6-O-benzyl-1-thio-β-D-glucopyranoside 3,6'-malonate

Guidance literature:: Multi-step reaction with 3 steps

1: 81 percent / DCC; DMAP / CH₂Cl₂ / 24 h / 20 °C

2: 71 percent / HCl; NaCNBH₃; 3 Angstroem molecular sieves / tetrahydrofuran / 20 °C

3: 69 percent / methyl trifluoromethanesulfonate; 4 Angstroem molecular sieves / acetonitrile / 6 h / 20 °C

With hydrogenchloride; dmap; 3 A molecular sieve; 4 A molecular sieve; sodium cyanoborohydride; dicyclohexyl-carbodiimide; methyl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; acetonitrile; 1: Condensation / 2: Hydrolysis / 3: Elimination;
DOI:10.1002/(SICI)1099-0690(200001)2000:1<181::AID-EJOC181>3.0.CO;2-7