2,4-di-O-benzyl-6-deoxy-6-thiophenyl-β-D-mannopyranosyl-(1->2)-(methyl 3,4-di-O-benzyl-6-deoxy-α-D-mannopyranoside)

Base Information

Chemical Name:2,4-di-O-benzyl-6-deoxy-6-thiophenyl-β-D-mannopyranosyl-(1->2)-(methyl 3,4-di-O-benzyl-6-deoxy-α-D-mannopyranoside)
CAS No.:1361383-34-7
Molecular Formula:C₄₇H₅₂O₉S
Molecular Weight:792.99
Hs Code.:

Synonyms:2,4-di-O-benzyl-6-deoxy-6-thiophenyl-β-D-mannopyranosyl-(1->2)-(methyl 3,4-di-O-benzyl-6-deoxy-α-D-mannopyranoside)

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Chemical Property of 2,4-di-O-benzyl-6-deoxy-6-thiophenyl-β-D-mannopyranosyl-(1->2)-(methyl 3,4-di-O-benzyl-6-deoxy-α-D-mannopyranoside)

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Technology Process of 2,4-di-O-benzyl-6-deoxy-6-thiophenyl-β-D-mannopyranosyl-(1->2)-(methyl 3,4-di-O-benzyl-6-deoxy-α-D-mannopyranoside)

There total 12 articles about 2,4-di-O-benzyl-6-deoxy-6-thiophenyl-β-D-mannopyranosyl-(1->2)-(methyl 3,4-di-O-benzyl-6-deoxy-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: 60.0%

: 1361383-33-6
2,4-di-O-benzyl-6-deoxy-3-(2-naphthylmethyl)-6-thiophenyl-β-D-mannopyranosyl-(1->2)-(methyl 3,4-di-O-benzyl-6-deoxy-α-D-mannopyranoside)

: 1361383-34-7
2,4-di-O-benzyl-6-deoxy-6-thiophenyl-β-D-mannopyranosyl-(1->2)-(methyl 3,4-di-O-benzyl-6-deoxy-α-D-mannopyranoside)

Guidance literature:: With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; for 1h;
DOI:10.1039/c2cc17623h

Reference yield:

: C₃₃H₅₄O₆Si₂

: 1361383-34-7
2,4-di-O-benzyl-6-deoxy-6-thiophenyl-β-D-mannopyranosyl-(1->2)-(methyl 3,4-di-O-benzyl-6-deoxy-α-D-mannopyranoside)

Guidance literature:: Multi-step reaction with 9 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h

2: 1H-imidazole; iodine; triphenylphosphine / toluene / 3 h / 70 °C / Inert atmosphere

3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 20 °C

4: sodium hydride / N,N-dimethyl-formamide; mineral oil

5: sulfuric acid / 7 h / 0 °C

6: piperidine / tetrahydrofuran

7: caesium carbonate / water; acetone / 20 °C

8: trifluorormethanesulfonic acid / dichloromethane / 96 h / -80 °C / Molecular sieve

9: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h

With piperidine; 1H-imidazole; trifluorormethanesulfonic acid; sulfuric acid; tetrabutyl ammonium fluoride; water; iodine; sodium hydride; caesium carbonate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; mineral oil;
DOI:10.1039/c2cc17623h

Reference yield:

: 906641-09-6
(2S,3S,4R,5S,6S)-4,5-Bis-benzyloxy-6-iodomethyl-2-methoxy-tetrahydro-pyran-3-ol

: 1361383-34-7
2,4-di-O-benzyl-6-deoxy-6-thiophenyl-β-D-mannopyranosyl-(1->2)-(methyl 3,4-di-O-benzyl-6-deoxy-α-D-mannopyranoside)

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium tetrahydroborate / dimethyl sulfoxide / 100 °C

1.2: 0.25 h / 100 °C

2.1: trifluorormethanesulfonic acid / dichloromethane / 96 h / -80 °C / Molecular sieve

3.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h

With sodium tetrahydroborate; trifluorormethanesulfonic acid; water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; dimethyl sulfoxide;
DOI:10.1039/c2cc17623h