phenyl 2,3,4-tri-O-benzyl-6-O-(3,4,6-tri-O-benzyl-α-D-lyxo-hexapyranosyl)-β-D-thioglucopyranoside

Base Information

Chemical Name:phenyl 2,3,4-tri-O-benzyl-6-O-(3,4,6-tri-O-benzyl-α-D-lyxo-hexapyranosyl)-β-D-thioglucopyranoside
CAS No.:1401954-91-3
Molecular Formula:C₆₀H₆₂O₉S
Molecular Weight:959.213
Hs Code.:

Synonyms:phenyl 2,3,4-tri-O-benzyl-6-O-(3,4,6-tri-O-benzyl-α-D-lyxo-hexapyranosyl)-β-D-thioglucopyranoside

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Chemical Property of phenyl 2,3,4-tri-O-benzyl-6-O-(3,4,6-tri-O-benzyl-α-D-lyxo-hexapyranosyl)-β-D-thioglucopyranoside

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Technology Process of phenyl 2,3,4-tri-O-benzyl-6-O-(3,4,6-tri-O-benzyl-α-D-lyxo-hexapyranosyl)-β-D-thioglucopyranoside

There total 5 articles about phenyl 2,3,4-tri-O-benzyl-6-O-(3,4,6-tri-O-benzyl-α-D-lyxo-hexapyranosyl)-β-D-thioglucopyranoside 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: 92.0%

: 80040-79-5
3,4,6-tri-O-benzyl-D-galactal

: 87470-73-3,120403-26-1,38184-12-2
phenyl 2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside

: 1401954-91-3
phenyl 2,3,4-tri-O-benzyl-6-O-(3,4,6-tri-O-benzyl-α-D-lyxo-hexapyranosyl)-β-D-thioglucopyranoside

Guidance literature:: With 1,3-bis(3,5-bis(trifluoro-ethyl)phenyl)thiourea; In dichloromethane; for 24h; diastereoselective reaction; Inert atmosphere; Reflux;
DOI:10.1002/anie.201204505

Reference yield:

: 83-87-4,604-68-2,604-69-3,2152-77-4,4026-35-1,4163-59-1,4163-60-4,4163-61-5,4163-65-9,4257-94-7,4257-96-9,16299-15-3,19186-39-1,19189-55-0,25878-60-8,25941-03-1,32445-48-0,32445-49-1,32445-53-7,32445-54-8,34685-58-0,34685-59-1,43168-42-9,43168-44-1,43169-22-8,43169-25-1,66966-07-2,70749-17-6,80184-01-6,93221-01-3,93221-02-4,99630-88-3,109215-53-4,115792-70-6,115792-73-9,139894-92-1,139973-25-4,144071-49-8,147648-81-5
D-glucose pentaacetate

: 1401954-91-3
phenyl 2,3,4-tri-O-benzyl-6-O-(3,4,6-tri-O-benzyl-α-D-lyxo-hexapyranosyl)-β-D-thioglucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: zinc(II) iodide / dichloromethane / 18 h / 20 °C / Inert atmosphere

2.1: triethylamine; water / methanol / 18 h

3.1: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere

4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C / Inert atmosphere

4.2: 0 - 20 °C / Inert atmosphere

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C

6.1: 1,3-bis(3,5-bis(trifluoro-ethyl)phenyl)thiourea / dichloromethane / 24 h / Inert atmosphere; Reflux

With 1H-imidazole; 1,3-bis(3,5-bis(trifluoro-ethyl)phenyl)thiourea; tetrabutyl ammonium fluoride; water; sodium hydride; triethylamine; zinc(II) iodide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; mineral oil;
DOI:10.1002/anie.201204505

Reference yield:

: 4551-15-9
phenylthiotrimethylsilane

: 1401954-91-3
phenyl 2,3,4-tri-O-benzyl-6-O-(3,4,6-tri-O-benzyl-α-D-lyxo-hexapyranosyl)-β-D-thioglucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: zinc(II) iodide / dichloromethane / 18 h / 20 °C / Inert atmosphere

2.1: triethylamine; water / methanol / 18 h

3.1: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere

4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C / Inert atmosphere

4.2: 0 - 20 °C / Inert atmosphere

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C

6.1: 1,3-bis(3,5-bis(trifluoro-ethyl)phenyl)thiourea / dichloromethane / 24 h / Inert atmosphere; Reflux

With 1H-imidazole; 1,3-bis(3,5-bis(trifluoro-ethyl)phenyl)thiourea; tetrabutyl ammonium fluoride; water; sodium hydride; triethylamine; zinc(II) iodide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; mineral oil;
DOI:10.1002/anie.201204505