phenyl 2,3,4-tri-O-acetyl-6-O,N-carbonylidene-5-deoxy-1,5-imino-1-thio-β-D-glucopyranoside

Base Information

Chemical Name:phenyl 2,3,4-tri-O-acetyl-6-O,N-carbonylidene-5-deoxy-1,5-imino-1-thio-β-D-glucopyranoside
CAS No.:297730-89-3
Molecular Formula:C₁₉H₂₁NO₈S
Molecular Weight:423.444
Hs Code.:

Synonyms:phenyl 2,3,4-tri-O-acetyl-6-O,N-carbonylidene-5-deoxy-1,5-imino-1-thio-β-D-glucopyranoside

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Chemical Property of phenyl 2,3,4-tri-O-acetyl-6-O,N-carbonylidene-5-deoxy-1,5-imino-1-thio-β-D-glucopyranoside

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Technology Process of phenyl 2,3,4-tri-O-acetyl-6-O,N-carbonylidene-5-deoxy-1,5-imino-1-thio-β-D-glucopyranoside

There total 6 articles about phenyl 2,3,4-tri-O-acetyl-6-O,N-carbonylidene-5-deoxy-1,5-imino-1-thio-β-D-glucopyranoside 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: 90.0%

: 108-98-5
thiophenol

: 297730-79-1
2,3,4-tri-O-acetyl-6-O,N-carbonylidene-5-deoxy-1,5-imino-α-D-glucopyranosyl trichloroacetimidate

: 297730-89-3
phenyl 2,3,4-tri-O-acetyl-6-O,N-carbonylidene-5-deoxy-1,5-imino-1-thio-β-D-glucopyranoside

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 3h;
DOI:10.1080/07328300008544110

Reference yield:

: 84036-72-6
5-benzyloxycarbonylamino-5-deoxy-1,2-O-isopropylidene-α-D-gluco-1,4-furanose

: 297730-89-3
phenyl 2,3,4-tri-O-acetyl-6-O,N-carbonylidene-5-deoxy-1,5-imino-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: TFA / dioxane; H₂O / 14 h / 60 °C

2: 1M NaOH; IRA-420 (OH^-) / H₂O

3: 96 percent / pyridine / 20 h / 20 °C

4: 75 percent / N₂H₄*AcOH / dimethylformamide / 3 h / 20 °C

5: 76 percent / DBU / CH₂Cl₂ / 3 h / 20 °C

6: 90 percent / TMSOTf / CH₂Cl₂ / 3 h / 20 °C

With sodium hydroxide; trimethylsilyl trifluoromethanesulfonate; IRA-420 (OH^-); hydrazinium monoacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; In 1,4-dioxane; pyridine; dichloromethane; water; N,N-dimethyl-formamide; 1: de-O-isopropylidenation / 2: Cyclization / 3: Acetylation / 4: Deacetylation / 5: Addition / 6: glycosylation;
DOI:10.1080/07328300008544110

Reference yield:

: 260790-66-7
1,2,3,4-tetra-O-acetyl-6-O,N-carbonylidene-5-deoxy-1,5-imino-α-D-glucopyranose

: 297730-89-3
phenyl 2,3,4-tri-O-acetyl-6-O,N-carbonylidene-5-deoxy-1,5-imino-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 75 percent / N₂H₄*AcOH / dimethylformamide / 3 h / 20 °C

2: 76 percent / DBU / CH₂Cl₂ / 3 h / 20 °C

3: 90 percent / TMSOTf / CH₂Cl₂ / 3 h / 20 °C

With trimethylsilyl trifluoromethanesulfonate; hydrazinium monoacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; N,N-dimethyl-formamide; 1: Deacetylation / 2: Addition / 3: glycosylation;
DOI:10.1080/07328300008544110