thexyldimethylsilyl 2-O-benzoyl-4,6-O-benzylidene-3-S-(6-O,N-carbonylidene-5-deoxy-1,5-imino-β-D-glucopyranosyl)-3-thio-β-D-galactopyranoside

Base Information

Chemical Name:thexyldimethylsilyl 2-O-benzoyl-4,6-O-benzylidene-3-S-(6-O,N-carbonylidene-5-deoxy-1,5-imino-β-D-glucopyranosyl)-3-thio-β-D-galactopyranoside
CAS No.:297730-86-0
Molecular Formula:C₃₅H₄₇NO₁₁SSi
Molecular Weight:717.91
Hs Code.:

thexyldimethylsilyl 2-O-benzoyl-4,6-O-benzylidene-3-S-(6-O,N-carbonylidene-5-deoxy-1,5-imino-β-D-glucopyranosyl)-3-thio-β-D-galactopyranoside

Synonyms:thexyldimethylsilyl 2-O-benzoyl-4,6-O-benzylidene-3-S-(6-O,N-carbonylidene-5-deoxy-1,5-imino-β-D-glucopyranosyl)-3-thio-β-D-galactopyranoside

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Chemical Property of thexyldimethylsilyl 2-O-benzoyl-4,6-O-benzylidene-3-S-(6-O,N-carbonylidene-5-deoxy-1,5-imino-β-D-glucopyranosyl)-3-thio-β-D-galactopyranoside

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Technology Process of thexyldimethylsilyl 2-O-benzoyl-4,6-O-benzylidene-3-S-(6-O,N-carbonylidene-5-deoxy-1,5-imino-β-D-glucopyranosyl)-3-thio-β-D-galactopyranoside

There total 7 articles about thexyldimethylsilyl 2-O-benzoyl-4,6-O-benzylidene-3-S-(6-O,N-carbonylidene-5-deoxy-1,5-imino-β-D-glucopyranosyl)-3-thio-β-D-galactopyranoside 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%

: 297730-85-9
thexyldimethylsilyl 3-S-(2,3,4-tri-O-acetyl-6-O,N-carbonylidene-5-deoxy-1,5-imino-β-D-glucopyranosyl)-2-O-benzoyl-4,6-O-benzylidene-3-thio-β-D-galactopyranoside

: 297730-86-0
thexyldimethylsilyl 2-O-benzoyl-4,6-O-benzylidene-3-S-(6-O,N-carbonylidene-5-deoxy-1,5-imino-β-D-glucopyranosyl)-3-thio-β-D-galactopyranoside

Guidance literature:: With sodium methylate; In methanol; 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

: 297730-86-0
thexyldimethylsilyl 2-O-benzoyl-4,6-O-benzylidene-3-S-(6-O,N-carbonylidene-5-deoxy-1,5-imino-β-D-glucopyranosyl)-3-thio-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 7 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: 71 percent / TMSOTf / CH₂Cl₂ / 1 h / 20 °C

7: 92 percent / NaOMe / methanol / 3 h / 20 °C

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

Reference yield:

: 260790-65-6
(5R,6S,7R,8R,8aR)-5,6,7,8-tetrahydroxy-2-oxa-3-oxoindolizidine

: 297730-86-0
thexyldimethylsilyl 2-O-benzoyl-4,6-O-benzylidene-3-S-(6-O,N-carbonylidene-5-deoxy-1,5-imino-β-D-glucopyranosyl)-3-thio-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 96 percent / pyridine / 20 h / 20 °C

2: 75 percent / N₂H₄*AcOH / dimethylformamide / 3 h / 20 °C

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

4: 71 percent / TMSOTf / CH₂Cl₂ / 1 h / 20 °C

5: 92 percent / NaOMe / methanol / 3 h / 20 °C

With trimethylsilyl trifluoromethanesulfonate; sodium methylate; hydrazinium monoacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; 1: Acetylation / 2: Deacetylation / 3: Addition / 4: glycosylation / 5: Deacetylation;
DOI:10.1080/07328300008544110