N-phenylmethoxycarbonyl-S-(2,3,4-tri-O-acetyl-6-O,N-carbonylidene-5-deoxy-1,5-imino-β-D-glucopyranosyl)-L-cysteine methyl ester

Base Information

Chemical Name:N-phenylmethoxycarbonyl-S-(2,3,4-tri-O-acetyl-6-O,N-carbonylidene-5-deoxy-1,5-imino-β-D-glucopyranosyl)-L-cysteine methyl ester
CAS No.:297730-82-6
Molecular Formula:C₂₅H₃₀N₂O₁₂S
Molecular Weight:582.585
Hs Code.:

Synonyms:N-phenylmethoxycarbonyl-S-(2,3,4-tri-O-acetyl-6-O,N-carbonylidene-5-deoxy-1,5-imino-β-D-glucopyranosyl)-L-cysteine methyl ester

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Chemical Property of N-phenylmethoxycarbonyl-S-(2,3,4-tri-O-acetyl-6-O,N-carbonylidene-5-deoxy-1,5-imino-β-D-glucopyranosyl)-L-cysteine methyl ester

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Technology Process of N-phenylmethoxycarbonyl-S-(2,3,4-tri-O-acetyl-6-O,N-carbonylidene-5-deoxy-1,5-imino-β-D-glucopyranosyl)-L-cysteine methyl ester

There total 6 articles about N-phenylmethoxycarbonyl-S-(2,3,4-tri-O-acetyl-6-O,N-carbonylidene-5-deoxy-1,5-imino-β-D-glucopyranosyl)-L-cysteine methyl ester 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: 61.0%

: 53907-28-1
N-benzyloxycarbonyl-L-cysteine methyl ester

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

: 297730-82-6
N-phenylmethoxycarbonyl-S-(2,3,4-tri-O-acetyl-6-O,N-carbonylidene-5-deoxy-1,5-imino-β-D-glucopyranosyl)-L-cysteine methyl ester

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 4h;
DOI:10.1080/07328300008544110

Reference yield:

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

: 297730-82-6
N-phenylmethoxycarbonyl-S-(2,3,4-tri-O-acetyl-6-O,N-carbonylidene-5-deoxy-1,5-imino-β-D-glucopyranosyl)-L-cysteine methyl ester

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: 61 percent / TMSOTf / CH₂Cl₂ / 4 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:

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

: 297730-82-6
N-phenylmethoxycarbonyl-S-(2,3,4-tri-O-acetyl-6-O,N-carbonylidene-5-deoxy-1,5-imino-β-D-glucopyranosyl)-L-cysteine methyl ester

Guidance literature:: Multi-step reaction with 4 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: 61 percent / TMSOTf / CH₂Cl₂ / 4 h / 20 °C

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