ethyl 2,6-dideoxy-3-O-(p-methoxybenzoyl)-4-O-(p-nitrobenzoyl)-1-thio-β-D-ribo-hexopyranoside

Base Information

Chemical Name:ethyl 2,6-dideoxy-3-O-(p-methoxybenzoyl)-4-O-(p-nitrobenzoyl)-1-thio-β-D-ribo-hexopyranoside
CAS No.:98292-29-6
Molecular Formula:C₂₃H₂₅NO₈S
Molecular Weight:475.519
Hs Code.:

Synonyms:ethyl 2,6-dideoxy-3-O-(p-methoxybenzoyl)-4-O-(p-nitrobenzoyl)-1-thio-β-D-ribo-hexopyranoside

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Chemical Property of ethyl 2,6-dideoxy-3-O-(p-methoxybenzoyl)-4-O-(p-nitrobenzoyl)-1-thio-β-D-ribo-hexopyranoside

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Technology Process of ethyl 2,6-dideoxy-3-O-(p-methoxybenzoyl)-4-O-(p-nitrobenzoyl)-1-thio-β-D-ribo-hexopyranoside

There total 10 articles about ethyl 2,6-dideoxy-3-O-(p-methoxybenzoyl)-4-O-(p-nitrobenzoyl)-1-thio-β-D-ribo-hexopyranoside 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:

: 83497-33-0
methyl 4-O-benzoyl-6-bromo-2,6-dideoxy-α-D-ribo-hexopyranoside

: 98292-29-6
ethyl 2,6-dideoxy-3-O-(p-methoxybenzoyl)-4-O-(p-nitrobenzoyl)-1-thio-β-D-ribo-hexopyranoside

Guidance literature:: Multi-step reaction with 9 steps

1: pyridinium p-toluenesulfonate / CH₂Cl₂ / 9 h / Ambient temperature

2: 31 g / aq. KOH / methanol / 0.42 h / Ambient temperature

3: 19.5 percent / LiAlH₄ / tetrahydrofuran / 2 h / Heating

4: NaH, 18-crown-6 / dioxane / 1 h / Heating

5: 53.6 percent / 4-(dimethylamino)pyridine / pyridine / 5 h / 60 °C

6: 96 percent / H₂ / Pd/C / ethanol / 5 h

7: 90 percent / 4-(dimethylamino)pyridine / pyridine / 4 h / 60 °C

8: 5.8 g / H₂O / acetic acid / 2 h / Heating

9: TsOH / CH₂Cl₂ / 24 h / Ambient temperature

With dmap; potassium hydroxide; lithium aluminium tetrahydride; 18-crown-6 ether; water; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; toluene-4-sulfonic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; ethanol; dichloromethane; acetic acid;
DOI:10.1002/hlca.19850680203

Reference yield:

: 100-07-2
4-methoxy-benzoyl chloride

: 98292-29-6
ethyl 2,6-dideoxy-3-O-(p-methoxybenzoyl)-4-O-(p-nitrobenzoyl)-1-thio-β-D-ribo-hexopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 53.6 percent / 4-(dimethylamino)pyridine / pyridine / 5 h / 60 °C

2: 96 percent / H₂ / Pd/C / ethanol / 5 h

3: 90 percent / 4-(dimethylamino)pyridine / pyridine / 4 h / 60 °C

4: 5.8 g / H₂O / acetic acid / 2 h / Heating

5: TsOH / CH₂Cl₂ / 24 h / Ambient temperature

With dmap; water; hydrogen; toluene-4-sulfonic acid; palladium on activated charcoal; In pyridine; ethanol; dichloromethane; acetic acid;
DOI:10.1002/hlca.19850680203

Reference yield:

: methyl 2,6-dideoxy-3-O-(tetrahydro-2H-2-pyranyl)-D-ribo-hexopyranoside

: 98292-29-6
ethyl 2,6-dideoxy-3-O-(p-methoxybenzoyl)-4-O-(p-nitrobenzoyl)-1-thio-β-D-ribo-hexopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: NaH, 18-crown-6 / dioxane / 1 h / Heating

2: 53.6 percent / 4-(dimethylamino)pyridine / pyridine / 5 h / 60 °C

3: 96 percent / H₂ / Pd/C / ethanol / 5 h

4: 90 percent / 4-(dimethylamino)pyridine / pyridine / 4 h / 60 °C

5: 5.8 g / H₂O / acetic acid / 2 h / Heating

6: TsOH / CH₂Cl₂ / 24 h / Ambient temperature

With dmap; 18-crown-6 ether; water; hydrogen; sodium hydride; toluene-4-sulfonic acid; palladium on activated charcoal; In 1,4-dioxane; pyridine; ethanol; dichloromethane; acetic acid;
DOI:10.1002/hlca.19850680203