benzyl 2-acetamido-3-O-(2-butenyl)-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside

Base Information

Chemical Name:benzyl 2-acetamido-3-O-(2-butenyl)-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside
CAS No.:83100-63-4
Molecular Formula:C₂₂H₃₁NO₆
Molecular Weight:405.491
Hs Code.:

Synonyms:benzyl 2-acetamido-3-O-(2-butenyl)-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside

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Chemical Property of benzyl 2-acetamido-3-O-(2-butenyl)-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside

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Technology Process of benzyl 2-acetamido-3-O-(2-butenyl)-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside

There total 1 articles about benzyl 2-acetamido-3-O-(2-butenyl)-2-deoxy-4,6-O-isopropylidene-α-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: 76.4%

: 4784-77-4,29576-14-5,39616-19-8
(E/Z)-crotyl bromide

: 66026-10-6
N-((4aR,6S,7R,8R,8aS)-6-(benzyloxy)-8-hydroxy-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-7-yl)acetamide

: 83100-63-4
benzyl 2-acetamido-3-O-(2-butenyl)-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside

Guidance literature:: With barium hydroxide octahydrate; barium(II) oxide; In N,N-dimethyl-formamide; at 0 - 22 ℃; for 36h;
DOI:10.1016/S0008-6215(00)82587-2

Reference yield: 96.4%

: 83100-63-4
benzyl 2-acetamido-3-O-(2-butenyl)-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside

: 83100-64-5
N-{(2S,3R,4R,5S,6R)-2-Benzyloxy-4-[((E)-but-2-enyl)oxy]-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide

Guidance literature:: With acetic acid; In water; at 60 ℃; for 3h;
DOI:10.1016/S0008-6215(00)82587-2

Reference yield:

: 83100-63-4
benzyl 2-acetamido-3-O-(2-butenyl)-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside

: C₅₅H₆₉N₅O₁₆

Guidance literature:: Multi-step reaction with 12 steps

1: 96.4 percent / 60percent acetic acid / H₂O / 3 h / 60 °C

2: 82 percent / pyridine / 1 h / -20 °C

3: p-TsOH*H₂O / dioxane / 3 h / Ambient temperature

4: 1.) barium oxide, barium hydroxide octahydrate; 2.) 70percent acetic acid / 1.) N,N-dimethylformamide, 0 deg C, room temperature, 18 h; 2.) water, 50 deg C, 4 h

5: 36.1 percent / p-TsOH / 1,2-dichloro-ethane / 10 h / Heating

6: 467 mg / sodium methoxide / methanol

7: 384 mg / p-TsOH*H₂O / dimethylformamide / 2 h / 50 °C

8: 1.) barium oxide, barium hydroxide octahydrate; 2.) 70percent acetic acid / 1.) N,N-dimethylformamide, room temperature, 18 h; 2.) water, 50 deg C, 4 h

9: 76.2 percent / potassium tert-butoxide / dimethylsulfoxide / 4 h / 50 °C

10: 1.) sodium hydride / 1.) 1,4-dioxane, 95 deg C, 1.5 h; 2.) 1,4-dioxane, 65 deg C, 3 h

11: 1.) N-hydroxylsuccinimide, dicyclohexylcarbodiimide; 2.) triethylamine / 1.) 1,4-dioxane, room temperature, 2.5 h; 2.) 1,4-dioxane, room temperature, 2 h

12: 100 percent / 60percent acetic acid / H₂O / 1 h / 50 °C

With pyridine; 1-hydroxy-pyrrolidine-2,5-dione; barium hydroxide octahydrate; potassium tert-butylate; sodium methylate; sodium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; dicyclohexyl-carbodiimide; barium(II) oxide; In 1,4-dioxane; methanol; water; dimethyl sulfoxide; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(00)82587-2