allyl 2-acetamido-4,6-O-benzylidene-3-O-(2-butenyl)-2-deoxy-β-D-glucopyranoside

Base Information

• Chemical Name: allyl 2-acetamido-4,6-O-benzylidene-3-O-(2-butenyl)-2-deoxy-β-D-glucopyranoside
• CAS No.: 78185-03-2
• Molecular Formula: C₂₂H₂₉NO₆
• Molecular Weight: 403.475
• Mol file: 78185-03-2.mol

Synonyms:allyl 2-acetamido-4,6-O-benzylidene-3-O-(2-butenyl)-2-deoxy-β-D-glucopyranoside

Chemical Property of allyl 2-acetamido-4,6-O-benzylidene-3-O-(2-butenyl)-2-deoxy-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl 2-acetamido-4,6-O-benzylidene-3-O-(2-butenyl)-2-deoxy-β-D-glucopyranoside

There total 1 articles about allyl 2-acetamido-4,6-O-benzylidene-3-O-(2-butenyl)-2-deoxy-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%

(E/Z)-crotyl bromide (4784-77-4,29576-14-5,39616-19-8) + allyl 2-deoxy-2-acetamido-4,6-O-benzylidene-β-D-glucopyranoside (65947-37-7) → allyl 2-acetamido-4,6-O-benzylidene-3-O-(2-butenyl)-2-deoxy-β-D-glucopyranoside (78185-03-2)

Guidance literature:

With barium hydroxide octahydrate; barium(II) oxide; In N,N-dimethyl-formamide; for 0.5h; Ambient temperature;

DOI:10.1016/S0008-6215(00)85253-2

Reference yield:

allyl 2-acetamido-4,6-O-benzylidene-3-O-(2-butenyl)-2-deoxy-β-D-glucopyranoside (78185-03-2) → benzyl 2-acetamido-4-O-<2-acetamido-4-O-acetyl-6-O-benzyl-3-O-(2-butenyl)-2-deoxy-β-D-glucopyranosyl>-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (78138-60-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 93 percent / 60 percent acetic acid / 2 h / 80 °C

2: 33 percent / barium oxide, barium hydroxide octahydrate / dimethylformamide / Ambient temperature

3: 15.3 g / pyridine / 3.5 h / 0 °C

4: 61 percent / 1,4-diazabicyclo<2.2.2>octane / chlorotris(triphenylphosphine)rhodium (I) / ethanol; toluene; H₂O / 2 h / Heating

5: 50 percent / mercuric chloride, mercuric oxide / acetonitrile / 5 h / Ambient temperature

6: 31.2 percent / p-toluenesulfonic acid / 1,2-dichloro-ethane / 1.) 3 h, 75 deg C; 2.) 75 deg C, 9 h

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; barium hydroxide octahydrate; toluene-4-sulfonic acid; acetic acid; mercury dichloride; mercury(II) oxide; barium(II) oxide; Wilkinson's catalyst; In ethanol; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/S0008-6215(00)85253-2

Reference yield:

allyl 2-acetamido-4,6-O-benzylidene-3-O-(2-butenyl)-2-deoxy-β-D-glucopyranoside (78185-03-2) → 2-methyl-<2-acetamido-4-O-acetyl-6-O-benzyl-3-O-(2-butenyl)-1,2-dideoxy-α-D-glucopyrano>-<2,1-d>-2-oxazoline (78138-59-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 93 percent / 60 percent acetic acid / 2 h / 80 °C

2: 33 percent / barium oxide, barium hydroxide octahydrate / dimethylformamide / Ambient temperature

3: 15.3 g / pyridine / 3.5 h / 0 °C

4: 61 percent / 1,4-diazabicyclo<2.2.2>octane / chlorotris(triphenylphosphine)rhodium (I) / ethanol; toluene; H₂O / 2 h / Heating

5: 50 percent / mercuric chloride, mercuric oxide / acetonitrile / 5 h / Ambient temperature

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; barium hydroxide octahydrate; acetic acid; mercury dichloride; mercury(II) oxide; barium(II) oxide; Wilkinson's catalyst; In ethanol; water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/S0008-6215(00)85253-2

upstream raw materials:

(E/Z)-crotyl bromide

allyl 2-deoxy-2-acetamido-4,6-O-benzylidene-β-D-glucopyranoside

Downstream raw materials:

allyl 2-acetamido-4-O-benzyl-3-O-(2-butenyl)-2-deoxy-β-D-glucopyranoside

allyl 2-acetamido-6-O-benzyl-3-O-(2-butenyl)-2-deoxy-β-D-glucopyranoside

2-methyl-<2-acetamido-4-O-acetyl-6-O-benzyl-3-O-(2-butenyl)-1,2-dideoxy-α-D-glucopyrano>-<2,1-d>-2-oxazoline

allyl 2-acetamido-4-O-acetyl-6-O-benzyl-3-O-(2-butenyl)-2-deoxy-β-D-glucopyranoside