benzyl 2-acetamido-4-O-<2-acetamido-6-O-benzyl-3-O-(2-butenyl)-2-deoxy-β-D-glucopyranosyl>-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

Base Information

• Chemical Name: benzyl 2-acetamido-4-O-<2-acetamido-6-O-benzyl-3-O-(2-butenyl)-2-deoxy-β-D-glucopyranosyl>-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside
• CAS No.: 78138-61-1
• Molecular Formula: C₄₈H₅₈N₂O₁₁
• Molecular Weight: 838.995
• Mol file: 78138-61-1.mol

Synonyms:benzyl 2-acetamido-4-O-<2-acetamido-6-O-benzyl-3-O-(2-butenyl)-2-deoxy-β-D-glucopyranosyl>-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

Chemical Property of benzyl 2-acetamido-4-O-<2-acetamido-6-O-benzyl-3-O-(2-butenyl)-2-deoxy-β-D-glucopyranosyl>-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 2-acetamido-4-O-<2-acetamido-6-O-benzyl-3-O-(2-butenyl)-2-deoxy-β-D-glucopyranosyl>-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

There total 8 articles about benzyl 2-acetamido-4-O-<2-acetamido-6-O-benzyl-3-O-(2-butenyl)-2-deoxy-β-D-glucopyranosyl>-3,6-di-O-benzyl-2-deoxy-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: 93.0%

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) → benzyl 2-acetamido-4-O-<2-acetamido-6-O-benzyl-3-O-(2-butenyl)-2-deoxy-β-D-glucopyranosyl>-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (78138-61-1)

Guidance literature:

With sodium methylate; In methanol; Ambient temperature;

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

Reference yield:

allyl 2-deoxy-2-acetamido-4,6-O-benzylidene-β-D-glucopyranoside (65947-37-7) → benzyl 2-acetamido-4-O-<2-acetamido-6-O-benzyl-3-O-(2-butenyl)-2-deoxy-β-D-glucopyranosyl>-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (78138-61-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 90 percent / barium oxide, barium hydroxide octahydrate / dimethylformamide / 0.5 h / Ambient temperature

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

3: 33 percent / barium oxide, barium hydroxide octahydrate / dimethylformamide / Ambient temperature

4: 15.3 g / pyridine / 3.5 h / 0 °C

5: 61 percent / 1,4-diazabicyclo<2.2.2>octane / chlorotris(triphenylphosphine)rhodium (I) / ethanol; toluene; H₂O / 2 h / Heating

6: 50 percent / mercuric chloride, mercuric oxide / acetonitrile / 5 h / Ambient temperature

7: 31.2 percent / p-toluenesulfonic acid / 1,2-dichloro-ethane / 1.) 3 h, 75 deg C; 2.) 75 deg C, 9 h

8: 93 percent / NaOMe / methanol / Ambient temperature

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; barium hydroxide octahydrate; sodium methylate; toluene-4-sulfonic acid; acetic acid; mercury dichloride; mercury(II) oxide; barium(II) oxide; Wilkinson's catalyst; In methanol; 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-6-O-benzyl-3-O-(2-butenyl)-2-deoxy-β-D-glucopyranoside (78138-55-3) → benzyl 2-acetamido-4-O-<2-acetamido-6-O-benzyl-3-O-(2-butenyl)-2-deoxy-β-D-glucopyranosyl>-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (78138-61-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 15.3 g / pyridine / 3.5 h / 0 °C

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

3: 50 percent / mercuric chloride, mercuric oxide / acetonitrile / 5 h / Ambient temperature

4: 31.2 percent / p-toluenesulfonic acid / 1,2-dichloro-ethane / 1.) 3 h, 75 deg C; 2.) 75 deg C, 9 h

5: 93 percent / NaOMe / methanol / Ambient temperature

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; sodium methylate; toluene-4-sulfonic acid; mercury dichloride; mercury(II) oxide; Wilkinson's catalyst; In methanol; ethanol; water; 1,2-dichloro-ethane; toluene; acetonitrile;

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

upstream raw materials:

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

allyl 2-deoxy-2-acetamido-4,6-O-benzylidene-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