methyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

Base Information

• Chemical Name: methyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
• CAS No.: 142560-73-4
• Molecular Formula: C₂₃H₂₇NO₆
• Molecular Weight: 413.47
• Mol file: 142560-73-4.mol

Synonyms:methyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

Chemical Property of methyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

There total 1 articles about methyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-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: 82.0%

benzyl bromide (100-39-0) + methyl 2-acetylamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside (87038-18-4) → methyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside (142560-73-4)

Guidance literature:

With barium dihydroxide; barium(II) oxide; In N,N-dimethyl-formamide; for 2h;

Reference yield: 96.0%

methyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside (142560-73-4) → methyl 2-acetamido-3-O-benzyl-2-deoxy-β-D-glucopyranoside (69892-45-1)

Guidance literature:

With acetic acid; at 80 ℃; for 0.25h;

Reference yield:

methyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside (142560-73-4) → N-[(2R,3R,4S,5S,6S)-4-Hydroxy-6-hydroxymethyl-2-methoxy-5-((1R,2S,3S,4S,5R)-2,3,4-trihydroxy-5-hydroxymethyl-cyclohexylamino)-tetrahydro-pyran-3-yl]-acetamide

Guidance literature:

Multi-step reaction with 11 steps

1: 74 percent / NaCNBH₃ / tetrahydrofuran / 1 h / Ambient temperature

2: Ac₂O, DMSO / 20 h / Ambient temperature

3: 49 percent / L-selectride / tetrahydrofuran / 7 h / refrigeration

4: pyridine / 0.5 h / Ambient temperature

5: NaN₃ / dimethylformamide; H₂O / 32 h / 100 °C

6: 81 percent / hydrogen / 10percent Pd/C / ethanol / 8.5 h / Ambient temperature

7: 2) pyridine / 1) isopropanol, 120 deg C, 15 d

8: 80percent aq. AcOH / 0.5 h / 80 °C

9: hydrogen, HCl / 10percent Pd/C / methanol / 0.5 h / Ambient temperature

10: pyridine

11: 90 percent / NaOMe, MeOH

With pyridine; hydrogenchloride; methanol; sodium azide; hydrogen; sodium methylate; acetic anhydride; L-Selectride; sodium cyanoborohydride; acetic acid; dimethyl sulfoxide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; water; N,N-dimethyl-formamide;

DOI:10.1002/(SICI)1099-0690(199806)1998:6<1099::AID-EJOC1099<3.0.CO;2-R

upstream raw materials:

benzyl bromide

methyl 2-acetylamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

Downstream raw materials:

methyl 2-acetamido-3-O-benzyl-2-deoxy-β-D-glucopyranoside

methyl 2-acetamido-3,6-di-O-benzyl-β-D-glucopyranoside

Acetic acid (3aS,4S,5R,7R,7aS)-5-((2S,3S,4S,5R,6R)-4-acetoxy-2-acetoxymethyl-5-acetylamino-6-methoxy-tetrahydro-pyran-3-ylamino)-7-benzyloxymethyl-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl ester

Acetic acid (2S,3S,4S,5R,6R)-2-acetoxymethyl-5-acetylamino-6-methoxy-3-((1R,2S,3S,4S,5R)-2,3,4-triacetoxy-5-acetoxymethyl-cyclohexylamino)-tetrahydro-pyran-4-yl ester