methyl 3-acetamido-4,6-O-benzylidene-2,3-dideoxy-3-C-methyl-α-D-ribo-hexopyranoside

Base Information

• Chemical Name: methyl 3-acetamido-4,6-O-benzylidene-2,3-dideoxy-3-C-methyl-α-D-ribo-hexopyranoside
• CAS No.: 98758-30-6
• Molecular Formula: C₁₇H₂₃NO₅
• Molecular Weight: 321.373
• Mol file: 98758-30-6.mol

Synonyms:methyl 3-acetamido-4,6-O-benzylidene-2,3-dideoxy-3-C-methyl-α-D-ribo-hexopyranoside

Chemical Property of methyl 3-acetamido-4,6-O-benzylidene-2,3-dideoxy-3-C-methyl-α-D-ribo-hexopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3-acetamido-4,6-O-benzylidene-2,3-dideoxy-3-C-methyl-α-D-ribo-hexopyranoside

There total 12 articles about methyl 3-acetamido-4,6-O-benzylidene-2,3-dideoxy-3-C-methyl-α-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: 41.0%

1-O-Methyl-3-amino-3-C-methyl-4,6-O-benzyliden-2,3-didesoxy-α-D-arabino-hexopyranose (65827-66-9) + acetic anhydride (108-24-7) → methyl 3-acetamido-4,6-O-benzylidene-2,3-dideoxy-3-C-methyl-α-D-arabino-hexopyranoside (65827-67-0,71695-37-9,72244-37-2,98758-30-6)

Guidance literature:

In pyridine; for 12h; Ambient temperature;

Reference yield:

methyl 3-C-(azidomethyl)-4,6-O-benzylidene-2-deoxy-3-O-methylsulphonyl-α-D-arabino-hexopyranoside (98758-27-1) → methyl 3-acetamido-4,6-O-benzylidene-2,3-dideoxy-3-C-methyl-α-D-ribo-hexopyranoside (98758-30-6)

Guidance literature:

With hydrogen; platinum(IV) oxide; In methanol; Ambient temperature;

DOI:10.1016/0008-6215(83)88232-9

Reference yield:

methyl 4,6-O-(R)-benzylidene-2-deoxy-α-D-erythrohexopyranosid-3-ulose (63598-31-2) → methyl 3-acetamido-4,6-O-benzylidene-2,3-dideoxy-3-C-methyl-α-D-ribo-hexopyranoside (98758-30-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 82 percent / ethanol / 2 h / Ambient temperature

2: 1) CeCl₃ / 1) THF, -78 deg C, 1 h, 2) THF, a) -78 deg C, 2 h, b) 0 deg C, 1 h

3: H₂ / 10percent Pd-C / methanol / 20 h / Ambient temperature

4: pyridine / CH₂Cl₂ / 2 h / Ambient temperature

With pyridine; cerium(III) chloride; hydrogen; palladium on activated charcoal; In methanol; ethanol; dichloromethane;

DOI:10.1021/jo00066a029

upstream raw materials:

1-O-Methyl-3-amino-3-C-methyl-4,6-O-benzyliden-2,3-didesoxy-α-D-arabino-hexopyranose

acetic anhydride

O^4',O^6'-(R)-benzylidene-O^1'-methyl-spiro[aziridine-2,3'-(α-D-arabino-2,3-dideoxy-hexopyranose)]

methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-methylene-α-D-erythro-hexopyranoside

Downstream raw materials:

methyl 3-acetamido-4-O-benzoyl-6-bromo-2,3,6-trideoxy-3-C-methyl-α-D-arabino-hexopyranoside

methyl 3-acetamido-4-O-benzoyl-2,3,6-trideoxy-3-C-methyl-α-D-ribo-hexopyranoside

D-rubranitrose

methyl 3-acetamido-4-O-benzoyl-2,3,6-trideoxy-6-iodo-3-C-methyl-α-D-ribo-hexopyranoside