methyl 2-acetamido-3-O-acetyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 2-acetamido-3-O-acetyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside
• CAS No.: 6748-94-3
• Molecular Formula: C₁₈H₂₃NO₇
• Molecular Weight: 365.383
• Mol file: 6748-94-3.mol

Synonyms:methyl 2-acetamido-3-O-acetyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside

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

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about methyl 2-acetamido-3-O-acetyl-4,6-O-benzylidene-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: 97.0%

acetic anhydride (108-24-7) + N-((4aR,6S,7R,8R,8aS)-8-Hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-acetamide (6619-04-1) → methyl 2-acetamido-3-O-acetyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside (6748-94-3)

Guidance literature:

With pyridine; dmap; at 23 ℃; for 2h;

DOI:10.1002/anie.200906055

Reference yield: 76.0%

benzaldehyde dimethyl acetal (1125-88-8) + acetic anhydride (108-24-7) + methyl 2-acetylamido-2-deoxy-D-glucoside (6082-04-8) → methyl 2-acetamido-3-O-acetyl-4,6-di-O-benzylidene-2-deoxy-α-D-glucopyranoside (6748-94-3,35439-46-4,52885-38-8,78216-84-9,98574-00-6,99944-67-9,109121-60-0,109121-61-1,110658-08-7,128657-65-8,129784-18-5,139894-30-7,87303-57-9)

Guidance literature:

benzaldehyde dimethyl acetal; methyl 2-acetylamido-2-deoxy-D-glucoside; With toluene-4-sulfonic acid; In acetonitrile; at 25 ℃; Inert atmosphere;

acetic anhydride; In acetonitrile; at 40 ℃; Inert atmosphere;

DOI:10.1055/s-0028-1087913

Reference yield:

methyl 2,3-anhydro-4,6-dioxabenzylidene-α-D-gulopyranose (2880-96-8,3150-15-0,3150-16-1,3257-59-8,14187-71-4,15384-57-3,19465-13-5,32976-15-1,52885-37-7,53270-02-3,53270-03-4,65391-11-9,65391-12-0,66537-92-6,67226-04-4,71184-14-0,86420-78-2,86420-79-3,91177-51-4,91177-52-5,117708-93-7,120408-72-2) → methyl-[O3-acetyl-2-acetylamino-O4,O6-((S)-benzylidene)-2-deoxy-α-D-idopyranoside] (6748-94-3,35439-46-4,52885-38-8,78216-84-9,87303-57-9,98574-00-6,99944-67-9,109121-60-0,109121-61-1,110658-08-7,128657-65-8,129784-18-5,139894-30-7)

Guidance literature:

With ammonium hydroxide; at 120 ℃; Behandeln des Reaktionsprodukts mit Acetanhydrid und Pyridin;

DOI:10.1021/ja01241a003 DOI:10.1039/jr9600003392

upstream raw materials:

acetic anhydride

N-((4aR,6S,7R,8R,8aS)-8-Hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-acetamide

N-Acetyl-D-glucosamine

methyl 2,3-anhydro-4,6-dioxabenzylidene-α-D-gulopyranose

Downstream raw materials:

methyl 2-acetamido-3-O-acetyl-4-O-benzoyl-6-bromo-2,6-dideoxy-α-D-glucopyranoside

N-((4aR,6S,7R,8R,8aS)-8-Hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-acetamide

methyl-[2-acetylamino-O⁴,O⁶-((R)-benzylidene)-2-deoxy-α-D-altropyranoside]

methyl O-α-D-galactopyranosyl-(1<*>3)-2-acetamido-2-deoxy-α-D-glucopyranoside