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

Base Information

• Chemical Name: methyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O--α-D-glucopyranoside
• CAS No.: 100638-83-3
• Molecular Formula: C₁₈H₂₃NO₆S₂
• Molecular Weight: 413.516
• Mol file: 100638-83-3.mol

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

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

Chemical Property:

Purity/Quality:

Methyl2-(Acetylamino)-2-deoxy-4,6-O-(phenylmethylene)-α-D-glucopyranoside3-(S-MethylCarbonodithioate) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Methyl 2-(Acetylamino)-2-deoxy-4,6-O-(phenylmethylene)-α-D-glucopyranoside 3-(S-Methyl Carbonodithioate) is an intermediate used in the synthesis of 2,6-Diamino-2,3,6-trideoxy-D-ribo-Hexose Dihydrochloride (D416795), which is a degradent of Tobramycin (T524000) a single factor antibiotic comprising about 10% of nebramycin, the aminoglycosidic antibiotic complex produced by Streptomyces tenebrarius. Antibacterial.

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

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

carbon disulfide (75-15-0,12122-00-8) + methyl N-acetyl-2-amino-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside (6619-02-9,6619-04-1,10300-76-2,16727-56-3,17327-07-0,28978-56-5,52885-36-6,52885-45-7,78216-83-8,78513-50-5,87038-18-4,88295-36-7,110508-78-6,113159-04-9,117064-54-7,128657-61-4,129784-17-4,137330-28-0,78216-82-7) + methyl iodide (74-88-4) → methyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O--α-D-glucopyranoside (100638-83-3)

Guidance literature:

With 1H-imidazole; sodium hydride; Yield given. Multistep reaction;

Reference yield: 99.0%

methyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O--α-D-glucopyranoside (100638-83-3) → methyl 2-(acetylamino)-2,3-dideoxy-4,6-O-(phenylmethylene)-α-D-ribo-hexopyranoside (93453-17-9)

Guidance literature:

With azobisisobutyronitrile; tri-n-butyl-tin hydride; In toluene; for 0.0833333h;

DOI:10.1246/bcsj.60.255

Reference yield: 85.0%

methyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O--α-D-glucopyranoside (100638-83-3) → methyl 2-(acetylamino)-2,3-dideoxy-4,6-O-(phenylmethylene)-α-D-ribo-hexopyranoside (93453-17-9) + methyl N-acetyl-2-amino-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside (6619-02-9,6619-04-1,10300-76-2,16727-56-3,17327-07-0,28978-56-5,52885-36-6,52885-45-7,78216-83-8,78513-50-5,87038-18-4,88295-36-7,110508-78-6,113159-04-9,117064-54-7,128657-61-4,129784-17-4,137330-28-0,78216-82-7)

Guidance literature:

With tri-n-butyl-tin hydride; In toluene; Heating;

upstream raw materials:

carbon disulfide

methyl N-acetyl-2-amino-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside

methyl iodide

Downstream raw materials:

methyl 2-(acetylamino)-2,3-dideoxy-4,6-O-(phenylmethylene)-α-D-ribo-hexopyranoside

methyl N-acetyl-2-amino-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside