benzyl 2-acetamido-4,6-O-benzylidene-3-O-[(R)-1-carboxyethyl]-2-deoxy-α-D-glucopyranoside

Base Information

• Chemical Name: benzyl 2-acetamido-4,6-O-benzylidene-3-O-[(R)-1-carboxyethyl]-2-deoxy-α-D-glucopyranoside
• CAS No.: 73089-68-6
• Molecular Formula: C₂₅H₂₉NO₈
• Molecular Weight: 471.507
• Mol file: 73089-68-6.mol

Synonyms:benzyl 2-acetamido-4,6-O-benzylidene-3-O-[(R)-1-carboxyethyl]-2-deoxy-α-D-glucopyranoside

Chemical Property of benzyl 2-acetamido-4,6-O-benzylidene-3-O-[(R)-1-carboxyethyl]-2-deoxy-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 2-acetamido-4,6-O-benzylidene-3-O-[(R)-1-carboxyethyl]-2-deoxy-α-D-glucopyranoside

There total 9 articles about benzyl 2-acetamido-4,6-O-benzylidene-3-O-[(R)-1-carboxyethyl]-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: 94.0%

benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside (78246-81-8) + (S)-2-chloropropanoic acid (29617-66-1) → benzyl 2-acetamido-4,6-O-benzylidene-3-O-[(R)-1-carboxyethyl]-2-deoxy-α-D-glucopyranoside (73089-68-6)

Guidance literature:

benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside; With sodium hydride; In 1,4-dioxane; mineral oil; at 60 ℃; for 0.0833333h; Inert atmosphere;

(S)-2-chloropropanoic acid; In 1,4-dioxane; mineral oil; at 60 ℃; for 16.5h; Inert atmosphere;

DOI:10.1002/chem.201604279

Reference yield: 85.0%

benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside (78246-81-8) + (R)-2-chloropropionic acid (7474-05-7) → benzyl 2-acetamido-4,6-O-benzylidene-3-O-[(R)-1-carboxyethyl]-2-deoxy-α-D-glucopyranoside (73089-68-6)

Guidance literature:

With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; at 70 ℃; for 18h;

Reference yield:

benzyl 2-acetamido-2-deoxy-α-D-glucopyranoside (13343-62-9,347411-88-5) → benzyl 2-acetamido-4,6-O-benzylidene-3-O-[(R)-1-carboxyethyl]-2-deoxy-α-D-glucopyranoside (73089-68-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 95 percent / p-toluenesulfonic acid; triethyl ortoformate / dimethylformamide; dioxane / 20 h / 20 °C

2.1: NaH / dioxane / 2 h / 95 °C

2.2: 80 percent / dioxane / 3 h / 60 °C

With sodium hydride; toluene-4-sulfonic acid; orthoformic acid triethyl ester; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1135/cccc20051615

upstream raw materials:

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

(R)-2-chloropropionic acid

(S)-2-chloropropanoic acid

benzyl alcohol

Downstream raw materials:

(R)-2-((2R,4aR,6S,7R,8R,8aS)-7-Acetylamino-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-propionic acid 2,2,2-trichloro-ethyl ester

benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-[(R)-1-(methoxycarbonyl)ethyl]-α-D-glucopyranoside

(S)-2-[(R)-2-((2R,4aR,6S,7R,8R,8aS)-7-Acetylamino-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-propionylamino]-propionic acid 2-benzenesulfonyl-ethyl ester

benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(D-1-{[2-(phenylsulfonyl)ethoxy]carbonyl}ethyl)-α-D-glucopyranoside