benzyl 2-acetamido-2-deoxy-3,6-di-O-pivaloyl-α-D-glucopyranoside

Base Information

• Chemical Name: benzyl 2-acetamido-2-deoxy-3,6-di-O-pivaloyl-α-D-glucopyranoside
• CAS No.: 206751-88-4
• Molecular Formula: C₂₅H₃₇NO₈
• Molecular Weight: 479.571
• Mol file: 206751-88-4.mol

Synonyms:benzyl 2-acetamido-2-deoxy-3,6-di-O-pivaloyl-α-D-glucopyranoside

Chemical Property of benzyl 2-acetamido-2-deoxy-3,6-di-O-pivaloyl-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 2-acetamido-2-deoxy-3,6-di-O-pivaloyl-α-D-glucopyranoside

There total 3 articles about benzyl 2-acetamido-2-deoxy-3,6-di-O-pivaloyl-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: 87.0%

pivaloyl chloride (3282-30-2) + benzyl 2-acetamido-2-deoxy-α-D-glucopyranoside (13343-62-9,347411-88-5) → benzyl 2-acetamido-2-deoxy-3,6-di-O-pivaloyl-α-D-glucopyranoside (206751-88-4)

Guidance literature:

With pyridine; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1016/S0008-6215(97)10017-9

Reference yield:

N-Acetyl-D-glucosamine (7512-17-6,72-87-7,1136-42-1,1136-44-3,6082-29-7,6730-06-9,7772-94-3,10036-64-3,14131-60-3,14131-64-7,14131-68-1,14215-68-0,62057-49-2,62057-50-5,62057-51-6,62057-52-7,62057-53-8,62057-54-9,62057-55-0,62057-56-1,62075-50-7,62137-54-6,134451-97-1,134522-12-6,148347-16-4) → benzyl 2-acetamido-2-deoxy-3,6-di-O-pivaloyl-α-D-glucopyranoside (206751-88-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / BF₃*Et₂O / 5 h / 90 °C

2: 70 percent / pyridine / CH₂Cl₂ / 2 h / 0 °C

With pyridine; boron trifluoride diethyl etherate; In dichloromethane;

DOI:10.1016/S0960-894X(03)00287-7

Reference yield:

benzyl alcohol (100-51-6,185532-71-2) → benzyl 2-acetamido-2-deoxy-3,6-di-O-pivaloyl-α-D-glucopyranoside (206751-88-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / BF₃*Et₂O / 5 h / 90 °C

2: 70 percent / pyridine / CH₂Cl₂ / 2 h / 0 °C

With pyridine; boron trifluoride diethyl etherate; In dichloromethane;

DOI:10.1016/S0960-894X(03)00287-7

upstream raw materials:

pivaloyl chloride

benzyl 2-acetamido-2-deoxy-α-D-glucopyranoside

N-Acetyl-D-glucosamine

benzyl alcohol

Downstream raw materials:

benzyl 2-acetamido-2-deoxy-3,6-di-O-pivaloyl-α-D-xylo-hexopyranoside-4-ulose

benzyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-α-D-galactopyranoside

2,2-Dimethyl-propionic acid (2R,3R,4R,5R,6R)-3-acetylamino-2-(bis-benzyloxy-phosphoryloxy)-5-(2,2-dimethyl-propionyloxy)-6-methoxymethyl-tetrahydro-pyran-4-yl ester

2,2-Dimethyl-propionic acid (2R,3R,4R,5R,6R)-5-acetylamino-6-(bis-benzyloxy-phosphoryloxy)-2-(2,2-dimethyl-propionyloxymethyl)-4-methoxy-tetrahydro-pyran-3-yl ester