(2R)-2,3-dihydroxypropyl 2-acetamido-3-O-acetyl-4,6-O-(R)-benzylidene-2-deoxy-β-D-glucopyranoside

Base Information

• Chemical Name: (2R)-2,3-dihydroxypropyl 2-acetamido-3-O-acetyl-4,6-O-(R)-benzylidene-2-deoxy-β-D-glucopyranoside
• CAS No.: 1372788-84-5
• Molecular Formula: C₂₀H₂₇NO₉
• Molecular Weight: 425.436
• Mol file: 1372788-84-5.mol

Synonyms:(2R)-2,3-dihydroxypropyl 2-acetamido-3-O-acetyl-4,6-O-(R)-benzylidene-2-deoxy-β-D-glucopyranoside

Chemical Property of (2R)-2,3-dihydroxypropyl 2-acetamido-3-O-acetyl-4,6-O-(R)-benzylidene-2-deoxy-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R)-2,3-dihydroxypropyl 2-acetamido-3-O-acetyl-4,6-O-(R)-benzylidene-2-deoxy-β-D-glucopyranoside

There total 5 articles about (2R)-2,3-dihydroxypropyl 2-acetamido-3-O-acetyl-4,6-O-(R)-benzylidene-2-deoxy-β-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: 81.0%

allyl 2-acetamido-3-O-acetyl-(R)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside (508194-14-7) → (2R)-2,3-dihydroxypropyl 2-acetamido-3-O-acetyl-4,6-O-(R)-benzylidene-2-deoxy-β-D-glucopyranoside (1372788-84-5)

Guidance literature:

allyl 2-acetamido-3-O-acetyl-(R)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside; With osmium(VIII) oxide; N,N,N,N,-tetramethylethylenediamine; In dichloromethane; at -78 ℃; for 2h;

With ethylenediamine; In dichloromethane; at 20 ℃; for 48h; optical yield given as %de; diastereoselective reaction;

DOI:10.1002/ejoc.201101539

Reference yield:

allyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside (63064-48-2,116288-58-5,117299-90-8,126778-02-7,28738-44-5) → (2R)-2,3-dihydroxypropyl 2-acetamido-3-O-acetyl-4,6-O-(R)-benzylidene-2-deoxy-β-D-glucopyranoside (1372788-84-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium methylate / methanol / 0.5 h / 20 °C

1.2: Dowex 50 acidic resin / 20 °C

2.1: camphor-10-sulfonic acid / acetonitrile / 20 °C

3.1: dmap / dichloromethane / 3 h / 0 °C

4.1: osmium(VIII) oxide; N,N,N,N,-tetramethylethylenediamine / dichloromethane / 2 h / -78 °C

4.2: 48 h / 20 °C

With dmap; osmium(VIII) oxide; N,N,N,N,-tetramethylethylenediamine; camphor-10-sulfonic acid; sodium methylate; In methanol; dichloromethane; acetonitrile;

DOI:10.1002/ejoc.201101539

Reference yield:

allyl 2-acetamido-(R)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside (63064-49-3,65947-37-7,74984-84-2,88903-98-4,92841-84-4,116347-88-7,136845-44-8,138456-61-8,74984-83-1) → (2R)-2,3-dihydroxypropyl 2-acetamido-3-O-acetyl-4,6-O-(R)-benzylidene-2-deoxy-β-D-glucopyranoside (1372788-84-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dmap / dichloromethane / 3 h / 0 °C

2.1: osmium(VIII) oxide; N,N,N,N,-tetramethylethylenediamine / dichloromethane / 2 h / -78 °C

2.2: 48 h / 20 °C

With dmap; osmium(VIII) oxide; N,N,N,N,-tetramethylethylenediamine; In dichloromethane;

DOI:10.1002/ejoc.201101539

upstream raw materials:

allyl 2-acetamido-2-deoxy-β-D-glucopyranoside

allyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside

allyl 2-acetamido-3-O-acetyl-(R)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

allyl 2-acetamido-(R)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside