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

Base Information

• Chemical Name: (R)-2,3-epoxypropyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
• CAS No.: 321679-22-5
• Molecular Formula: C₁₈H₂₃NO₇
• Molecular Weight: 365.383
• Mol file: 321679-22-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about (R)-2,3-epoxypropyl 2-acetamido-4,6-O-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:

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) → (R)-2,3-epoxypropyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside (321679-22-5) + N-[(2R,4aR,6R,7R,8R,8aS)-8-Hydroxy-6-((S)-1-oxiranylmethoxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 10 ℃; for 48h;

DOI:10.1016/S0957-4166(02)00649-3

Reference yield:

allyl 2-acetamido-2-deoxy-β-D-glucopyranoside (54400-75-8,64650-83-5,88903-97-3,116347-86-5,140849-88-3,144300-01-6,54400-77-0) → (R)-2,3-epoxypropyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside (321679-22-5)

Guidance literature:

Multi-step reaction with 2 steps

1: ZnCl₂ / 48 h

2: m-chloroperoxybenzoic acid / CH₂Cl₂ / 48 h / 10 °C

With 3-chloro-benzenecarboperoxoic acid; zinc(II) chloride; In dichloromethane;

DOI:10.1016/S0957-4166(02)00649-3

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) → (R)-2,3-epoxypropyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside (321679-22-5)

Guidance literature:

Multi-step reaction with 3 steps

1: NaOMe / methanol / 0.5 h / 20 °C

2: ZnCl₂ / 48 h

3: m-chloroperoxybenzoic acid / CH₂Cl₂ / 48 h / 10 °C

With sodium methylate; 3-chloro-benzenecarboperoxoic acid; zinc(II) chloride; In methanol; dichloromethane;

DOI:10.1016/S0957-4166(02)00649-3

upstream raw materials:

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

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

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

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester

Downstream raw materials:

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