methyl 3-O-benzyl-4,6-O-benzylidene-2-O-(2',3'-epoxypropyl)-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 3-O-benzyl-4,6-O-benzylidene-2-O-(2',3'-epoxypropyl)-α-D-glucopyranoside
• CAS No.: 189240-81-1
• Molecular Formula: C₂₄H₂₈O₇
• Molecular Weight: 428.482
• Mol file: 189240-81-1.mol

Synonyms:methyl 3-O-benzyl-4,6-O-benzylidene-2-O-(2',3'-epoxypropyl)-α-D-glucopyranoside

Chemical Property of methyl 3-O-benzyl-4,6-O-benzylidene-2-O-(2',3'-epoxypropyl)-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3-O-benzyl-4,6-O-benzylidene-2-O-(2',3'-epoxypropyl)-α-D-glucopyranoside

There total 2 articles about methyl 3-O-benzyl-4,6-O-benzylidene-2-O-(2',3'-epoxypropyl)-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: 37.0%

methyl 3-O-benzyl-4,6-O-benzylidene-D-glucopyranoside + 1,2-Epoxy-3-bromopropane (3132-64-7,82584-73-4) → methyl 3-O-benzyl-4,6-O-benzylidene-2-O-(2',3'-epoxypropyl)-α-D-glucopyranoside (189240-81-1) + methyl 3-O-benzyl-4,6-O-benzylidene-2-O-(2',3'-epoxypropyl)-β-D-glucopyranoside

Guidance literature:

With calcium sulfate; potassium hydroxide; In N,N-dimethyl-formamide; at 25 ℃; for 1.5h;

DOI:10.1080/07328309708006517

Reference yield:

methyl 3-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside (2774-19-8,14419-69-3,15887-67-9,23392-28-1,57539-08-9,61277-63-2,65877-21-6,74410-51-8,76419-48-2,80734-73-2,86363-44-2,89301-79-1,94061-92-4,94062-87-0,108739-92-0,129706-93-0,143005-12-3) + <<<(trifluoromethyl)sulfonyl>oxy>methyl>oxirane (95648-11-6) → methyl 3-O-benzyl-4,6-O-benzylidene-2-O-(2',3'-epoxypropyl)-α-D-glucopyranoside (189240-81-1)

Guidance literature:

With sodium hydride; Yield given. Multistep reaction; 1.) THF, RT, 30 min, 2.) THF, CH₂Cl₂, from -10 deg C to RT;

DOI:10.1016/0008-6215(94)84180-2

Reference yield: 94.0%

methyl 3-O-benzyl-4,6-O-benzylidene-2-O-(2',3'-epoxypropyl)-α-D-glucopyranoside (189240-81-1) → methyl 2-O-(2'-hydroxypropyl)-α-D-glucopyranoside + methyl 4,6-O-benzylidene-2-O-(2'-hydroxypropyl)-α-D-glucopyranoside

Guidance literature:

With ammonium formate; palladium on activated charcoal; In methanol; for 2h; Heating;

DOI:10.1080/07328309708006517

upstream raw materials:

methyl 3-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside

<<<(trifluoromethyl)sulfonyl>oxy>methyl>oxirane

1,2-Epoxy-3-bromopropane

Downstream raw materials:

methyl 3-O-benzyl-2-O-(2,3-dihydroxypropyl)-α-D-glucopyranoside