methyl 4,6-O-benzylidene-2-deoxy-2-C-(2-methyl-2-propenyl)-α-D-arabino-hexopyranosid-3-ulose

Base Information

• Chemical Name: methyl 4,6-O-benzylidene-2-deoxy-2-C-(2-methyl-2-propenyl)-α-D-arabino-hexopyranosid-3-ulose
• CAS No.: 217185-51-8
• Molecular Formula: C₁₈H₂₂O₅
• Molecular Weight: 318.37
• Mol file: 217185-51-8.mol

Synonyms:methyl 4,6-O-benzylidene-2-deoxy-2-C-(2-methyl-2-propenyl)-α-D-arabino-hexopyranosid-3-ulose

Chemical Property of methyl 4,6-O-benzylidene-2-deoxy-2-C-(2-methyl-2-propenyl)-α-D-arabino-hexopyranosid-3-ulose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4,6-O-benzylidene-2-deoxy-2-C-(2-methyl-2-propenyl)-α-D-arabino-hexopyranosid-3-ulose

There total 2 articles about methyl 4,6-O-benzylidene-2-deoxy-2-C-(2-methyl-2-propenyl)-α-D-arabino-hexopyranosid-3-ulose 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:

methyl 2,3-anhydro-4,6-benzylidene-α-D-allopyranoside (66537-92-6) → methyl 4,6-O-benzylidene-2-deoxy-2-C-(2-methyl-2-propenyl)-α-D-arabino-hexopyranosid-3-ulose (217185-51-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / tetrahydrofuran / 2 h / Heating

2: 1.) trifluoroacetic anhydride, dimethyl sulfoxide, 2.) triethylamine / 1.) CH₂Cl₂, -65 deg C, 1.5 h, 2.) CH₂Cl₂

With dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran;

DOI:10.1021/jo981225j

Reference yield:

methyl 4,6-O-benzylidene-2-deoxy-2-C-(2-methyl-2-propenyl)-α-D-altropyranoside (131681-34-0) → methyl 4,6-O-benzylidene-2-deoxy-2-C-(2-methyl-2-propenyl)-α-D-arabino-hexopyranosid-3-ulose (217185-51-8)

Guidance literature:

With dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; Yield given; Multistep reaction; 1.) CH₂Cl₂, -65 deg C, 1.5 h, 2.) CH₂Cl₂;

DOI:10.1021/jo981225j

Reference yield: 84.0%

methyl 4,6-O-benzylidene-2-deoxy-2-C-(2-methyl-2-propenyl)-α-D-arabino-hexopyranosid-3-ulose (217185-51-8) → methyl 4,6-O-benzylidene-2-deoxy-2-C-(2-methyl-2-propenyl)-α-D-erythro-hexopyranosid-3-ulose (217185-52-9)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; for 168h;

DOI:10.1021/jo981225j

upstream raw materials:

methyl 4,6-O-benzylidene-2-deoxy-2-C-(2-methyl-2-propenyl)-α-D-altropyranoside

methyl 2,3-anhydro-4,6-benzylidene-α-D-allopyranoside

Downstream raw materials:

methyl 4,6-O-benzylidene-2-deoxy-2-C-(2-methyl-2-propenyl)-α-D-erythro-hexopyranosid-3-ulose