4,6-O-Benzylidene-2-deoxy-3-O-methyl-α-D-arabino-hexopyranoside

Base Information

• Chemical Name: 4,6-O-Benzylidene-2-deoxy-3-O-methyl-α-D-arabino-hexopyranoside
• CAS No.: 126373-46-4
• Molecular Formula: C₁₅H₂₀O₅
• Molecular Weight: 280.321
• Mol file: 126373-46-4.mol

Synonyms:4,6-O-Benzylidene-2-deoxy-3-O-methyl-α-D-arabino-hexopyranoside

Chemical Property of 4,6-O-Benzylidene-2-deoxy-3-O-methyl-α-D-arabino-hexopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4,6-O-Benzylidene-2-deoxy-3-O-methyl-α-D-arabino-hexopyranoside

There total 13 articles about 4,6-O-Benzylidene-2-deoxy-3-O-methyl-α-D-arabino-hexopyranoside 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: 100.0%

methyl 2-deoxy-4,6-O-benzylidene-α-D-ribo-hexopyranoside (6752-48-3,16718-95-9,18424-62-9,19877-02-2,22886-97-1,52153-29-4,52612-68-7,55331-65-2,64978-95-6,65725-24-8,66512-93-4,67968-51-8,72904-80-4,77481-69-7,131615-73-1,138663-49-7,151214-39-0) + methyl iodide (74-88-4) → methyl-[O4,O6-((R)-benzylidene)-O3-methyl-α-D-ribo-2-deoxy-hexopyranoside] (21090-92-6,53131-18-3,66537-93-7,126373-46-4,135818-56-3,138663-50-0)

Guidance literature:

With sodium hydride; In tetrahydrofuran; for 4.5h; Cooling; Inert atmosphere;

DOI:10.1039/c2cc34404a

Reference yield: 98.0%

methyl 4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside (6752-48-3,16718-95-9,18424-62-9,19877-02-2,22886-97-1,52153-29-4,52612-68-7,55331-65-2,64978-95-6,65725-24-8,66512-93-4,67968-51-8,72904-80-4,77481-69-7,131615-73-1,138663-49-7,151214-39-0) + methyl iodide (74-88-4) → 4,6-O-Benzylidene-2-deoxy-3-O-methyl-α-D-arabino-hexopyranoside (126373-46-4)

Guidance literature:

methyl 4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; for 1h;

methyl iodide; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃;

DOI:10.1016/j.bmcl.2017.06.008

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → 4,6-O-Benzylidene-2-deoxy-3-O-methyl-α-D-arabino-hexopyranoside (126373-46-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 7 h / Molecular sieve

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 - 20 °C

2.2: 0 - 20 °C

With sodium hydride; toluene-4-sulfonic acid; In N,N-dimethyl-formamide; mineral oil;

DOI:10.1016/j.bmcl.2017.06.008

upstream raw materials:

methyl-[O⁴,O⁶-((S)-benzylidene)-α-D-xylo-2-deoxy-hexopyranoside]

methyl iodide

benzaldehyde

methyl-(α-D-xylo-2-deoxy-hexopyranoside)

Downstream raw materials:

4-O-acetyl-D-cymaropyranosyl ortho-hexynylbenzoate

methyl 4-O-(2,4-di-O-benzoyl-D-thevetopyranosyl)-β-D-cymaropyranoside

methyl 4-O-(2,4-di-O-benzoyl-D-thevetopyranosyl)-α-D-cymaropyranoside

Methyl 4-O-benzoyl-6-bromo-2,6-dideoxy-3-O-methyl-α-D-ribo-hexopyranoside