methyl 4-O-benzyl-6-deoxy-4-C-(2,5-dimethoxybenzyl)-2,3-O-isopropylidene-α-L-talopyranoside

Base Information

• Chemical Name: methyl 4-O-benzyl-6-deoxy-4-C-(2,5-dimethoxybenzyl)-2,3-O-isopropylidene-α-L-talopyranoside
• CAS No.: 205810-92-0
• Molecular Formula: C₂₆H₃₄O₇
• Molecular Weight: 458.552
• Mol file: 205810-92-0.mol

Synonyms:methyl 4-O-benzyl-6-deoxy-4-C-(2,5-dimethoxybenzyl)-2,3-O-isopropylidene-α-L-talopyranoside

Chemical Property of methyl 4-O-benzyl-6-deoxy-4-C-(2,5-dimethoxybenzyl)-2,3-O-isopropylidene-α-L-talopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4-O-benzyl-6-deoxy-4-C-(2,5-dimethoxybenzyl)-2,3-O-isopropylidene-α-L-talopyranoside

There total 3 articles about methyl 4-O-benzyl-6-deoxy-4-C-(2,5-dimethoxybenzyl)-2,3-O-isopropylidene-α-L-talopyranoside 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: 98.1%

benzyl bromide (100-39-0) + methyl 6-deoxy-4-C-(2,5-dimethoxybenzyl)-2,3-O-isopropylidene-α-L-talopyranoside (205810-91-9) → methyl 4-O-benzyl-6-deoxy-4-C-(2,5-dimethoxybenzyl)-2,3-O-isopropylidene-α-L-talopyranoside (205810-92-0)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; for 22h; Heating;

DOI:10.1080/07328309808002326

Reference yield:

methyl 6-deoxy-2,3-O-isopropylidene-α-L-lyxo-hexopyranoside-4-ulose (2592-53-2) → methyl 4-O-benzyl-6-deoxy-4-C-(2,5-dimethoxybenzyl)-2,3-O-isopropylidene-α-L-talopyranoside (205810-92-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 53.4 percent / Li / tetrahydrofuran; diethyl ether; hexane / 1.) -70 deg C, 1 h, 2.) -70 deg C -> -30 deg C

2: 98.1 percent / NaH, Bu₄NI / tetrahydrofuran / 22 h / Heating

With tetra-(n-butyl)ammonium iodide; lithium; sodium hydride; In tetrahydrofuran; diethyl ether; hexane;

DOI:10.1080/07328309808002326

Reference yield:

2,5-dimethoxybenzyl ethyl ether → methyl 4-O-benzyl-6-deoxy-4-C-(2,5-dimethoxybenzyl)-2,3-O-isopropylidene-α-L-talopyranoside (205810-92-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 53.4 percent / Li / tetrahydrofuran; diethyl ether; hexane / 1.) -70 deg C, 1 h, 2.) -70 deg C -> -30 deg C

2: 98.1 percent / NaH, Bu₄NI / tetrahydrofuran / 22 h / Heating

With tetra-(n-butyl)ammonium iodide; lithium; sodium hydride; In tetrahydrofuran; diethyl ether; hexane;

DOI:10.1080/07328309808002326

upstream raw materials:

benzyl bromide

methyl 6-deoxy-4-C-(2,5-dimethoxybenzyl)-2,3-O-isopropylidene-α-L-talopyranoside

methyl 6-deoxy-2,3-O-isopropylidene-α-L-lyxo-hexopyranoside-4-ulose

Downstream raw materials:

methyl 4-O-benzyl-6-deoxy-4-C-(2,5-dimethoxybenzyl)-α-L-talopyranoside

methyl 4-O-benzyl-6-deoxy-4-C-(2,5-dimethoxybenzyl)-2,3-O-thiocarbonyl-α-L-talopyranoside

(2S,3S,6R)-3-Benzyloxy-3-(2,5-dimethoxy-benzyl)-6-methoxy-2-methyl-3,6-dihydro-2H-pyran