methyl 3-O-benzyl-β-D-xylopyranoside

Base Information

• Chemical Name: methyl 3-O-benzyl-β-D-xylopyranoside
• CAS No.: 72521-39-2
• Molecular Formula: C₁₃H₁₈O₅
• Molecular Weight: 254.283
• Mol file: 72521-39-2.mol

Synonyms:methyl 3-O-benzyl-β-D-xylopyranoside

Chemical Property of methyl 3-O-benzyl-β-D-xylopyranoside

Chemical Property:

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3-O-benzyl-β-D-xylopyranoside

There total 6 articles about methyl 3-O-benzyl-β-D-xylopyranoside 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 2,4-O-diacetyl-3-O-benzyl-β-D-xylopyranoside (74334-74-0) → methyl 3-O-benzyl-β-D-xylopyranoside (72521-39-2)

Guidance literature:

With sodium methylate; In methanol; at 40 ℃;

DOI:10.1002/cmdc.201200541

Reference yield:

benzyl bromide (100-39-0) + methyl-β-D-xylopyranoside (612-05-5) → methyl β-D-xylopyranoside 2-benzyl ether (51755-03-4) + methyl 3-O-benzyl-β-D-xylopyranoside (72521-39-2)

Guidance literature:

methyl-β-D-xylopyranoside; With 2,6-bis[(4R)-5,5-dihydro-4-phenyl-2-oxazolyl]pyridine; copper dichloride; In acetonitrile; at 20 ℃; for 0.333333h;

benzyl bromide; With tetrabutylammomium bromide; silver(l) oxide; In acetonitrile; at 40 ℃; for 4h; Overall yield = 40 percent; regioselective reaction;

DOI:10.1002/adsc.202101121

Reference yield:

benzyl bromide (100-39-0) + methyl-β-D-xylopyranoside (612-05-5) → methyl α-D-xylopyranoside 4-benzyl ether (69984-20-9) + methyl β-D-xylopyranoside 2-benzyl ether (51755-03-4) + methyl 3-O-benzyl-β-D-xylopyranoside (72521-39-2)

Guidance literature:

With tetrabutylammomium bromide; di(n-butyl)tin oxide; N-ethyl-N,N-diisopropylamine; In neat (no solvent); at 70 ℃; for 13h; Overall yield = ~ 50 %;

DOI:10.1021/jo402399n

upstream raw materials:

1,2,4-tri-O-acetyl-3-O-benzyl-α,β-D-xylopyranose

methyl 2,4-O-diacetyl-3-O-benzyl-β-D-xylopyranoside

Acetic acid (3R,4S,5R)-5-acetoxy-4-benzyloxy-2-bromo-tetrahydro-pyran-3-yl ester

benzyl bromide

Downstream raw materials:

(2R,3R,4S,5R)-4-Benzyloxy-2-methoxy-3,5-bis-trimethylsilanyloxy-tetrahydro-pyran

methyl 2,4-di-O-benzoyl-β-D-xylopyranoside

methyl N,3-O-dibenzyl-2,4-dideoxy-2,4-imino-L-ribonamide

C₁₉H₂₁NO₃