4-Methoxybenzyl beta-D-glucopyranoside

Base Information

• Chemical Name: 4-Methoxybenzyl beta-D-glucopyranoside
• CAS No.: 81381-72-8
• Molecular Formula: C14H20O7
• Molecular Weight: 300.309
• DSSTox Substance ID: DTXSID801261572
• Nikkaji Number: J1.005.433H
• Wikidata: Q105015713
• Mol file: 81381-72-8.mol

Synonyms:4-Methoxybenzyl beta-D-glucopyranoside;81381-72-8;(4-Methoxyphenyl)methylbeta-D-glucopyranoside;SCHEMBL5787376;DTXSID801261572;(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(4-methoxyphenyl)methoxy]oxane-3,4,5-triol

Chemical Property of 4-Methoxybenzyl beta-D-glucopyranoside

Chemical Property:

• PSA: 108.61000
• Density: 1.40
• LogP: -0.98830
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 300.12090297
• Heavy Atom Count: 21
• Complexity: 306

Purity/Quality:

99% ^*data from raw suppliers

(4-Methoxyphenyl)methylbeta-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)COC2C(C(C(C(O2)CO)O)O)O
• Isomeric SMILES: COC1=CC=C(C=C1)CO[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O

Technology Process of 4-Methoxybenzyl beta-D-glucopyranoside

There total 13 articles about 4-Methoxybenzyl beta-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: 96.0%

4-Methoxybenzyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (141263-06-1) → paramethoxybenzyl β-D-galactopyranoside (81381-72-8,113788-54-8)

Guidance literature:

With triethylamine; In methanol; water; for 20h; Ambient temperature;

DOI:10.1016/S0040-4039(00)78500-5

Reference yield: 92.0%

(4-methoxybenzyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (171412-20-7) → (4-methoxyphenyl)methyl-β-D-glucopyranoside (81381-72-8)

Guidance literature:

With methanol; sodium methylate; at 20 ℃; for 2h;

DOI:10.1248/cpb.58.1627

Reference yield: 26.0%

β-D-glucose (492-61-5) + 4-Methoxybenzyl alcohol (105-13-5) → (4-methoxyphenyl)methyl-β-D-glucopyranoside (81381-72-8)

Guidance literature:

With Prunus domestica prune seed meal; at 50 ℃; for 50h; pH=6; aq. phosphate buffer; Ionic liquid; Enzymatic reaction;

DOI:10.1016/j.molcatb.2011.08.009

upstream raw materials:

4-Methoxybenzyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside

4-Methoxybenzyl alcohol

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate

Downstream raw materials:

4-methoxybenzyl 4,6-O-benzylidene-β-D-glucopyranoside

4-Methoxybenzyl 2,4,6-tri-O-acetyl-3-O-allyl-β-d-galactopyranoside

p-methoxybenzyl 2,3,4,6-tetra-O-allyl-β-D-galactopyranoside

paramethoxybenzyl 6-O-terbutyldimethylsilyl β-D-galactopyranoside

Refernces

• 1、 Zhou, Youzhi,Zhao, Lu,Liu, Ke,Zhang, Jinsong,Chu, Jianlin,He, Bingfang. "A novel strategy to improve the aromatic alcohols tolerance of enzyme for preparative-scale synthesis of natural glycosides". . p. 9 - 12. Retrieved 2017/08/22.
• 2、 -. "HYDROLASE ENZYME SUBSTRATES AND USES THEREOF". Page/Page column 64. . Retrieved 2012/08/07.