methyl 2-O-(p-methoxybenzyl)-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 2-O-(p-methoxybenzyl)-α-D-glucopyranoside
• CAS No.: 214068-12-9
• Molecular Formula: C₁₅H₂₂O₇
• Molecular Weight: 314.335
• Mol file: 214068-12-9.mol

Synonyms:methyl 2-O-(p-methoxybenzyl)-α-D-glucopyranoside

Chemical Property of methyl 2-O-(p-methoxybenzyl)-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-O-(p-methoxybenzyl)-α-D-glucopyranoside

There total 1 articles about methyl 2-O-(p-methoxybenzyl)-α-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: 98.0%

methyl 2-O-(p-methoxybenzyl)-4,6-O-(p-methoxybenzylidene)-α-D-glucopyranoside (214068-00-5) → methyl 2-O-(p-methoxybenzyl)-α-D-glucopyranoside (214068-12-9)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; for 1h; Ambient temperature;

DOI:10.1021/jo980501r

Reference yield: 94.0%

trityl chloride (76-83-5) + methyl 2-O-(p-methoxybenzyl)-α-D-glucopyranoside (214068-12-9) → methyl 2-O-(p-methoxybenzyl)-6-O-trityl-α-D-glucopyranoside (214068-17-4)

Guidance literature:

With dmap; triethylamine; In N,N-dimethyl-formamide; Ambient temperature; overnight;

DOI:10.1021/jo980501r

Reference yield:

methyl 2-O-(p-methoxybenzyl)-α-D-glucopyranoside (214068-12-9) → 1,3-myo-inosityl bis(phosphate) tetrasodium salt

Guidance literature:

Multi-step reaction with 12 steps

1: 94 percent / DMAP, Et₃N / dimethylformamide / Ambient temperature; overnight

2: NaH / dimethylformamide / 2 h / Ambient temperature

3: p-TsOH monohydrate / methanol / 1 h / Ambient temperature

4: (COCl)2, Et₃N / CH₂Cl₂; dimethylsulfoxide / -78 deg C to rt

5: K₂CO₃ / acetonitrile / Heating; overnight

6: 1.) Hg(OAc)2, 2.) NaCl / 1.) acetone, H₂O, 45 min, 2.) rt, 24 h

7: 81 percent / NaBH(OAc)3 / acetonitrile; acetic acid / 0.75 h / Ambient temperature

8: proton sponge, n-Bu₄NBr / acetonitrile / rt to 55 deg C

9: aq. NaOH / methanol / 2 h / Heating

10: 67 percent / DDQ / CH₂Cl₂; H₂O / 2 h / Ambient temperature

11: 1.) 1H-tetrazole, 2.) m-CPBA / 1.) CH₂Cl₂, rt, 1 h ,2.) -40 deg C, 0 deg C, 30 min, rt, 30 min

12: 50 mg / NaHCO₃, H₂ / Pd/C / butan-1-ol; H₂O / 5 h / 2585.7 Torr

With 1H-tetrazole; dmap; sodium hydroxide; oxalyl dichloride; Proton Sponge; mercury(II) diacetate; tetrabutylammomium bromide; hydrogen; sodium tris(acetoxy)borohydride; sodium hydride; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium chloride; palladium on activated charcoal; In methanol; dichloromethane; water; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; butan-1-ol;

DOI:10.1021/jo980501r

upstream raw materials:

methyl 2-O-(p-methoxybenzyl)-4,6-O-(p-methoxybenzylidene)-α-D-glucopyranoside

Downstream raw materials:

methyl 2-O-(p-methoxybenzyl)-6-O-trityl-α-D-glucopyranoside

(2S,3S,4S,5R,6S)-3,4-Bis-benzyloxy-6-methoxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carbaldehyde

methyl 3,4-di-O-benzyl-2-O-(p-methoxybenzyl)-α-D-glucopyranoside

Acetic acid (1R,3S,4R,5S,6R)-3,4-bis-benzyloxy-6-hydroxy-5-(4-methoxy-benzyloxy)-2-oxo-cyclohexyl ester