methyl 2-O-benzyl-6,7-dideoxy-3,4-bis-O-(p-methoxybenzyl)-α-D-gluco-hept-6-enopyranoside (1,5)

Base Information

• Chemical Name: methyl 2-O-benzyl-6,7-dideoxy-3,4-bis-O-(p-methoxybenzyl)-α-D-gluco-hept-6-enopyranoside (1,5)
• CAS No.: 162583-83-7
• Molecular Formula: C₃₁H₃₆O₇
• Molecular Weight: 520.623
• Mol file: 162583-83-7.mol

Synonyms:methyl 2-O-benzyl-6,7-dideoxy-3,4-bis-O-(p-methoxybenzyl)-α-D-gluco-hept-6-enopyranoside (1,5)

Chemical Property of methyl 2-O-benzyl-6,7-dideoxy-3,4-bis-O-(p-methoxybenzyl)-α-D-gluco-hept-6-enopyranoside (1,5)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-O-benzyl-6,7-dideoxy-3,4-bis-O-(p-methoxybenzyl)-α-D-gluco-hept-6-enopyranoside (1,5)

There total 12 articles about methyl 2-O-benzyl-6,7-dideoxy-3,4-bis-O-(p-methoxybenzyl)-α-D-gluco-hept-6-enopyranoside (1,5) 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: 86.0%

Methyltriphenylphosphonium bromide (1779-49-3) + methyl 2-O-benzyl-3,4-bis-O-(p-methoxybenzyl)-α-D-gluco-hexodialdopyranoside (1,5) (183170-36-7) → methyl 2-O-benzyl-6,7-dideoxy-3,4-bis-O-(p-methoxybenzyl)-α-D-gluco-hept-6-enopyranoside (1,5) (162583-83-7)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; for 1h; Ambient temperature;

DOI:10.1021/jo961158y

Reference yield:

p-Anisaldehyde dimethyl acetal (2186-92-7) → methyl 2-O-benzyl-6,7-dideoxy-3,4-bis-O-(p-methoxybenzyl)-α-D-gluco-hept-6-enopyranoside (1,5) (162583-83-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 84 percent / p-toluenesulfonic acid / dimethylformamide / 4 h / 70 °C

2: 1.) dibutyltin oxide, tetrabutylammonium iodide / 1.) MeCN, reflux, 2 h, 2.) MeCN, reflux, 16 h

3: 87 percent / NaH / dimethylformamide / 3 h / Ambient temperature

4: 1.) LiAlH₄, 2.) AlCl₃ / 1.) THF, reflux, 1 h, 2.) THF, reflux, 2.5 h

5: 1.) DMSO, oxalyl chloride, 2.) triethylamine / 1.) CH₂Cl₂, -60 deg C, 20 min, 2.) CH₂Cl₂, -60 deg C, 10 min

6: 86 percent / potassium tert-butoxide / tetrahydrofuran / 1 h / Ambient temperature

With lithium aluminium tetrahydride; aluminium trichloride; oxalyl dichloride; potassium tert-butylate; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jo961158y

Reference yield:

methyl-alpha-D-glucopyranoside (97-30-3) → methyl 2-O-benzyl-6,7-dideoxy-3,4-bis-O-(p-methoxybenzyl)-α-D-gluco-hept-6-enopyranoside (1,5) (162583-83-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 84 percent / p-toluenesulfonic acid / dimethylformamide / 4 h / 70 °C

2: 1.) dibutyltin oxide, tetrabutylammonium iodide / 1.) MeCN, reflux, 2 h, 2.) MeCN, reflux, 16 h

3: 87 percent / NaH / dimethylformamide / 3 h / Ambient temperature

4: 1.) LiAlH₄, 2.) AlCl₃ / 1.) THF, reflux, 1 h, 2.) THF, reflux, 2.5 h

5: 1.) DMSO, oxalyl chloride, 2.) triethylamine / 1.) CH₂Cl₂, -60 deg C, 20 min, 2.) CH₂Cl₂, -60 deg C, 10 min

6: 86 percent / potassium tert-butoxide / tetrahydrofuran / 1 h / Ambient temperature

With lithium aluminium tetrahydride; aluminium trichloride; oxalyl dichloride; potassium tert-butylate; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jo961158y

upstream raw materials:

Methyltriphenylphosphonium bromide

methyl 2-O-benzyl-3,4-bis-O-(p-methoxybenzyl)-α-D-gluco-hexodialdopyranoside (1,5)

methyl 4,6-O-para-methoxybenzylidene-α-D-glucopyranoside

p-Anisaldehyde dimethyl acetal

Downstream raw materials:

(1R,2S,3S,4R,5R)-3-(benzyloxy)-1,2,4-trihydroxy-5-vinylcyclopentane

(1R,2S,3R,4R,5R)-3,4-Bis-benzyloxy-5-hydroxymethyl-cyclopentane-1,2-diol

(1R,2S,3S,4R,5S)-3,4-bis(benzyloxy)-1,2-bis[(p-methoxybenzyl)oxy]-5-vinylcyclopentane

(1S,2R,3S,4S,5R)-2,3-Bis-benzyloxy-4,5-bis-(4-methoxy-benzyloxy)-cyclopentanecarbaldehyde