Methyl 2,3-di-O-benzyl-4-O-methyloxalyl-6-O-triphenylmethyl-α-D-glucopyranoside

Base Information

• Chemical Name: Methyl 2,3-di-O-benzyl-4-O-methyloxalyl-6-O-triphenylmethyl-α-D-glucopyranoside
• CAS No.: 162191-08-4
• Molecular Formula: C₄₃H₄₂O₉
• Molecular Weight: 702.801
• Mol file: 162191-08-4.mol

Synonyms:Methyl 2,3-di-O-benzyl-4-O-methyloxalyl-6-O-triphenylmethyl-α-D-glucopyranoside

Chemical Property of Methyl 2,3-di-O-benzyl-4-O-methyloxalyl-6-O-triphenylmethyl-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl 2,3-di-O-benzyl-4-O-methyloxalyl-6-O-triphenylmethyl-α-D-glucopyranoside

There total 1 articles about Methyl 2,3-di-O-benzyl-4-O-methyloxalyl-6-O-triphenylmethyl-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: 94.0%

(2R,3R,4S,5R,6S)-4,5-bis(benzyloxy)tetrahydro-6-methoxy-2-((trityloxy)methyl)-2H-pyran-3-ol (20231-38-3,20688-86-2,51842-20-7,51842-38-7,71756-38-2,74372-80-8,87326-91-8) + monomethyl oxalyl chloride (5781-53-3) → Methyl 2,3-di-O-benzyl-4-O-methyloxalyl-6-O-triphenylmethyl-α-D-glucopyranoside (162191-08-4)

Guidance literature:

With pyridine; dmap; for 15h; Ambient temperature;

Reference yield:

Methyl 2,3-di-O-benzyl-4-O-methyloxalyl-6-O-triphenylmethyl-α-D-glucopyranoside (162191-08-4) → Methyl 2,3-di-O-benzyl-4-deoxy-α-D-xylo-hexopyranoside (108164-50-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 20 percent / n-Bu₃SnH / AIBN / toluene / 5 h / Heating

2: 79 percent / 4-N,N-dimethylaminopyridine / acetonitrile / 24 h / 50 °C

3: 84 percent / aq. H₃PO₂, triethylamine / AIBN / dioxane / 3.5 h / Heating

4: 93 percent / aq. acetic acid / 0.5 h / 70 °C

With tri-n-butyl-tin hydride; hypophosphorous acid; acetic acid; triethylamine; dmap; 2,2'-azobis(isobutyronitrile); In 1,4-dioxane; toluene; acetonitrile;

Reference yield:

Methyl 2,3-di-O-benzyl-4-O-methyloxalyl-6-O-triphenylmethyl-α-D-glucopyranoside (162191-08-4) → Methyl 2,3-di-O-benzyl-4-deoxy-6-O-triphenylmethyl-α-D-xylo-hexopyranoside (162191-09-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 20 percent / n-Bu₃SnH / AIBN / toluene / 5 h / Heating

2: 79 percent / 4-N,N-dimethylaminopyridine / acetonitrile / 24 h / 50 °C

3: 84 percent / aq. H₃PO₂, triethylamine / AIBN / dioxane / 3.5 h / Heating

With tri-n-butyl-tin hydride; hypophosphorous acid; triethylamine; dmap; 2,2'-azobis(isobutyronitrile); In 1,4-dioxane; toluene; acetonitrile;

upstream raw materials:

(2R,3R,4S,5R,6S)-4,5-bis(benzyloxy)tetrahydro-6-methoxy-2-((trityloxy)methyl)-2H-pyran-3-ol

monomethyl oxalyl chloride

Downstream raw materials:

Methyl 2,3-di-O-benzyl-4-O-methanesulfonyl-6-O-triphenylmethyl-α-D-glucopyranoside

Methyl 2,3-di-O-benzyl-4-deoxy-α-D-xylo-hexopyranoside

(2R,3R,4R,5R,6S)-4,5-bis(benzyloxy)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3-yl methanesulfonate

Methyl 2,3-di-O-benzyl-4-deoxy-6-O-triphenylmethyl-α-D-xylo-hexopyranoside