3-O-[2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-3,4-di-O-benzyl-α-D-glucopyranosyl]-sn-glycerol

Base Information

• Chemical Name: 3-O-[2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-3,4-di-O-benzyl-α-D-glucopyranosyl]-sn-glycerol
• CAS No.: 208656-51-3
• Molecular Formula: C₅₇H₆₄O₁₃
• Molecular Weight: 957.127
• Mol file: 208656-51-3.mol

Synonyms:3-O-[2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-3,4-di-O-benzyl-α-D-glucopyranosyl]-sn-glycerol

Chemical Property of 3-O-[2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-3,4-di-O-benzyl-α-D-glucopyranosyl]-sn-glycerol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-[2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-3,4-di-O-benzyl-α-D-glucopyranosyl]-sn-glycerol

There total 5 articles about 3-O-[2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-3,4-di-O-benzyl-α-D-glucopyranosyl]-sn-glycerol 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: 99.0%

3-O-[2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-3,4-di-O-benzyl-α-D-glucopyranosyl]-1,2-O-isopropylidene-sn-glycerol (313948-50-4) → 3-O-[2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-3,4-di-O-benzyl-α-D-glucopyranosyl]-sn-glycerol (208656-51-3)

Guidance literature:

With hydrogenchloride; In methanol; toluene; at 20 ℃; for 23h;

DOI:10.1016/S0040-4020(00)00793-6

Reference yield:

[(2R,3R,4S,5R,6S)-3,4-Bis-benzyloxy-6-fluoro-5-((3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethoxy]-tert-butyl-dimethyl-silane → 3-O-[2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-3,4-di-O-benzyl-α-D-glucopyranosyl]-sn-glycerol (208656-51-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 59 percent / n-Bu₄NF / tetrahydrofuran / 23 h / 20 °C

2: 86 percent / imidazole / dimethylformamide / 5 h / 20 °C

3: AgClO₄; SnCl₂; 2,6-di-tert-butylpyridine / diethyl ether / 40 h / 50 °C

4: 86 percent / n-Bu₄NF / tetrahydrofuran / 5 h / 20 °C

5: 99 percent / aq. HCl / methanol; toluene / 23 h / 20 °C

With 1H-imidazole; hydrogenchloride; 2,6-di-tert-butyl-pyridine; tetrabutyl ammonium fluoride; silver perchlorate; tin(ll) chloride; In tetrahydrofuran; methanol; diethyl ether; N,N-dimethyl-formamide; toluene; 1: desilylation / 2: silylation / 3: Substitution / 4: desilylation / 5: Hydrolysis;

DOI:10.1016/S0040-4020(00)00793-6

Reference yield:

2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-3,4-di-O-benzyl-β-D-glucopyranosyl fluoride (313948-55-9) → 3-O-[2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-3,4-di-O-benzyl-α-D-glucopyranosyl]-sn-glycerol (208656-51-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 86 percent / imidazole / dimethylformamide / 5 h / 20 °C

2: AgClO₄; SnCl₂; 2,6-di-tert-butylpyridine / diethyl ether / 40 h / 50 °C

3: 86 percent / n-Bu₄NF / tetrahydrofuran / 5 h / 20 °C

4: 99 percent / aq. HCl / methanol; toluene / 23 h / 20 °C

With 1H-imidazole; hydrogenchloride; 2,6-di-tert-butyl-pyridine; tetrabutyl ammonium fluoride; silver perchlorate; tin(ll) chloride; In tetrahydrofuran; methanol; diethyl ether; N,N-dimethyl-formamide; toluene; 1: silylation / 2: Substitution / 3: desilylation / 4: Hydrolysis;

DOI:10.1016/S0040-4020(00)00793-6

upstream raw materials:

3-O-[2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-3,4-di-O-benzyl-α-D-glucopyranosyl]-1,2-O-isopropylidene-sn-glycerol

2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-3,4-di-O-benzyl-β-D-glucopyranosyl fluoride

2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-3,4-di-O-benzyl-6-O-tert-butyldimethylsilyl-β-D-glucopyranosyl fluoride

3-O-[2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-3,4-di-O-benzyl-6-O-tert-butyldimethylsilyl-α-D-glucopyranosyl]-1,2-O-isopropylidene-sn-glycerol