Phenyl 2,3-di-O-benzyl-6-O-(4-phenylbenzoyl)-4-O-(2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: Phenyl 2,3-di-O-benzyl-6-O-(4-phenylbenzoyl)-4-O-(2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside
• CAS No.: 250335-03-6
• Molecular Formula: C₆₆H₆₄O₁₁S
• Molecular Weight: 1065.29
• Mol file: 250335-03-6.mol

Synonyms:Phenyl 2,3-di-O-benzyl-6-O-(4-phenylbenzoyl)-4-O-(2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside

Chemical Property of Phenyl 2,3-di-O-benzyl-6-O-(4-phenylbenzoyl)-4-O-(2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Phenyl 2,3-di-O-benzyl-6-O-(4-phenylbenzoyl)-4-O-(2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside

There total 6 articles about Phenyl 2,3-di-O-benzyl-6-O-(4-phenylbenzoyl)-4-O-(2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-1-thio-β-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: 85.0%

Phenyl 2,3-di-O-benzyl-4-O-(4,6-di-O-benzylidene-2,3-di-O-benzyl-α-D-glucopyranosyl)-6-O-(4-phenylbenzoyl)-1-thio-β-D-glucopyranoside (309913-21-1) → Phenyl 2,3-di-O-benzyl-6-O-(4-phenylbenzoyl)-4-O-(2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside (250335-03-6)

Guidance literature:

With hydrogenchloride; 4 A molecular sieve; sodium cyanoborohydride; In diethyl ether; at 0 ℃; for 0.5h;

DOI:10.1055/s-2000-7601

Reference yield:

phenyl 4-O-(4,6-O-benzylidene-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside (87470-75-5) → Phenyl 2,3-di-O-benzyl-6-O-(4-phenylbenzoyl)-4-O-(2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside (250335-03-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 85 percent / imidazole / dimethylformamide / 0.75 h / 15 - 20 °C

2: 56 percent / aq. NaOH; Bu₄NHSO₄ / toluene / 72 h / 20 °C

3: 95 percent / TBAF / tetrahydrofuran / 1.5 h / 20 °C

4: 96 percent / DMAP / CH₂Cl₂ / 0.25 h / -10 - -7 °C

5: 85 percent / NaBH₃CN; molecular sieves 4 Angstroem; HCl / diethyl ether / 0.5 h / 0 °C

With 1H-imidazole; hydrogenchloride; dmap; sodium hydroxide; 4 A molecular sieve; tetrabutyl ammonium fluoride; tetra(n-butyl)ammonium hydrogensulfate; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; 1: Etherification / 2: Etherification / 3: Silyl ether cleavage / 4: Esterification / 5: Reduction;

DOI:10.1055/s-2000-7601

Reference yield:

phenyl 2I,3I,2II,3II-tetra-O-benzyl-4II,6II-O-benzylidene-1I-thio-β-maltoside (259742-19-3) → Phenyl 2,3-di-O-benzyl-6-O-(4-phenylbenzoyl)-4-O-(2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside (250335-03-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / DMAP / CH₂Cl₂ / 0.25 h / -10 - -7 °C

2: 85 percent / NaBH₃CN; molecular sieves 4 Angstroem; HCl / diethyl ether / 0.5 h / 0 °C

With hydrogenchloride; dmap; 4 A molecular sieve; sodium cyanoborohydride; In diethyl ether; dichloromethane; 1: Esterification / 2: Reduction;

DOI:10.1055/s-2000-7601

upstream raw materials:

Phenyl 2,3-di-O-benzyl-4-O-(4,6-di-O-benzylidene-2,3-di-O-benzyl-α-D-glucopyranosyl)-6-O-(4-phenylbenzoyl)-1-thio-β-D-glucopyranoside

phenyl 4-O-(4,6-O-benzylidene-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside

phenyl 2^I,3^I,2^II,3^II-tetra-O-benzyl-4^II,6^II-O-benzylidene-1^I-thio-β-maltoside

Phenyl 2,3,6-tri-O-acetyl-4-O-(2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glycopyranosyl)-1-thio-β-D-glucopyranoside