phenyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->4)-2-O-acetyl-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: phenyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->4)-2-O-acetyl-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside
• CAS No.: 299174-91-7
• Molecular Formula: C₆₂H₆₄O₁₁S
• Molecular Weight: 1017.25
• Mol file: 299174-91-7.mol

Synonyms:phenyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->4)-2-O-acetyl-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside

Chemical Property of phenyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->4)-2-O-acetyl-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->4)-2-O-acetyl-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside

There total 3 articles about phenyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->4)-2-O-acetyl-3,6-di-O-benzyl-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:

thiophenol (108-98-5) + 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-1,2-O-(1-methoxyethylidene)-α-D-glucopyranose (299174-88-2) → phenyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->4)-2-O-acetyl-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside (299174-91-7)

Guidance literature:

With mercury dibromide; In acetonitrile; at 65 ℃; for 3h;

DOI:10.1080/07328300008544113

Reference yield:

phenyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside (158198-56-2) → phenyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1->4)-2-O-acetyl-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside (299174-92-8) + phenyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->4)-2-O-acetyl-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside (299174-91-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: trifluoroacetic acid; triethylsilane / dichloromethane / 0 - 20 °C

2.1: 2-((trifluoromethyl)thio)benzo[d]isothiazol-3(2H)-one 1,1-dioxide / dichloromethane / 0.25 h / 20 °C / Molecular sieve; Inert atmosphere

2.2: 0.67 h / 0 - 20 °C / Molecular sieve; Inert atmosphere

With triethylsilane; 2-((trifluoromethyl)thio)benzo[d]isothiazol-3(2H)-one 1,1-dioxide; trifluoroacetic acid; In dichloromethane;

DOI:10.1039/d0ob01606c

Reference yield:

benzyl bromide (100-39-0) → phenyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->4)-2-O-acetyl-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside (299174-91-7)

Guidance literature:

Multi-step reaction with 2 steps

1: NaH / dimethylformamide / 2 h / 20 °C

2: 2.83 g / HgBr₂ / acetonitrile / 3 h / 65 °C

With sodium hydride; mercury dibromide; In N,N-dimethyl-formamide; acetonitrile; 1: Alkylation / 2: Ring cleavage;

DOI:10.1080/07328300008544113

upstream raw materials:

thiophenol

2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-1,2-O-(1-methoxyethylidene)-α-D-glucopyranose

benzyl bromide

phenyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside

Downstream raw materials:

phenyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside

phenyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-O-succinyl-1-thio-β-D-glucopyranoside