phenyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1→6)-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: phenyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1→6)-1-thio-β-D-glucopyranoside
• CAS No.: 1439813-22-5
• Molecular Formula: C₄₆H₄₂O₁₄S
• Molecular Weight: 850.897

Synonyms:phenyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1→6)-1-thio-β-D-glucopyranoside

Chemical Property of phenyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1→6)-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

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Technology Process of phenyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1→6)-1-thio-β-D-glucopyranoside

There total 2 articles about phenyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1→6)-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%

2,3,4,6-tetra-O-benzoylglucosyl bromide (14218-11-2) + C20H32O5SSn → phenyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1→6)-1-thio-β-D-glucopyranoside (1439813-22-5)

Guidance literature:

2,3,4,6-tetra-O-benzoylglucosyl bromide; C₂₀H₃₂O₅SSn; In dichloromethane; at -30 ℃; for 0.5h; Inert atmosphere; Molecular sieve;

With silver trifluoromethanesulfonate; In dichloromethane; at 10 ℃; for 6h; Reagent/catalyst; Time; regioselective reaction; Inert atmosphere; Molecular sieve; Darkness;

DOI:10.1002/ejoc.201300026

Reference yield:

(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol (2936-70-1,5624-48-6,13992-15-9,16758-34-2,28244-97-5,77481-62-0,77481-63-1,105088-17-3,149495-84-1) → phenyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1→6)-1-thio-β-D-glucopyranoside (1439813-22-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: methanol / 3 h / Reflux; Inert atmosphere

2.1: dichloromethane / 0.5 h / -30 °C / Inert atmosphere; Molecular sieve

2.2: 6 h / 10 °C / Inert atmosphere; Molecular sieve; Darkness

In methanol; dichloromethane;

DOI:10.1002/ejoc.201300026

Reference yield: 80.0%

phenyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1→6)-1-thio-β-D-glucopyranoside (1439813-22-5) + benzoyl chloride (98-88-4) → phenyl 6-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1→6)-2,3,4-tetra-O-benzoyl-β-D-glucopyranoside (216006-43-8)

Guidance literature:

With pyridine; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1002/ejoc.201300026

upstream raw materials:

(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol

2,3,4,6-tetra-O-benzoylglucosyl bromide

Downstream raw materials:

phenyl 6-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1→6)-2,3,4-tetra-O-benzoyl-β-D-glucopyranoside

C₆₁H₄₉BrO₁₇

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